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Results: 358 Rentals

  • Close to Road America and Beautiful Elkhart Lake and Great Golf Courses
    From $543 per night (USD)

    VRBO

    Close to Road America and Beautiful Elkhart Lake and Great Golf Courses

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    COME ENJOY ALL FOUR BEAUTIFUL SEASONS! The beautiful fall colors can be seen for miles and are accented with gorgeous su ...

    From $543 per night (USD)

    VRBO

    Details
  • Vacation In STYLE! 2 minutes to Road America, Beach, Golf, Downtown Elkhart Lake
    From $1015 per night (USD)

    Expedia

    Vacation In STYLE! 2 minutes to Road America, Beach, Golf, Downtown Elkhart Lake

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    Gorgeous home! Rustic design with 3900 sq. ft. open concept floor plan provides perfect space for everyone in your part ...

    From $1015 per night (USD)

    Expedia

    Details
  • 2021 Ryder Cup - Exceptional Location and Amenities.
    Click For Pricing

    VRBO

    2021 Ryder Cup - Exceptional Location and Amenities.

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    17 minutes (12.9 mi) from Whistling Straits in quiet neighborhood in Sheboygan Falls. 4 Bedroom, 3 Bath ranch home with ...

    Click For Pricing

    VRBO

    Details
  • Experience Wisconsin in an old farmhouse in the beautiful Kettle Moraine
    From $151 per night (USD)

    VRBO

    Experience Wisconsin in an old farmhouse in the beautiful Kettle Moraine

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    30

    My home sits on a 2 acre plot of land. It is in the country with lots of wildlife, trees, Trails, and a hill with a vie ...

    From $151 per night (USD)

    VRBO

    Details
  • Elkhart Lake lakeside cottage  53 mile drive to Lambeau Field and the 2025 draft
    From $580 per night (USD)

    VRBO

    Elkhart Lake lakeside cottage 53 mile drive to Lambeau Field and the 2025 draft

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    A 4 bedroom, 2 bath private home directly on the shore of beautiful Elkhart Lake. Two large living rooms, lovely lakefro ...

    From $580 per night (USD)

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    Details
  • 260 Feet of Sandy Lake Michigan Beachfront
    From $484 per night (USD)

    VRBO

    260 Feet of Sandy Lake Michigan Beachfront

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    Full on and private Lake Michigan water views abound at our historic family cottage, The Seagull Lodge. You’ll enjoy ex ...

    From $484 per night (USD)

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    Details
  • Just 75 steps from the sand and shore of Lake Michigan!
    From $667 per night (USD)

    VRBO

    Just 75 steps from the sand and shore of Lake Michigan!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    This listing is for the villa only. Blue Harbor water park passes are not included and currently unavailable to purchase ...

    From $667 per night (USD)

    VRBO

    Details
  • Unique Farmhouse located on a 22 acre Fish Farm
    From $477 per night (USD)

    Expedia

    Unique Farmhouse located on a 22 acre Fish Farm

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    This unique, open concept farm house is located on a 22 acre fish farm. The house and property is great for large group ...

    From $477 per night (USD)

    Expedia

    Details
  • Beautiful secluded house on 20 acres
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    VRBO

    Beautiful secluded house on 20 acres

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Beautiful secluded home on 20 acres, surrounded by woods. Quiet and private. Consist of 4 bedrooms, 2 half baths, and tw ...

    Click For Pricing

    VRBO

    Details
  • The Esker Ridge Chalet, Pristine Elkhart Solitude
    From $271 per night (USD)

    Expedia

    The Esker Ridge Chalet, Pristine Elkhart Solitude

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Experience the solitude and peace of the Kettle Moraine forest while remaining within walking distance of the beautiful ...

    From $271 per night (USD)

    Expedia

    Details
  • Serene Mid-Century Modern Lake Michigan Home .
    From $636 per night (USD)

    VRBO

    Serene Mid-Century Modern Lake Michigan Home .

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy the breathtaking sunrises and awe-inspiring views of Lake Michigan from this year-round home. The private and quie ...

    From $636 per night (USD)

    VRBO

    Details
  • Family Fun on Crystal Lake Island - minutes to  Road America, hiking, PGA Golf
    From $391 per night (USD)

    VRBO

    Family Fun on Crystal Lake Island - minutes to Road America, hiking, PGA Golf

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    **2022 calendar is open. Please note that our peak season rentals are a week minimum and run Monday-Monday** To reach K ...

    From $391 per night (USD)

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    Details
  • HD Acres - Rustic Retreat near Road America and Kohler Golf
    From $204 per night (USD)

    VRBO

    HD Acres - Rustic Retreat near Road America and Kohler Golf

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    A quarter-mile drive into the woods will bring you to our homestead that's situated on 40 acres that has it all -- ponds ...

    From $204 per night (USD)

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    Details
  • 3 Bedroom Beach House
    From $257 per night (USD)

    Expedia

    3 Bedroom Beach House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Three-bedroom house with full kitchen, dining room with spacious living room to watch movies, relax, play board games an ...

    From $257 per night (USD)

    Expedia

    Details
  • The Lakehouse on Long Lake
    From $503 per night (USD)

    VRBO

    The Lakehouse on Long Lake

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Our family always dreamt of owning a Lakehouse. When we had the opportunity to finally make that dream come true, we cra ...

    From $503 per night (USD)

    VRBO

    Details
  • REMODELED HOME ON LAKE MICHIGAN
    From $263 per night (USD)

    Expedia

    REMODELED HOME ON LAKE MICHIGAN

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    3 Bedrooms and 1.5 Baths in this two-story brick home. Located about one mile south of downtown Sheboygan on a bluff ove ...

    From $263 per night (USD)

    Expedia

    Details
  • Beautiful Country Home Near Popular Hot Spots!
    From $948 per night (USD)

    VRBO

    Beautiful Country Home Near Popular Hot Spots!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Stay in our spacious home, that includes two living rooms, as well as a bar area with darts, a pool table and foosball t ...

    From $948 per night (USD)

    VRBO

    Details
  • 5 Bedroom Modern House
    From $482 per night (USD)

    Expedia

    5 Bedroom Modern House

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    5 bedroom modern home. Full kitchen includes dishwasher, microwave, stove, fridge, keurig, everyday utensils and pans. P ...

    From $482 per night (USD)

    Expedia

    Details
  • Lake Orchard Farm Cottage
    From $791 per night (USD)

    VRBO

    Lake Orchard Farm Cottage

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    13

    Lake Orchard Farm Cottage is a 4 bedroom, 3 bathroom house with a full basement. Sleeps 12 comfortably (three queen beds ...

    From $791 per night (USD)

    VRBO

    Details
  • Updated Sheboygan Home w\/ Porch < 1 Mi to Beach
    From $271 per night (USD)

    Expedia

    Updated Sheboygan Home w\/ Porch < 1 Mi to Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Discover contemporary comfort right beside Lake Michigan’s coast with a trip to this 3-bedroom, 2-bathroom Sheboygan vac ...

    From $271 per night (USD)

    Expedia

    Details
  • Seagull Beach, Lake Michigan Cottage - Open for the NFL Draft  275\/night for 2-4
    From $202 per night (USD)

    VRBO

    Seagull Beach, Lake Michigan Cottage - Open for the NFL Draft 275\/night for 2-4

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    The whimsical little cottage has a spectacular view of the private beach, the woods and sunrises. Starting right at your ...

    From $202 per night (USD)

    VRBO

    Details
  • The River Bed - Condo sleeps 4 on west side
    From $176 per night (USD)

    VRBO

    The River Bed - Condo sleeps 4 on west side

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    5 minutes from Kohler & minutes from world class champion golf courses! Brand new & clean! Just completed condo with 2 ...

    From $176 per night (USD)

    VRBO

    Details
  • On the Shores of Lake Michigan with Breathtaking Views & A Beach Out Your Door!
    From $445 per night (USD)

    VRBO

    On the Shores of Lake Michigan with Breathtaking Views & A Beach Out Your Door!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Private and Charming Beach Bungalow located on a secluded road! Who said this is a lake? This feels more like an ocean ...

    From $445 per night (USD)

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    Details
  • Beautiful new year round Lake home on Long Lake in Kettle Moraine State forest
    From $428 per night (USD)

    Expedia

    Beautiful new year round Lake home on Long Lake in Kettle Moraine State forest

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Long Lake is a 432 Acre full recreational lake, known for water clarity, fishing, swimming, water skiing, boating , ice ...

    From $428 per night (USD)

    Expedia

    Details
  • Family Home, 1 Block to Lake Michigan Beach!
    From $367 per night (USD)

    VRBO

    Family Home, 1 Block to Lake Michigan Beach!

    Bedrooms:
    2
    Bathrooms:
    7
    Sleeps:
    7

    - Game Room - Central Location - Recently Remodeled From Lake Michigan to downtown, there's something for everyone at t ...

    From $367 per night (USD)

    VRBO

    Details
  • Lake House - Great stay for Road America, Kohler golf, & NFL Draft at Lambeau
    From $445 per night (USD)

    VRBO

    Lake House - Great stay for Road America, Kohler golf, & NFL Draft at Lambeau

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Master Bedroom - King Size Bed with view of the lake Second Bedroom - Two Twin Beds Third Bedroom - One Twin Bed 2 Pull ...

    From $445 per night (USD)

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    Details
  • Crystal Lake , WI Home  - Weekly Rental Available
    From $776 per night (USD)

    VRBO

    Crystal Lake , WI Home - Weekly Rental Available

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Rest and Relax in beautiful Wisconsin! 2 miles from Elkhart Lake Just steps from clear Crystal Lake, this luxury ...

    From $776 per night (USD)

    VRBO

    Details
  • Private Ranch home and great spot for Ryder Cup fans
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    Expedia

    Private Ranch home and great spot for Ryder Cup fans

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    9

    Our beautiful split bedroom ranch home is located on a quiet cul-de-sac and only minutes away from Whistling Straits. It ...

    Click For Pricing

    Expedia

    Details
  • Quiet and spacious home, close to downtown, the beach, and fantastic golfing.
    From $1283 per night (USD)

    VRBO

    Quiet and spacious home, close to downtown, the beach, and fantastic golfing.

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    Nestled on a wooded acre in a quiet cul de sac. The cozy wood burning fireplace and wet bar in the family room is great ...

    From $1283 per night (USD)

    VRBO

    Details
  • GUEST HOUSE SHORT WALK TO LAKE MICHIGAN\/Close to Downtown  & S Pier\n4bdrm 2 bath
    From $573 per night (USD)

    Expedia

    GUEST HOUSE SHORT WALK TO LAKE MICHIGAN\/Close to Downtown & S Pier\n4bdrm 2 bath

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    Amazing location just 3 blocks of Lake Michigan. a short walk to the public south beach, 2 min driving to the beach. 4 ...

    From $573 per night (USD)

    Expedia

    Details
  • A private, peaceful country home near Elkhart Lake
    From $400 per night (USD)

    VRBO

    A private, peaceful country home near Elkhart Lake

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    5

    Get away from it all in my quiet and very private country home near Elkhart Lake, WI. You'll be minutes away from Road A ...

    From $400 per night (USD)

    VRBO

    Details
  • Half mile from Road America! Perfect for NASCAR Race 2021 Includes Rec Room
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    Expedia

    Half mile from Road America! Perfect for NASCAR Race 2021 Includes Rec Room

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Lots of parking, washer and dryer on site for use with soap available. Full kitchen, spacious living room, fire pit, pat ...

    Click For Pricing

    Expedia

    Details
  •  5 BR IN PERFECT LOCATION FOR YOUR VACATION -walk to all
    From $511 per night (USD)

    VRBO

    5 BR IN PERFECT LOCATION FOR YOUR VACATION -walk to all

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    12

    Welcome! You are on your way to vacationing in Legendary Elkhart Lake. Our spacious house features an upper and lowe ...

    From $511 per night (USD)

    VRBO

    Details
  • Beautiful Remodeled Lake Michigan Beachfront Home Country Setting w\/ 500mbps int
    From $364 per night (USD)

    VRBO

    Beautiful Remodeled Lake Michigan Beachfront Home Country Setting w\/ 500mbps int

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    NOW we have 5000mbps internet speed! Yes you can now work from (my)Home! Spacious remodeled ranch with walk out baseme ...

    From $364 per night (USD)

    VRBO

    Details
  • A Short Walk to The Beach!
    From $631 per night (USD)

    VRBO

    A Short Walk to The Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Come and enjoy our little slice of paradise at the Victorian Inn. We completely remodeled our rooms in 2021. Our assoc ...

    From $631 per night (USD)

    VRBO

    Details
  • Heart of Elkhart Lake Condo-lower unit
    From $364 per night (USD)

    VRBO

    Heart of Elkhart Lake Condo-lower unit

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Step into the charm and elegance of a beautifully restored Victorian home, originally built around 1880. Located in the ...

    From $364 per night (USD)

    VRBO

    Details
  • Sheboygan Retreat in Black River
    From $264 per night (USD)

    VRBO

    Sheboygan Retreat in Black River

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Only an hour drive north of Milwaukee and south of Green Bay. Experience all Sheboygan County has to offer. Kohler gol ...

    From $264 per night (USD)

    VRBO

    Details
  • Walk to Road America! Lake House on Private Peninsula
    From $852 per night (USD)

    Expedia

    Walk to Road America! Lake House on Private Peninsula

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    Located on Little Elkhart Lake walking distance to Road America. Private 450' of waterfront on a peninsula with undevelo ...

    From $852 per night (USD)

    Expedia

    Details
  • Motorsport Villa - 3 minute drive to Road America & 15 to Whistling Straits.
    From $448 per night (USD)

    VRBO

    Motorsport Villa - 3 minute drive to Road America & 15 to Whistling Straits.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beautifully appointed second floor villa in the Motorsport Villa complex just 1 mile from famous Road America. Short 15 ...

    From $448 per night (USD)

    VRBO

    Details
  • Oostburg,WI Beach front, Lake Michigan
    From $528 per night (USD)

    Expedia

    Oostburg,WI Beach front, Lake Michigan

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    This rustic and charming 3 bedroom cottage has been in our family for over 100 years. It can sleep 7 adults plus we hav ...

    From $528 per night (USD)

    Expedia

    Details
  • This house puts you in the middle of ALL the Ryder Cup promotions!
    Click For Pricing

    VRBO

    This house puts you in the middle of ALL the Ryder Cup promotions!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    What separates this Ryder Cup Accommodation from others is not just its excellent location to the Village of Kohler (3.6 ...

    Click For Pricing

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    Details
  • Newly Remodeled Beachfront Home
    From $738 per night (USD)

    VRBO

    Newly Remodeled Beachfront Home

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    This 6 bedroom, gut-remodeled home was designed to provide comfort and privacy with families in mind. With 3 completely ...

    From $738 per night (USD)

    VRBO

    Details
  • Good Vibes on the Third Coast-Pet Friendly! Cozy and Close by!
    From $212 per night (USD)

    VRBO

    Good Vibes on the Third Coast-Pet Friendly! Cozy and Close by!

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    5

    Peaceful bohemian retreat filled with warmth and a lively vibe! Perfect for couples, remote workers, girls weekends, gol ...

    From $212 per night (USD)

    VRBO

    Details
  • Modern Cabin, private wooded lot with lake access
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    Expedia

    Modern Cabin, private wooded lot with lake access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Newly renovated home with grilling deck and fire pit. 600 foot walk to the beach. Brand new Kohler bathrooms, electric f ...

    Click For Pricing

    Expedia

    Details
  • Country Farmhouse 4 Miles from Road America and 45 Minutes from Green Bay
    From $1071 per night (USD)

    VRBO

    Country Farmhouse 4 Miles from Road America and 45 Minutes from Green Bay

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    15

    Quiet country atmosphere away from city noise and lights. Renovated in 2021. Two-plus car garage - plenty of room for s ...

    From $1071 per night (USD)

    VRBO

    Details
  • Private Ranch home hidden in the woods with lots of wildlife to view.
    From $956 per night (USD)

    Expedia

    Private Ranch home hidden in the woods with lots of wildlife to view.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Located on the edge of Plymouth, WI and a 1/2 mile to Hwy 23 for fast access to any major event in the area. Ranch home ...

    From $956 per night (USD)

    Expedia

    Details
  • 2 bed\/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
    From $279 per night (USD)

    VRBO

    2 bed\/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Modern/updated 2 bedroom 2 bath townhouse on a quite Cul-De-Sac in Sheboygan, WI. Every part of this house has been remo ...

    From $279 per night (USD)

    VRBO

    Details
  • Stay in style while attending the NFL draft pick at Greenbay’s Lambeau Field!
    From $1807 per night (USD)

    Expedia

    Stay in style while attending the NFL draft pick at Greenbay’s Lambeau Field!

    Bedrooms:
    9
    Bathrooms:
    10
    Sleeps:
    24

    The 10,000 square foot Castino Lakeview Mansion sits high atop a bluff with uninterrupted breathtaking views of Lake Mic ...

    From $1807 per night (USD)

    Expedia

    Details
  • Adorable 3 bedroom home in historic Sheboygan Falls
    From $151 per night (USD)

    VRBO

    Adorable 3 bedroom home in historic Sheboygan Falls

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Cute bungalow located on a quiet cul-de-sac with a relaxing pond and a large fenced in yard. Centrally located within 2 ...

    From $151 per night (USD)

    VRBO

    Details
  • Lake home with crystal clear water
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    Expedia

    Lake home with crystal clear water

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Come enjoy the pristine waters of Crystal Lake. Relax: Sip coffee or cocktails on our two large decks with sweeping lake ...

    Click For Pricing

    Expedia

    Details
  • Peace  & Calm Awaits You on Your Own Private Beach… it’s Your Happy Place
    From $1028 per night (USD)

    VRBO

    Peace & Calm Awaits You on Your Own Private Beach… it’s Your Happy Place

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to a mid century home with soaring ceilings directly on the sands of Lake Michigan. Your private beach front get ...

    From $1028 per night (USD)

    VRBO

    Details
  • Luxurious Newly Renovated 4 Bedroom Home Near Elkhart Lake, Green Bay & Kohler
    From $969 per night (USD)

    Expedia

    Luxurious Newly Renovated 4 Bedroom Home Near Elkhart Lake, Green Bay & Kohler

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    14

    Our beautiful, newly renovated home is your ultimate getaway retreat. This spacious house not only includes modern touc ...

    From $969 per night (USD)

    Expedia

    Details
  • Welcome to the \Lake Cottage\  where lake Michigan waves are calling
    From $369 per night (USD)

    VRBO

    Welcome to the \"Lake Cottage\" where lake Michigan waves are calling

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Make memories of a lifetime at the “Lake Cottage” On a private gravel road right on the Lake 1.5 hours north of Chicago, ...

    From $369 per night (USD)

    VRBO

    Details
  • 4 Bedroom Beachfront Condo - Fantastic Lake View
    From $542 per night (USD)

    Expedia

    4 Bedroom Beachfront Condo - Fantastic Lake View

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Clean & updated condo/villa at Blue Harbor condominiums. This gorgeous upper two story has 2 bedrooms, full bathroom, li ...

    From $542 per night (USD)

    Expedia

    Details
  • BeachDaze a Lake Michigan Property
    From $345 per night (USD)

    VRBO

    BeachDaze a Lake Michigan Property

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Everyday is a good day when your at Beachdaze! Bring your beach toys and make ALL the memories with family and friends ...

    From $345 per night (USD)

    VRBO

    Details
  • Rare Find! Huge Beach & Luxe Woodsy Cabin
    From $503 per night (USD)

    Expedia

    Rare Find! Huge Beach & Luxe Woodsy Cabin

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Enjoy a memorable escape on the beach AND in the woods at your private luxury cabin on Lake Michigan's beachfront. Feels ...

    From $503 per night (USD)

    Expedia

    Details
  • Cascade Lakefront Home: Boat Dock, Fire Pit!
    From $289 per night (USD)

    VRBO

    Cascade Lakefront Home: Boat Dock, Fire Pit!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Prepare for your ultimate lakeside retreat at this newly renovated Cascade lakefront property. Sitting right on Long Lak ...

    From $289 per night (USD)

    VRBO

    Details
  • NFL Draft Ready • Near Road America & Downtown • Modern Retreat • Hotel Quality
    From $1106 per night (USD)

    VRBO

    NFL Draft Ready • Near Road America & Downtown • Modern Retreat • Hotel Quality

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Attending the 2025 NFL Draft in Green Bay? This property is just one hour, door-to-door from downtown and offers transpo ...

    From $1106 per night (USD)

    VRBO

    Details
  • River Meadow Getaway in Sheboygan Falls
    From $969 per night (USD)

    VRBO

    River Meadow Getaway in Sheboygan Falls

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    Welcome! Whether for work, pleasure, or something in between, please come and enjoy our country setting with city conven ...

    From $969 per night (USD)

    VRBO

    Details
  • Lake Michigan Home with gorgeous views, great spot for family or golf retreat
    From $695 per night (USD)

    Expedia

    Lake Michigan Home with gorgeous views, great spot for family or golf retreat

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

    Our beautiful lakefront home is perfect for a relaxing retreat! Minutes to downtown Sheboygan, downtown Kohler with 5 ...

    From $695 per night (USD)

    Expedia

    Details
  • Experience Gracious Living & Destination Kohler
    From $1318 per night (USD)

    VRBO

    Experience Gracious Living & Destination Kohler

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Welcome! NEW spacious 4000ft² lodging centrally located: 5 World-Class golf courses, Road America, Elegant Wineries/Spas ...

    From $1318 per night (USD)

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  • NFL Draft Ready • Near Road America & Downtown • Entertainment Villa
    From $1028 per night (USD)

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    NFL Draft Ready • Near Road America & Downtown • Entertainment Villa

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    10

    Attending the 2025 NFL Draft in Green Bay? This property is just one hour, door-to-door, from downtown Green Bay and off ...

    From $1028 per night (USD)

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  • Country Cheese Factory - King Bed!
    From $208 per night (USD)

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    Country Cheese Factory - King Bed!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    See our other home and many reviews! https://airbnb.com/h/plymouth-guest-house Entire House! 4 minutes from Road Americ ...

    From $208 per night (USD)

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  • Wyatt's Country Home - King Bed!
    From $229 per night (USD)

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    Wyatt's Country Home - King Bed!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Soak up the modern vintage charm of our fully remodeled and updated home! Thank you for choosing our sparkling clean spa ...

    From $229 per night (USD)

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  • Beautiful, newly built 3rd floor Townhouse in historic Elkhart Lake, WI.
    From $441 per night (USD)

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    Beautiful, newly built 3rd floor Townhouse in historic Elkhart Lake, WI.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beautifully appointed, third floor Townhouse at the Trackside Townhouses across the road from famous Road America. Short ...

    From $441 per night (USD)

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  • Country Guest House
    From $258 per night (USD)

    Expedia

    Country Guest House

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    See our other listing! https://airbnb.com/h/cheese-factory-bnb Entire house! Cozy Warm! This beautiful and unique guest ...

    From $258 per night (USD)

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  • Country beauty on 5 acres
    From $258 per night (USD)

    VRBO

    Country beauty on 5 acres

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Single family home with 3 bedrooms, 3 bathrooms,1 with whirlpool tub and the other 2 have showers.Great room with 22 ft ...

    From $258 per night (USD)

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  • Private, 4-bedroom, 2.5-bath near Kohler golf & walking distance to winery!
    From $1879 per night (USD)

    VRBO

    Private, 4-bedroom, 2.5-bath near Kohler golf & walking distance to winery!

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    10

    Located on a dead-end street, this 4 bedroom home is less than 15 minutes away from Whistling Straits and many other gol ...

    From $1879 per night (USD)

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  • Large lakefront Cabin w\/ year-round activities & enough beds for everyone!
    From $672 per night (USD)

    VRBO

    Large lakefront Cabin w\/ year-round activities & enough beds for everyone!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    16

    Relax with the whole family at this peaceful lakefront cabin! Wake up to stunning views and days filled with kayaking, h ...

    From $672 per night (USD)

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  • RYDER CUP WISCONSIN LAKEFRONT HOUSE WITH ROOM FOR 12
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    Expedia

    RYDER CUP WISCONSIN LAKEFRONT HOUSE WITH ROOM FOR 12

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Amazing property with plenty of room, unlimited parking, and full use of a 240 Acre Fresh Water Spring Fed Lake right ou ...

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  • Beautiful Victorian Near Racing, Golfing, Hiking Etc...
    From $620 per night (USD)

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    Beautiful Victorian Near Racing, Golfing, Hiking Etc...

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    Make yourself comfortable in this large Victorian home! It has four spacious bedrooms with two full baths and is the ult ...

    From $620 per night (USD)

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  • Ryder Cup - Premier Location!
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    Expedia

    Ryder Cup - Premier Location!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This newly remodeled and professionally cleaned home is 8 minutes from Whistling Straits and within walking distance to ...

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  • Spacious Sheboygan Home w\/ Grill & Fire Pit!
    From $474 per night (USD)

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    Spacious Sheboygan Home w\/ Grill & Fire Pit!

    Bedrooms:
    3
    Bathrooms:
    7
    Sleeps:
    10

    Escape the mundane and discover Lake Michigan bliss at this 5-bedroom, 3-bathroom Sheboygan vacation rental! Start your ...

    From $474 per night (USD)

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  • RV Parking for NASCAR 2.5 Miles from Road America
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    RV Parking for NASCAR 2.5 Miles from Road America

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This space is for RV PARKING for NASCAR. All local campground and Road America are SOLD OUT. We are 2.5 miles from Road ...

    Click For Pricing

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    Details
  • Downtown Sheboygan Apartment w\/ Private Deck!
    From $241 per night (USD)

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    Downtown Sheboygan Apartment w\/ Private Deck!

    Bedrooms:
    1
    Bathrooms:
    5
    Sleeps:
    8

    Nestled in the heart of downtown, this 4-bedroom, 1-bathroom Sheboygan vacation rental is a walkable utopia for your nex ...

    From $241 per night (USD)

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  • Beautiful Home To Enjoy Your Experience
    From $1506 per night (USD)

    Expedia

    Beautiful Home To Enjoy Your Experience

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    11

    Beautiful home less than 5 miles from Elkhart Lake, 20 miles from Whistling Straights and 40 miles from the EAA Aviation ...

    From $1506 per night (USD)

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  • Elkhart Lake Townhome - 20 Mi to Sheboygan!
    From $368 per night (USD)

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    Elkhart Lake Townhome - 20 Mi to Sheboygan!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Make your escape to the 'Vulcan', a 1-bed, 1-bath vacation rental townhome less than a mile from the beaches of Elkhart ...

    From $368 per night (USD)

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  • Modern Townhome w\/ Deck - 1\/2 Mi to Elkhart Lake!
    From $466 per night (USD)

    Expedia

    Modern Townhome w\/ Deck - 1\/2 Mi to Elkhart Lake!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    Rev your engines at this 3-bed, 2-bath Elkhart Lake vacation rental! It’s no wonder the townhome carries the nickname 'R ...

    From $466 per night (USD)

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    Details
  • Elkhart Lake Townhome, Mins to Road America!
    From $449 per night (USD)

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    Elkhart Lake Townhome, Mins to Road America!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    Treat yourself to a worry-free retreat in Elkhart Lake - where life is good and living is easy! Make your vacation even ...

    From $449 per night (USD)

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  • Elkhart Lake Townhome - 3 Mi to Road America!
    From $404 per night (USD)

    Expedia

    Elkhart Lake Townhome - 3 Mi to Road America!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Consider this modern 2-bed, 2-bath vacation rental townhome your 'Vantage' point for exploring Elkhart Lake! This proper ...

    From $404 per night (USD)

    Expedia

    Details
  • Original Art |1904 Classic | Near Beach & Downtown
    From $392 per night (USD)

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    Original Art |1904 Classic | Near Beach & Downtown

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    7

    Newly renovated 1904 home in prime location. Remodeled kitchen and baths, gorgeous woodwork and floors, off-street parki ...

    From $392 per night (USD)

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  • Lillibridge Lake Home on Tittle Lake\/Long Lake All Season Fun
    From $223 per night (USD)

    Expedia

    Lillibridge Lake Home on Tittle Lake\/Long Lake All Season Fun

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    The Lillibridge Lake House is just steps from the water on quaint Tittle Lake, nestled in the Kettle Moraine State Fores ...

    From $223 per night (USD)

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  • Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
    From $158 per night (USD)

    VRBO

    Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Minutes east of I-43 nestled in beautiful wooded acreage with a short walk to the shores of Lake Michigan. This cottage ...

    From $158 per night (USD)

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  • Beach and Golf House
    From $402 per night (USD)

    Expedia

    Beach and Golf House

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    This home is in the perfect location to explore everything Sheboygan County has to offer. It is located in the historic ...

    From $402 per night (USD)

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  • BEST LAKE HOUSE, Lake Michigan, relaxing!
    From $429 per night (USD)

    VRBO

    BEST LAKE HOUSE, Lake Michigan, relaxing!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    A walkable beach is back as of 9-2024! Depending on the waves there is perhaps 2-6 feet of sand width and can walk north ...

    From $429 per night (USD)

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  • The Kohler House
    From $551 per night (USD)

    Expedia

    The Kohler House

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    The Kohler House is located in the quaint village of Kohler. Our family grew up in this neighborhood and created a spac ...

    From $551 per night (USD)

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    Details
  • REV your engines!!!!
    From $894 per night (USD)

    VRBO

    REV your engines!!!!

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    REV your engines. Located across from the Main Gate of the world famous National Park of Speed "Road America". This is ...

    From $894 per night (USD)

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  • Riverfront Victorian Downtown Sheboygan Falls
    From $125 per night (USD)

    Expedia

    Riverfront Victorian Downtown Sheboygan Falls

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Idyllic two story Victorian in downtown historic Sheboygan Falls on the Sheboygan River. With a short 5-10 min walk, one ...

    From $125 per night (USD)

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    Details
  • House, near Road America, Kohler, Lake Michigan
    From $397 per night (USD)

    VRBO

    House, near Road America, Kohler, Lake Michigan

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome! Warm spacious 3 bed/2 bath ranch home for rent. Our home is your home. Living room & Family Room. Master Bedro ...

    From $397 per night (USD)

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    Details
  • From Schwarz Supper Club to Road America, Schwarz Guest House is in Between.
    From $409 per night (USD)

    VRBO

    From Schwarz Supper Club to Road America, Schwarz Guest House is in Between.

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    The Schwarz family has been taking care of friends and customers for over 55 years. Dinner, drinks, and a good time is ...

    From $409 per night (USD)

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    Details
  • Summit Woods Hideaway! Walking Distance To Road America.  Elkhart Lake, WI 53020
    From $730 per night (USD)

    VRBO

    Summit Woods Hideaway! Walking Distance To Road America. Elkhart Lake, WI 53020

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Experience everything Road America and Elkhart Lake have to offer. This 2,500+ sqft home finished construction in Novem ...

    From $730 per night (USD)

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  • 2BR, 1.5BA, Pet-friendly, Lower duplex w\/finished basement + large backyard!
    From $141 per night (USD)

    VRBO

    2BR, 1.5BA, Pet-friendly, Lower duplex w\/finished basement + large backyard!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    This 2 bedroom, 2 bath lower duplex is the perfect spot to stay! It's just 3 short blocks to all of the restaurants of S ...

    From $141 per night (USD)

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  • Private Beach, Outdoor Dining, Firepit
    From $672 per night (USD)

    VRBO

    Private Beach, Outdoor Dining, Firepit

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Welcome to The Pond Cottage, hosted by Sheboygan Vacation Rentals! Beautifully updated and redecorated in 2025, our cot ...

    From $672 per night (USD)

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    Details
  • Classic brick charmer close to lake, river, and downtown!
    From $315 per night (USD)

    Expedia

    Classic brick charmer close to lake, river, and downtown!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Our classic 3 bedroom, 1 bathroom brick home located in the Historic Ellis District is central to the best experiences i ...

    From $315 per night (USD)

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  • Newly remodeled 3 bedroom ranch 10 minutes from Whistling Straits
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    Newly remodeled 3 bedroom ranch 10 minutes from Whistling Straits

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Newly remodeled 3 bedroom 2.5 bathrooms, located in quiet and safe, small town neighborhood. Minutes away from Sheboyg ...

    Click For Pricing

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  • 4 bedroom, 3 Bath Home only 9 Minutes from Road America
    From $765 per night (USD)

    VRBO

    4 bedroom, 3 Bath Home only 9 Minutes from Road America

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    Beautiful 4 bedroom, 3 bath home located on a quite dead end road only minutes from Road America, Kohler and PGA events ...

    From $765 per night (USD)

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  • Private home on twenty wooded acres.
    From $421 per night (USD)

    VRBO

    Private home on twenty wooded acres.

    Bedrooms:
    2
    Bathrooms:
    0
    Sleeps:
    0

    Located in the Northern Kettle Moraine Forest, this property is an hour north of Milwaukee and one hour and twenty minut ...

    From $421 per night (USD)

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    Details
  • Experience Lake Michigan views from your cozy 3-bedroom retreat
    From $502 per night (USD)

    Expedia

    Experience Lake Michigan views from your cozy 3-bedroom retreat

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Discover the beauty of a cozy three-bedroom holiday house located in picturesque Oostburg, mere footsteps from the breat ...

    From $502 per night (USD)

    Expedia

    Details
  • NEW Wooded Retreat on 3.5 Acres
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    NEW Wooded Retreat on 3.5 Acres

    Bedrooms:
    2
    Bathrooms:
    6
    Sleeps:
    14

    Unwind at this lodge style home, nestled on 3.5 acres of land, surrounded by trees. Secluded on a private road, the home ...

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  • The Long Lake Chalet
    From $370 per night (USD)

    VRBO

    The Long Lake Chalet

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    10

    This recently remodeled and tastefully furnished, PET FRIENDLY, cabin boasts a unique charm. Nestled along the shores of ...

    From $370 per night (USD)

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    Details