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Results: 140 Rentals

  • Just 75 steps from the sand and shore of Lake Michigan!
    From $357 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 $357 per night (USD)

    VRBO

    Details
  • 3 Bedroom Beach House
    From $243 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 $243 per night (USD)

    Expedia

    Details
  • REMODELED HOME ON LAKE MICHIGAN
    From $212 per night (USD)

    VRBO

    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 $212 per night (USD)

    VRBO

    Details
  • Updated Sheboygan Home w\/ Porch < 1 Mi to Beach
    From $259 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 $259 per night (USD)

    Expedia

    Details
  • Family Home, 1 Block to Lake Michigan Beach!
    From $380 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 $380 per night (USD)

    VRBO

    Details
  • 2 bed\/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
    From $244 per night (USD)

    Expedia

    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 $244 per night (USD)

    Expedia

    Details
  • 4 Bedroom Beachfront Condo - Fantastic Lake View
    From $511 per night (USD)

    VRBO

    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 $511 per night (USD)

    VRBO

    Details
  • Ryder Cup - Premier Location!
    Click For Pricing

    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 ...

    Click For Pricing

    Expedia

    Details
  • Beach and Golf House
    From $376 per night (USD)

    VRBO

    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 $376 per night (USD)

    VRBO

    Details
  • Classic brick charmer close to lake, river, and downtown!
    From $308 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 $308 per night (USD)

    Expedia

    Details
  • Geele Ave Rental for Ryder Cup
    Click For Pricing

    VRBO

    Geele Ave Rental for Ryder Cup

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    5

    3 bedroom 2.5 bath home located near Lake Michigan and Downtown restaurants and shopping. Ready for the Women’s Golf Tou ...

    Click For Pricing

    VRBO

    Details
  • Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
    From $177 per night (USD)

    Expedia

    Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Kohler Design Center Rentals, Kohler Andrae State Park Rentals, Whistling Straits Rentals Blue Harbor Rentals, Road Amer ...

    From $177 per night (USD)

    Expedia

    Details
  • Edgewater Escapes. Steps to the beach - sleeps 10!
    From $709 per night (USD)

    VRBO

    Edgewater Escapes. Steps to the beach - sleeps 10!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Enjoy life on the shores of Lake Michigan in this luxury, courtyard condo. This two-story, 4 bedroom/3 bathroom get-awa ...

    From $709 per night (USD)

    VRBO

    Details
  • Edgewater Escapes - 4 bed condo steps to the lake
    From $714 per night (USD)

    Expedia

    Edgewater Escapes - 4 bed condo steps to the lake

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    14

    Enjoy life on the shores of Lake Michigan in this luxury, courtyard condo. This two-story, 4 bedroom/3 bathroom get-awa ...

    From $714 per night (USD)

    Expedia

    Details
  • A Wave from It All - King Suite - steps to the lake
    From $648 per night (USD)

    VRBO

    A Wave from It All - King Suite - steps to the lake

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Enjoy life on the shores of Lake Michigan in this king suite, courtyard condo. In close proximity to EVERYTHING, includ ...

    From $648 per night (USD)

    VRBO

    Details
  • Edgewater Escapes - 4 bed condo steps to the lake
    From $1006 per night (USD)

    Expedia

    Edgewater Escapes - 4 bed condo steps to the lake

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    14

    Enjoy life on the shores of Lake Michigan in this luxury, courtyard condo. This two-story, 4 bedroom/3 bathroom get-awa ...

    From $1006 per night (USD)

    Expedia

    Details
  • New 3 Bedroom property in the heart of downtown Sheboygan!
    From $347 per night (USD)

    VRBO

    New 3 Bedroom property in the heart of downtown Sheboygan!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Great family vacation home that sleeps 6 with 2.5 baths. Located next to the Weill Center for the Performing Arts and A ...

    From $347 per night (USD)

    VRBO

    Details
  • Updated Victorian in the Heart of Sheboygan. Beach, Downtown, Golf, Road America
    From $290 per night (USD)

    Expedia

    Updated Victorian in the Heart of Sheboygan. Beach, Downtown, Golf, Road America

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    9

    Lovingly restored 1890s Victorian home, updated to include the modern amenities you expect. Fully stocked kitchen, with ...

    From $290 per night (USD)

    Expedia

    Details
  • Cozy 2 bd home, minutes from lake Michigan
    From $279 per night (USD)

    VRBO

    Cozy 2 bd home, minutes from lake Michigan

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Cozy,Clean two bedroom home.Recently renovated. Fully equipped kitchen,fenced backyard for your pets.Walking distance to ...

    From $279 per night (USD)

    VRBO

    Details
  • Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan
    From $347 per night (USD)

    Expedia

    Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan

    Bedrooms:
    1
    Bathrooms:
    6
    Sleeps:
    10

    Whether you’re on the hunt for some good cheese, a delicious fried brat or just a simple lake retreat, this vacation ren ...

    From $347 per night (USD)

    Expedia

    Details
  • Fun family home near Ryder Cup
    Click For Pricing

    VRBO

    Fun family home near Ryder Cup

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Minutes from Ryder Cup, steps from Lake Michigan. 4 bedroom home with open concept family room, kitchen, and formal dini ...

    Click For Pricing

    VRBO

    Details
  • Central located. Seconds from the highway to get to kohler, and Elkhart lake
    From $811 per night (USD)

    Expedia

    Central located. Seconds from the highway to get to kohler, and Elkhart lake

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    14

    Everything you need on one level. complete modern Open concept living room, kitchen and dinning area. Hosts two large k ...

    From $811 per night (USD)

    Expedia

    Details
  • This location is13 minutes from 2020 Ryder cup at Whistling straights.  It's 2 blocks from the beach on lake Michigan.  We are only 3 blocks from numerous restaurants and local bars.
    Click For Pricing

    VRBO

    This location is13 minutes from 2020 Ryder cup at Whistling straights. It's 2 blocks from the beach on lake Michigan. We are only 3 blocks from numerous restaurants and local bars.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This house is warm and inviting. The fenced in backyard has a comfortable and covered patio area, with 2 propane fire p ...

    Click For Pricing

    VRBO

    Details
  • Ryder Cup 2021 - Home near Lake Michigan, 6 miles from Whistling Straits
    Click For Pricing

    Expedia

    Ryder Cup 2021 - Home near Lake Michigan, 6 miles from Whistling Straits

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    This mid-century modern home is situated in a quiet north Sheboygan Neighborhood, a 2 min walk to the Lake Michigan shor ...

    Click For Pricing

    Expedia

    Details
  • BEST LOCATION IN SHEBOYGAN!  Steps to beach & marina, walk to historic downtown!
    From $150 per night (USD)

    VRBO

    BEST LOCATION IN SHEBOYGAN! Steps to beach & marina, walk to historic downtown!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    My husband and I love to stay in a reasonably priced condo or flat when we travel. We like to feel like we are at a home ...

    From $150 per night (USD)

    VRBO

    Details
  • 10 min drive to Whistling Straits Golf course
    Click For Pricing

    Expedia

    10 min drive to Whistling Straits Golf course

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    4 bedroom House with 2.5 baths and finished basement. Lots of extra room to spread out or add air mattresses to accommod ...

    Click For Pricing

    Expedia

    Details
  • Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
    From $255 per night (USD)

    VRBO

    Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    7

    Escape to this spacious downtown riverfront retreat with easy access to nearby beaches, restaurants, and local shopping ...

    From $255 per night (USD)

    VRBO

    Details
  • Edgewater Escapes - 4 bed condo steps to the lake
    From $714 per night (USD)

    Expedia

    Edgewater Escapes - 4 bed condo steps to the lake

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    14

    Enjoy life on the shores of Lake Michigan in this luxury, courtyard condo. This two-story, 4 bedroom/3 bathroom get-awa ...

    From $714 per night (USD)

    Expedia

    Details
  • Beautiful Historic Home Near Lake Michigan
    Click For Pricing

    VRBO

    Beautiful Historic Home Near Lake Michigan

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    Beautiful historic home near Lake Michigan, only 6 blocks away. This house offers 4 bedrooms, 2 full bathrooms dinning ...

    Click For Pricing

    VRBO

    Details
  • Just Beachy - King Suite on Lake Michigan
    From $431 per night (USD)

    Expedia

    Just Beachy - King Suite on Lake Michigan

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Steps away from Lake Michigan, this 2 bed/2 bath has all you need! In close proximity to EVERYTHING, including the boar ...

    From $431 per night (USD)

    Expedia

    Details
  • Just Beachy - King Suite on Lake Michigan
    From $426 per night (USD)

    VRBO

    Just Beachy - King Suite on Lake Michigan

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Steps away from Lake Michigan, this 2 bed/2 bath has all you need! In close proximity to EVERYTHING, including the boar ...

    From $426 per night (USD)

    VRBO

    Details
  • BEACHVIEW GETAWAY
    From $392 per night (USD)

    Expedia

    BEACHVIEW GETAWAY

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    Amazing location just off of Lake Michigan. A quick walk to the public beach across the street or downtown as well. Prev ...

    From $392 per night (USD)

    Expedia

    Details
  • Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
    From $389 per night (USD)

    VRBO

    Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    11

    In this newly renovated landmark home you are walking distance from all that Sheboygan has to offer. Delicious food, nig ...

    From $389 per night (USD)

    VRBO

    Details
  • Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.
    From $764 per night (USD)

    Expedia

    Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Luxury Modern Farmhouse 4B-2Ba Lake & Beach House! Is it time for a Cool Change? Relax and rejuvenate at Sheboygan's n ...

    From $764 per night (USD)

    Expedia

    Details
  • Beachside, Chefs Kitchen, High-End Everything
    From $303 per night (USD)

    VRBO

    Beachside, Chefs Kitchen, High-End Everything

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to our "Delightful Seaside Picnic," hosted by Rose and Fern! This newly renovated home offers a serene retreat ...

    From $303 per night (USD)

    VRBO

    Details
  • Uniquely Designed, Near the Beach & all the Fun
    From $188 per night (USD)

    Expedia

    Uniquely Designed, Near the Beach & all the Fun

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to the Uptown Coach House. Our newly built coach house is nestled in the heart of downtown Sheboygan near all t ...

    From $188 per night (USD)

    Expedia

    Details
  • Charming 3-bedroom 3 Bathroom house in Sheboygan with AC, WiFi, & Amenities
    From $421 per night (USD)

    VRBO

    Charming 3-bedroom 3 Bathroom house in Sheboygan with AC, WiFi, & Amenities

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy a peaceful stay at this cozy 3-bedroom, 3 living room, and 3 bathroom home in Sheboygan, WI. This charming propert ...

    From $421 per night (USD)

    VRBO

    Details
  • Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
    From $153 per night (USD)

    Expedia

    Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    We welcome you to the historic district! Located 2 blocks from the famous Deland Park ( Malibu of the Midwest) and 2 bl ...

    From $153 per night (USD)

    Expedia

    Details
  • Luxury Beach Villa
    From $648 per night (USD)

    VRBO

    Luxury Beach Villa

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Two-story units are located on the 2nd and 3rd floors of the building with private entrance and balcony. Two bedrooms (s ...

    From $648 per night (USD)

    VRBO

    Details
  • Lake Shore Retreat: Sleeps 8!
    From $447 per night (USD)

    Expedia

    Lake Shore Retreat: Sleeps 8!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Enjoy a private entrance, with our two bedroom king suite. The master has a king size bed and an attached bathroom. The ...

    From $447 per night (USD)

    Expedia

    Details
  • Beachfront Villa - Sleeps 8.  Right on the beach!
    From $447 per night (USD)

    VRBO

    Beachfront Villa - Sleeps 8. Right on the beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Welcome to this charming villa in Sheboygan. This gorgeous property boasts 2 bedrooms, including a king bed, queen bed, ...

    From $447 per night (USD)

    VRBO

    Details
  • 2 Bedroom Beach Side Villa - Sleeps 8!
    From $700 per night (USD)

    Expedia

    2 Bedroom Beach Side Villa - Sleeps 8!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Steps away from Lake Michigan, this 2 bedroom/2 bath has all you need! In close proximity to EVERYTHING, including the b ...

    From $700 per night (USD)

    Expedia

    Details
  • Edgewater Escape steps from the beach! Sleeps 14!
    From $610 per night (USD)

    VRBO

    Edgewater Escape steps from the beach! Sleeps 14!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    14

    Enjoy life on the shores of Lake Michigan in this luxury, courtyard condo. This two-story, 4 bedroom/3 bathroom get-away ...

    From $610 per night (USD)

    VRBO

    Details
  • 2-bedroom villa in serene Sheboygan with WiFi, AC
    From $447 per night (USD)

    Expedia

    2-bedroom villa in serene Sheboygan with WiFi, AC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Nestled in Sheboygan right on the beach, this delightful villa is the perfect retreat for guests seeking a superb vacati ...

    From $447 per night (USD)

    Expedia

    Details
  • Unique 3-bedroom w\/easy access to Lake Michigan waterfront & downtown amenities
    From $427 per night (USD)

    VRBO

    Unique 3-bedroom w\/easy access to Lake Michigan waterfront & downtown amenities

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Welcome to Chateau Blu, a unique, beautifully appointed lakeview retreat. Nestled just a leisurely five-minute walk ...

    From $427 per night (USD)

    VRBO

    Details
  • 3 Bedroom lower unit -Brand New Remodel
    From $155 per night (USD)

    VRBO

    3 Bedroom lower unit -Brand New Remodel

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Complete Remodel just finished on this 3 BR 1 BA lower unit. New bathroom, kitchen, flooring, etc. in a central location ...

    From $155 per night (USD)

    VRBO

    Details
  • A Glorious Getaway Sheboygan - LUX Lake Condo
    From $447 per night (USD)

    VRBO

    A Glorious Getaway Sheboygan - LUX Lake Condo

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Summary: Welcome to a Glorious Getaway! Steps to Lake Michigan come and enjoy this luxury 4 bed 3 bath condo. Located i ...

    From $447 per night (USD)

    VRBO

    Details
  • 2BR Spacious Upper, Overlooking Kiwanis Park, Close to Everything!
    From $157 per night (USD)

    VRBO

    2BR Spacious Upper, Overlooking Kiwanis Park, Close to Everything!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    This an Upstairs Duplex with 2 bedrooms and 1 bath. Features a kitchen stocked with pots, pans, utensils, and kitchen ga ...

    From $157 per night (USD)

    VRBO

    Details
  • Dog-friendly centrally located townhouse on the Sheboygan River.\n
    Click For Pricing

    VRBO

    Dog-friendly centrally located townhouse on the Sheboygan River.\n

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Serene two-story, private entrance riverside condo located across the Sheboygan River from Der Sheboygan Biergarten. Les ...

    Click For Pricing

    VRBO

    Details
  • Scenic Lake Views in Sheboygan
    From $231 per night (USD)

    VRBO

    Scenic Lake Views in Sheboygan

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Watch the sun/moon come up over Lake Michigan across from the Sheboygan Marina and scenic lighthouse in this beautifully ...

    From $231 per night (USD)

    VRBO

    Details
  • 2BR Duplex Lower Overlooking Kiwanis Park
    From $149 per night (USD)

    VRBO

    2BR Duplex Lower Overlooking Kiwanis Park

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    This 2BR lower unit of a duplex is located in a quiet neighborhood, yet it is within walking distance of 2 coffee shops, ...

    From $149 per night (USD)

    VRBO

    Details
  • 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

    Details
  • The River Bed - Condo sleeps 4 on west side
    From $149 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 $149 per night (USD)

    VRBO

    Details
  • Lovely classic 2 blocks from Lake Michigan
    From $382 per night (USD)

    VRBO

    Lovely classic 2 blocks from Lake Michigan

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Newly renovated 1904 home in prime location. Brand new kitchen and baths, gorgeous woodwork and refinished wood floors, ...

    From $382 per night (USD)

    VRBO

    Details
  • Lake Michigan Home with gorgeous views, great spot for family or golf retreat
    From $593 per night (USD)

    VRBO

    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 $593 per night (USD)

    VRBO

    Details
  • Good Vibes on the Third Coast
    From $198 per night (USD)

    VRBO

    Good Vibes on the Third Coast

    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 $198 per night (USD)

    VRBO

    Details
  • Sheboygan Getaway w\/ Yard: 1 Mi to Lake Michigan
    From $355 per night (USD)

    VRBO

    Sheboygan Getaway w\/ Yard: 1 Mi to Lake Michigan

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Whether you're here to visit friends or family, this lower-level 2-bed, 1-bath Sheboygan vacation rental apartment has a ...

    From $355 per night (USD)

    VRBO

    Details
  • Malibu of the Midwest Condo steps from the Lake
    From $257 per night (USD)

    Expedia

    Malibu of the Midwest Condo steps from the Lake

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    7th Heaven Condo is in the popular South Pier district. Cute condo is on the 2nd floor with elevator access. Across the ...

    From $257 per night (USD)

    Expedia

    Details
  • Beach front luxury spacious villa !
    From $499 per night (USD)

    VRBO

    Beach front luxury spacious villa !

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Beach front luxury spacious condo! Beautiful remodeled four bedroom villa/condo overlooking Lake Michigan, well equippe ...

    From $499 per night (USD)

    VRBO

    Details
  • Riverfront Townhome with GIANT Rec Room and Private Riverfront Deck
    From $252 per night (USD)

    Expedia

    Riverfront Townhome with GIANT Rec Room and Private Riverfront Deck

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    More than just an inviting home away from home. It’s a friendly gesture, usually followed by a smile, and exchanged betw ...

    From $252 per night (USD)

    Expedia

    Details
  • 4 Bedroom Home on the River with Private River access
    From $236 per night (USD)

    VRBO

    4 Bedroom Home on the River with Private River access

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Take in the coastal vibes as you enjoy your stay at this Riverfront home. With private access to the river, kayaks to us ...

    From $236 per night (USD)

    VRBO

    Details
  • LUXE Manor with Modern, Elegant Vibes
    From $333 per night (USD)

    Expedia

    LUXE Manor with Modern, Elegant Vibes

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Modern chic blends with classic sophistication in this late 1800s Manor. Enjoy the expansive 4,500 square feet of elegan ...

    From $333 per night (USD)

    Expedia

    Details
  • Family-Friendly House: Walk to Lake Michigan!
    From $210 per night (USD)

    VRBO

    Family-Friendly House: Walk to Lake Michigan!

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    6

    Spend fun-filled days with your surfboard when you choose this conveniently located Sheboygan vacation rental! Just unde ...

    From $210 per night (USD)

    VRBO

    Details
  • Sleeps 7{SPACIOUS}Pets Welcome!
    From $296 per night (USD)

    Expedia

    Sleeps 7{SPACIOUS}Pets Welcome!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally ...

    From $296 per night (USD)

    Expedia

    Details
  • Huron Ave · Spacious & Peaceful Home in the heart of Sheboygan
    From $188 per night (USD)

    VRBO

    Huron Ave · Spacious & Peaceful Home in the heart of Sheboygan

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Come stay at a beautiful home close to Lake Michigan and downtown Sheboygan! Located in a quiet neighborhood, and two b ...

    From $188 per night (USD)

    VRBO

    Details
  • Newly remodeled private unit for 4+ week stays for up to 4 with pets, free w\/d
    From $116 per night (USD)

    Expedia

    Newly remodeled private unit for 4+ week stays for up to 4 with pets, free w\/d

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This amazing newly remodeled private first floor and private lower level of an upper/lower duplex is completely private ...

    From $116 per night (USD)

    Expedia

    Details
  • Beautiful Beachside Condo w\/ Stunning Lake Views
    From $166 per night (USD)

    VRBO

    Beautiful Beachside Condo w\/ Stunning Lake Views

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Blue water+White sand+Waves will surely make your stay in our second-floor condo a Wave of Happiness. Decide whether to ...

    From $166 per night (USD)

    VRBO

    Details
  • Dog-Friendly Sheboygan Home - 1 Mi to Town!
    From $129 per night (USD)

    Expedia

    Dog-Friendly Sheboygan Home - 1 Mi to Town!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Experience the best of Sheboygan with your loved one from this 1-bed, 1-bath vacation rental! This newly renovated home ...

    From $129 per night (USD)

    Expedia

    Details
  • Luxury Villa on Lake Michigan!
    From $728 per night (USD)

    VRBO

    Luxury Villa on Lake Michigan!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Summary: Welcome to the ideal place on Lake Michigan for a family beach getaway, wind surfing, fishing, bachelorette wee ...

    From $728 per night (USD)

    VRBO

    Details
  • 3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
    From $163 per night (USD)

    Expedia

    3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Forget your worries in this spacious and serene Guest House ( sleeps 4 people) queen bed and queen sofa bed. Minutes f ...

    From $163 per night (USD)

    Expedia

    Details
  • \n\nLuxury Downtown Sheboygan 4 Bdr 2 min walk to beach - Lakeside Legacy
    From $676 per night (USD)

    VRBO

    \n\nLuxury Downtown Sheboygan 4 Bdr 2 min walk to beach - Lakeside Legacy

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    Grand colonial meets coastal luxe in this 2800 square ft, 4 bedroom home along the magnificent Lake Michigan coast. Stun ...

    From $676 per night (USD)

    VRBO

    Details
  • Steps from Lake Michigan: North Point Place
    From $226 per night (USD)

    VRBO

    Steps from Lake Michigan: North Point Place

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Conveniently located for adventure and relaxation along the lakeshore and beyond, this historic home is steps away from ...

    From $226 per night (USD)

    VRBO

    Details
  • Cozy and private 3 bedroom unit located a few blocks from downtown Sheboygan.
    From $136 per night (USD)

    VRBO

    Cozy and private 3 bedroom unit located a few blocks from downtown Sheboygan.

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Located just a couple blocks from downtown Sheboygan! Visit the shops and unique restaurants just a short walk away, or ...

    From $136 per night (USD)

    VRBO

    Details
  • Amazing interior remodel for 7 in quiet safe walkable central neighborhood
    From $203 per night (USD)

    Expedia

    Amazing interior remodel for 7 in quiet safe walkable central neighborhood

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    This safe amazing newly remodeled interior is a 3-bedroom, 1 bath ranch home with driveway for parking. Large backyard, ...

    From $203 per night (USD)

    Expedia

    Details
  • Beach House on the shores of Lake Michigan Near downtown Sheboygan
    From $267 per night (USD)

    VRBO

    Beach House on the shores of Lake Michigan Near downtown Sheboygan

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Amazing location on the shores of Lake Michigan. One of only a few homes in the city of Sheboygan that are right on the ...

    From $267 per night (USD)

    VRBO

    Details
  • Logan Ave Holiday House - Upper
    From $314 per night (USD)

    Expedia

    Logan Ave Holiday House - Upper

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Unique attractions and endless days by Lake Michigan await at this ideally located vacation rental! Hosting 2 bedrooms, ...

    From $314 per night (USD)

    Expedia

    Details
  • COMFY, COZY, and CONVENIENT!!
    From $113 per night (USD)

    VRBO

    COMFY, COZY, and CONVENIENT!!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Whether you are here for golf, fishing, a Green Bay Packer game, Road America, or simply a vacation, this convenient She ...

    From $113 per night (USD)

    VRBO

    Details
  • Just Beachy - King Suite on Lake Michigan
    From $426 per night (USD)

    Expedia

    Just Beachy - King Suite on Lake Michigan

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Steps away from Lake Michigan, this 2 bed/2 bath has all you need! In close proximity to EVERYTHING, including the boar ...

    From $426 per night (USD)

    Expedia

    Details
  • *NEW* Sleeps 8 & Spacious!
    From $329 per night (USD)

    VRBO

    *NEW* Sleeps 8 & Spacious!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally ...

    From $329 per night (USD)

    VRBO

    Details
  • Riverfront Sheboygan Townhome w\/ Grill!
    From $228 per night (USD)

    Expedia

    Riverfront Sheboygan Townhome w\/ Grill!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Find rest and relaxation where the Sheboygan River flows into Lake Michigan at this 2-bedroom, 1.5-bathroom townhome. Th ...

    From $228 per night (USD)

    Expedia

    Details
  • Top Floor Condo With Lake Michigan Views Throughout!
    Click For Pricing

    VRBO

    Top Floor Condo With Lake Michigan Views Throughout!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Relax in this luxurious new construction condo! Enjoy top floor Lake Michigan Views from every room! Balcony with lots o ...

    Click For Pricing

    VRBO

    Details
  • Northside Charmer!
    Click For Pricing

    Expedia

    Northside Charmer!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Charming Northside Sheboygan home just 5 miles from Whistling Straits, a ten minute walk to Lake Michigan and 15 minute ...

    Click For Pricing

    Expedia

    Details
  •  5mi from the Ryder Cup @ Whistling Straits, natural beauty and serenity awaits!
    Click For Pricing

    VRBO

    5mi from the Ryder Cup @ Whistling Straits, natural beauty and serenity awaits!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Sleeping 8, this ranch home located just 6 miles as the crow flies from Whistling Straits golf course, offers a relaxing ...

    Click For Pricing

    VRBO

    Details
  • 'Beautiful Day Getaway' - Lake Michigan Views
    From $619 per night (USD)

    Expedia

    'Beautiful Day Getaway' - Lake Michigan Views

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Set your sights on the coastal community of Sheboygan, where you can find 2 miles of sandy beaches, epic sailing, and a ...

    From $619 per night (USD)

    Expedia

    Details
  • Shore House - 4 bed lakefront condo
    From $1102 per night (USD)

    VRBO

    Shore House - 4 bed lakefront condo

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    14

    Take in the views of Lake Michigan in your own private villa. This two-story, 4 bedroom/3 bathroom get-away is in close ...

    From $1102 per night (USD)

    VRBO

    Details
  • GUEST HOUSE SHORT WALK TO LAKE MICHIGAN\/Close to Downtown  & S Pier\n4bdrm 2 bath
    From $401 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 $401 per night (USD)

    Expedia

    Details
  • 5 Bedroom Modern House
    From $433 per night (USD)

    VRBO

    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 $433 per night (USD)

    VRBO

    Details
  • Downtown Sheboygan Apartment w\/ Private Deck!
    From $212 per night (USD)

    Expedia

    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 $212 per night (USD)

    Expedia

    Details
  • Sheboygan Home w\/ Views of Lake & Lighthouse!
    From $603 per night (USD)

    VRBO

    Sheboygan Home w\/ Views of Lake & Lighthouse!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    6

    Privacy at its finest! Book a stay at this 4-bedroom, 3.5-bathroom vacation rental in Sheboygan for unparalleled relaxat ...

    From $603 per night (USD)

    VRBO

    Details
  • Apt w\/ Shared Gas Grill, 2 Blocks to Dtwn!
    Click For Pricing

    Expedia

    Apt w\/ Shared Gas Grill, 2 Blocks to Dtwn!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    Escape to Lake Michigan when you choose this centrally located Sheboygan vacation rental! Bring your fishing rods to spe ...

    Click For Pricing

    Expedia

    Details
  • Beautiful 3BR Home Near Lake MI
    From $558 per night (USD)

    VRBO

    Beautiful 3BR Home Near Lake MI

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Welcome to our beautiful 3 bedroom, 1 1/2 bathroom house in Sheboygan, Wisconsin, one block away from the stunning Lake ...

    From $558 per night (USD)

    VRBO

    Details
  • *NEW* Beautiful & Convenient!
    From $318 per night (USD)

    Expedia

    *NEW* Beautiful & Convenient!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally ...

    From $318 per night (USD)

    Expedia

    Details
  • Washington Ct · Serene Home One Block From Lake Michigan
    From $370 per night (USD)

    VRBO

    Washington Ct · Serene Home One Block From Lake Michigan

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Bring your loved ones to this spacious home a block from Lake Michigan and beautiful Deland Park! Located mere steps fro ...

    From $370 per night (USD)

    VRBO

    Details
  • Modern Coastal Retreat for 8: Brand New Remodel with Amazing Amenities!
    From $133 per night (USD)

    Expedia

    Modern Coastal Retreat for 8: Brand New Remodel with Amazing Amenities!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    This newly remodeled modern home with lower level TV lounge and dedicated office has a private fenced-in back patio with ...

    From $133 per night (USD)

    Expedia

    Details
  • Sheboygan Getaway w\/ Deck + On-Site Lake Access!
    From $272 per night (USD)

    VRBO

    Sheboygan Getaway w\/ Deck + On-Site Lake Access!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Plan for plenty of outdoor fun on your next Lake Michigan getaway when you stay at this Sheboygan vacation rental! With ...

    From $272 per night (USD)

    VRBO

    Details
  • Remodeled Cape Cod within steps of Lake Michigan
    Click For Pricing

    Expedia

    Remodeled Cape Cod within steps of Lake Michigan

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Our charming Cape Cod home is waiting for you! With 3 bedrooms, and 1.5 baths, we’re sure our home will meet the needs o ...

    Click For Pricing

    Expedia

    Details
  • Urban Lake Condo in Sheboygan's Historic Ellis District
    From $105 per night (USD)

    VRBO

    Urban Lake Condo in Sheboygan's Historic Ellis District

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Your family will be within walking distance of almost everything when you stay at this centrally-located harborside gem ...

    From $105 per night (USD)

    VRBO

    Details
  • The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
    From $363 per night (USD)

    Expedia

    The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Nestled in the heart of Sheboygan, our location is a true gem! We are just steps away from the shores of Lake Michigan a ...

    From $363 per night (USD)

    Expedia

    Details
  • Lovely Lake Lookout - Steps to Lake Michigan!
    From $234 per night (USD)

    VRBO

    Lovely Lake Lookout - Steps to Lake Michigan!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Welcome to Lovely Lake Lookout by Great Lakes Getaways! Experience pure bliss in this 2-bed, 2-bath condo near Lake Mic ...

    From $234 per night (USD)

    VRBO

    Details
  • Cute Quiet Neighborhood Hideway
    From $164 per night (USD)

    VRBO

    Cute Quiet Neighborhood Hideway

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Step back in time and relax in this 1930’s bungalow. Situated on the south side of the City of Sheboygan, able to feel t ...

    From $164 per night (USD)

    VRBO

    Details