Sheboygan Area, Wisconsin Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Sheboygan Area, Wisconsin on RentalSaver.com!

Sheboygan Area Rentals

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
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
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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 ...
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VRBO
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
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)
VRBO
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)
VRBO
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
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
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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 ...
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VRBO
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
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
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)
VRBO
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)
VRBO
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
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
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
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
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
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
$Updated Sheboygan Home w\/ Porch < 1 Mi to Beach$
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
$Seagull Beach, Lake Michigan Cottage - Open for the NFL Draft 275\/night for 2-4$
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
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
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)
VRBO
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
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
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)
VRBO
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
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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 ...
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Expedia
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
$GUEST HOUSE SHORT WALK TO LAKE MICHIGAN\/Close to Downtown & S Pier\n4bdrm 2 bath$
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
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
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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 ...
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Expedia
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
$Beautiful Remodeled Lake Michigan Beachfront Home Country Setting w\/ 500mbps int$
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
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
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
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
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
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
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
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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 ...
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VRBO
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
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
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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 ...
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Expedia
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
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
$2 bed\/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub$
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
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
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
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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 ...
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Expedia
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
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
$Welcome to the \Lake Cottage\ where lake Michigan waves are calling$
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
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
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
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
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
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
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
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
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)
VRBO
From $1028 per night (USD)
VRBO
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)
VRBO
From $208 per night (USD)
VRBO
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)
VRBO
From $229 per night (USD)
Expedia
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)
Expedia
From $441 per night (USD)
VRBO
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)
VRBO
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)
Expedia
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)
VRBO
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)
VRBO
$Large lakefront Cabin w\/ year-round activities & enough beds for everyone!$
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)
VRBO
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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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Expedia
From $620 per night (USD)
VRBO
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)
VRBO
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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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Expedia
$Spacious Sheboygan Home w\/ Grill & Fire Pit!$
From $474 per night (USD)
VRBO
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)
VRBO
Click For Pricing
Expedia
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 ...
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Expedia
$Downtown Sheboygan Apartment w\/ Private Deck!$
From $241 per night (USD)
VRBO
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)
VRBO
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)
Expedia
From $368 per night (USD)
VRBO
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)
VRBO
$Modern Townhome w\/ Deck - 1\/2 Mi to Elkhart Lake!$
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)
Expedia
From $449 per night (USD)
VRBO
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)
VRBO
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
From $392 per night (USD)
VRBO
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)
VRBO
$Lillibridge Lake Home on Tittle Lake\/Long Lake All Season Fun$
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)
Expedia
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)
VRBO
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)
Expedia
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)
VRBO
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)
Expedia
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)
VRBO
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)
Expedia
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)
VRBO
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)
VRBO
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)
VRBO
$2BR, 1.5BA, Pet-friendly, Lower duplex w\/finished basement + large backyard!$
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)
VRBO
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)
VRBO
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)
Expedia
Click For Pricing
VRBO
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
VRBO
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)
VRBO
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)
VRBO
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
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
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)
VRBO

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