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 $1195 per night (USD)
VRBO
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 $1195 per night (USD)
VRBO
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Expedia
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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Expedia
From $243 per night (USD)
VRBO
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)
VRBO
From $227 per night (USD)
Expedia
REMODELED HOME ON LAKE MICHIGAN
Bedrooms:
1
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 $227 per night (USD)
Expedia
From $951 per night (USD)
VRBO
Beautiful Country Home Near Popular Hot Spots!
Bedrooms:
3
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 $951 per night (USD)
VRBO
From $791 per night (USD)
VRBO
Lake Orchard Farm Cottage
Bedrooms:
3
Bathrooms:
4
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
From $261 per night (USD)
VRBO
Updated Sheboygan Home w/ Porch < 1 Mi to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
100
Discover contemporary comfort right beside Lake Michigan’s coast with a trip to this 3-bedroom, 2-bathroom Sheboygan vac ...
From $261 per night (USD)
VRBO
From $419 per night (USD)
VRBO
Family Home, 1 Block to Lake Michigan Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
- Game Room - Central Location - Recently Remodeled From Lake Michigan to downtown, there's something for everyone at t ...
From $419 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 $600 per night (USD)
Expedia
Walk to Road America! Lake House on Private Peninsula
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Located on Little Elkhart Lake walking distance to Road America. Private 450' of waterfront on a peninsula with undevelo ...
From $600 per night (USD)
Expedia
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VRBO
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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VRBO
From $789 per night (USD)
Expedia
Elm Park Farmhouse 4 Miles from Road America and 45 Minutes from Green Bay
Bedrooms:
2
Bathrooms:
5
Sleeps:
16
The house is located 4 miles from Road America and about 45 minutes from Green Bay and Milwaukee. Country charm is throu ...
From $789 per night (USD)
Expedia
From $783 per night (USD)
VRBO
Beautiful private home hidden in the woods. Can sleep 11 guests
Bedrooms:
1
Bathrooms:
2
Sleeps:
11
NEW FOR 2025 BRAND NEW 7 person hot tub added to a beautiful rebuilt front deck along with deck lighting to-make this a ...
From $783 per night (USD)
VRBO
From $222 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 $222 per night (USD)
Expedia
From $369 per night (USD)
VRBO
Oostburg,WI Beach front cottage on Lake Michigan
Bedrooms:
1
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 $369 per night (USD)
VRBO
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Expedia
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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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
From $648 per night (USD)
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 ...
From $648 per night (USD)
Expedia
From $1424 per night (USD)
VRBO
Shoreline Sanctuary - 4 Bedroom Beachfront Condo
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to your perfect getaway at Shoreline Sanctuary! This beautifully updated and meticulously maintained condo is a ...
From $1424 per night (USD)
VRBO
From $884 per night (USD)
Expedia
Luxurious Newly Renovated 4 Bedroom Home Near Elkhart Lake, Green Bay & Kohler
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Our beautiful, newly renovated home is your ultimate getaway retreat. This spacious house not only includes modern touc ...
From $884 per night (USD)
Expedia
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VRBO
Ryder Cup - Premier Location!
Bedrooms:
1
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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VRBO
From $2125 per night (USD)
VRBO
Beautiful Home To Enjoy Your Experience
Bedrooms:
3
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 $2125 per night (USD)
VRBO
From $414 per night (USD)
VRBO
Modern Townhome w/ Deck - 1/2 Mi to Elkhart Lake!
Bedrooms:
2
Bathrooms:
3
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 $414 per night (USD)
VRBO
From $407 per night (USD)
VRBO
Elkhart Lake Townhome, Mins to Road America!
Bedrooms:
2
Bathrooms:
3
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 $407 per night (USD)
VRBO
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VRBO
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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VRBO
From $143 per night (USD)
Expedia
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Bedrooms:
1
Bathrooms:
2
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 $143 per night (USD)
Expedia
From $402 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 $402 per night (USD)
VRBO
From $876 per night (USD)
Expedia
REV your engines!!!!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
REV your engines. Located across from the Main Gate of the world famous National Park of Speed "Road America". This is ...
From $876 per night (USD)
Expedia
From $315 per night (USD)
VRBO
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)
VRBO
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Expedia
Ryder Cup Rental
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newer built 2017 2600sq ft home with 3 full bedrooms along with another living space upstairs. 7 miles from whistling st ...
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Expedia
From $398 per night (USD)
VRBO
Bender Haus-Elkhart Lake Home- 3 Bedrooms- Close to Lake, Golf & Racing!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
3 bedroom home in the heart of Elkhart Lake! Perfect for your trip to Road America, PGA Tour, family reunion or summer ...
From $398 per night (USD)
VRBO
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Expedia
Modern Ranch Home, minutes from Whistling Straits/Kohler/Sheboygan
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
We look forward to welcoming your group to our home North West Side House - Only 4.5 miles from Whistling Straits and 1 ...
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Expedia
From $187 per night (USD)
VRBO
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Kohler Design Center Rentals, Kohler Andrae State Park Rentals, Whistling Straits Rentals Blue Harbor Rentals, Road Amer ...
From $187 per night (USD)
VRBO
From $932 per night (USD)
Expedia
New home on Crystal Lake.
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Lake home completed in 2020 on a 130 acre Crystal Lake which is at the top of the aquifer and therefore "crystal clear" ...
From $932 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Super clean amazing location downtown Elkhart Lake
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This is for the Upper Unit of the Duplex. Fresh and clean updated 3 bedroom!! One king bed, one queen & two twin beds sl ...
From $436 per night (USD)
VRBO
From $436 per night (USD)
Expedia
One Minute to Road America - Close to PGA Golfing
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy the activities at the Race track, and come back for relaxation. Plenty to do nearby as well. Osthoff Resort 6 min ...
From $436 per night (USD)
Expedia
From $1185 per night (USD)
VRBO
House Neighboring Road America and the Mullet River
Bedrooms:
2
Bathrooms:
4
Sleeps:
14
Modern farmhouse nestled on a dead end road a mile from Road America and about an hour from Lambeau Field for the 2025 N ...
From $1185 per night (USD)
VRBO
From $324 per night (USD)
Expedia
Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Located at the very end of a beautiful private road, the Sand Castle Beach House is nestled between beautiful Lake Michi ...
From $324 per night (USD)
Expedia
From $345 per night (USD)
VRBO
Perfect Rating DT Home! Walk to Beach, Eats and More! 5 Min. to Road America!
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Welcome to ElkHEART Escape! You and your family& friends will fall in love with our newly renovated, 4 bedroom/2 Full ba ...
From $345 per night (USD)
VRBO
From $308 per night (USD)
Expedia
Updated Victorian in the Heart of Sheboygan. Beach, Downtown, Golf, Road America
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Lovingly restored 1890s Victorian home, updated to include the modern amenities you expect. Fully stocked kitchen, with ...
From $308 per night (USD)
Expedia
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VRBO
Spacious 6 bedroom Ryder Cup Getaway
Bedrooms:
3
Bathrooms:
6
Sleeps:
11
Your premier destination for the 2021 Ryder Cup. In the heart of the action, you will be conveniently located only 6 mi ...
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VRBO
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Expedia
Ryder Cup 2021 - Home near Lake Michigan, 6 miles from Whistling Straits
Bedrooms:
2
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 ...
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Expedia
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
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Expedia
Ryder Cup Ready-Minutes away from Whistling Straits
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
<p>Located in a rural area, this welcoming vacation home lets you experience it all in Sheboygan Falls. You'll easily ma ...
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Expedia
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VRBO
10 min drive to Whistling Straits Golf course
Bedrooms:
2
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 ...
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VRBO
From $274 per night (USD)
Expedia
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Escape to this spacious downtown riverfront retreat with easy access to nearby beaches, restaurants, and local shopping ...
From $274 per night (USD)
Expedia
From $633 per night (USD)
VRBO
Remodeled lake house on Lake Michigan, near Kohler
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located just south of Sheboygan, right on Lake Michigan. Blue Dune cottage has 3 bedrooms (2 upstairs, 1 on main level) ...
From $633 per night (USD)
VRBO
From $349 per night (USD)
VRBO
Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan
Bedrooms:
1
Bathrooms:
4
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 $349 per night (USD)
VRBO
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VRBO
Large Family Home DNC/Ryder Cup
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
4300 sq ft home boasts upper/lower living area, upper kitchen, lower kitchenette, 5 bedrooms, 3 full bathrooms; currentl ...
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VRBO
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Expedia
Perfect location for a visit to Sheboygan County
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Ranch home with walkout lower level overlooking the woods. Enjoy the view from the windows, 3 seasons room, or the spaci ...
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Expedia
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VRBO
Fun family home near Ryder Cup
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Minutes from Ryder Cup, steps from Lake Michigan. 4 bedroom home with open concept family room, kitchen, and formal dini ...
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VRBO
From $832 per night (USD)
VRBO
Secluded Modern Beach Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Our beautiful lake house is tucked quietly away from the main road and is only steps from the beach. We designed our 3,5 ...
From $832 per night (USD)
VRBO
From $827 per night (USD)
VRBO
Central located. Seconds from the highway to get to kohler, and Elkhart lake
Bedrooms:
2
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 $827 per night (USD)
VRBO
From $288 per night (USD)
Expedia
Riverview Getaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Lower level of a beautiful, spacious riverfront house built in classic Frank Lloyd Wright style. Lovely views from both ...
From $288 per night (USD)
Expedia
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VRBO
Ryder Cup rental just minutes from Whistling Straits Golf Course
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A spacious, open concept ranch home that has three bedrooms, two and a half bathrooms, first floor laundry, and cable TV ...
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VRBO
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Expedia
2021 Ryder Cup Retreat
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Enjoy a cup of coffee or a drink on the two-tiered deck, sit around a bonfire roasting marshmallows or relax in the hot ...
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Expedia
From $195 per night (USD)
VRBO
Fall and Holiday Dates Available! Long stays welcome!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Two bedroom, 2 bath condominium includes a 2 car garage, laundry, and a 3 season room overlooking farm fields on the edg ...
From $195 per night (USD)
VRBO
From $198 per night (USD)
Expedia
BEACHSIDE GETAWAY IN SHEBOYGAN
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located just one lot in from the beautiful shores or Lake Michigan. This amazing location provides year round stunning v ...
From $198 per night (USD)
Expedia
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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 ...
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VRBO
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Expedia
Perfect location for Ryder Cup!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Tri-level home in a quiet neighborhood with modern updates and less than five miles from the Ryder Cup! Perfect backyard ...
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Expedia
From $404 per night (USD)
VRBO
BEACHVIEW GETAWAY
Bedrooms:
1
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 $404 per night (USD)
VRBO
From $620 per night (USD)
Expedia
Beach Access near Kohler-Andrae
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
***New Softub Resort 300 6-person Hot Tub will be available for Winter guest use October 31st thru May 17th!*** Wheth ...
From $620 per night (USD)
Expedia
From $426 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
Enjoy your Sheboygan getaway in this spacious 4-bedroom, 2-bath home just a 5-minute walk to the lake. Sleeps 11 and pac ...
From $426 per night (USD)
VRBO
From $552 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 $552 per night (USD)
Expedia
From $844 per night (USD)
VRBO
Family Home w/ Indoor Pool ~ 2 Mi to Elkhart Lake!
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
Endless family fun awaits at this pet-friendly, 5-bedroom, 4-bath vacation rental in Elkhart Lake, WI! This spacious hom ...
From $844 per night (USD)
VRBO
From $158 per night (USD)
Expedia
Downtown, Uniquely Designed, Near the Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to the Uptown Coach House, hosted by Sheboygan Vacation Rentals. Our newly built coach house is nestled in the ...
From $158 per night (USD)
Expedia
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VRBO
Apartment Centrally Located
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Only two laps from Road America, or 20 minutes from the beach, this secluded apartment complex is located on the peacefu ...
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VRBO
From $385 per night (USD)
Expedia
Edgewater Villa: 4 Bedroom, Sleeps 14!
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Modern 4BR Courtyard Condo – Steps from the Beach in the "Malibu of the Midwest" Escape to Sheboygan, WI—a hidden gem o ...
From $385 per night (USD)
Expedia
From $263 per night (USD)
VRBO
Beachfront Paradise: King Suite - Sleeps 8!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Soak in Lake Michigan views from this 2BR/2BA beachside condo, just steps from the boardwalk, harbor, shops, and restaur ...
From $263 per night (USD)
VRBO
From $588 per night (USD)
Expedia
Lakeside Cabin Retreat Relax at Private Lake House!
Bedrooms:
1
Bathrooms:
3
Sleeps:
11
Overview Immerse yourself in tranquility at Highlander Hideaway, a unique longhouse-style retreat nestled on 70+ acre pr ...
From $588 per night (USD)
Expedia
From $305 per night (USD)
VRBO
3 Mi to Road America: Spacious Elkhart Lake Home!
Bedrooms:
2
Bathrooms:
5
Sleeps:
13
Large Fenced Backyard | Walk to Shops & Restaurants | Gas Grill (Propane Provided) Experience all that Elkhart Lake has ...
From $305 per night (USD)
VRBO
From $528 per night (USD)
Expedia
Cozy Lakefront Escape: Perfect for Seasonal Getaways & Large Groups
Bedrooms:
1
Bathrooms:
5
Sleeps:
14
Nestled on the picturesque point of Random Lake, Wisconsin, our inviting and family-friendly lakehouse offers a perfect ...
From $528 per night (USD)
Expedia
From $218 per night (USD)
VRBO
Cozy Elkhart Lake Apartment: Walk to Town & Dining
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Experience tranquility and serenity in this 2-bedroom, 1-bath vacation rental in Elkhart Lake, Wisconsin. This apartment ...
From $218 per night (USD)
VRBO
From $653 per night (USD)
Expedia
Vacation Paradise: 4 Bedroom, 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 $653 per night (USD)
Expedia
From $834 per night (USD)
VRBO
5 min from Road America. Great yard and plenty of parking
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
This enchanting house in Elkhart Lake offers 5 bedrooms, including 1 king bed and 4 queen beds. With 2 bathrooms featuri ...
From $834 per night (USD)
VRBO
From $505 per night (USD)
Expedia
Lake House-Kayaks/Paddle Boards/Private Pier
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
🌅 Luxury Lakefront Living w/ Private Pier, Kayaks, & More on Crystal Lake Welcome to the Crystal Lake Beauty hosted by ...
From $505 per night (USD)
Expedia
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VRBO
Charming, Modern Riverfront 2-bedroom South Pier, Sheboygan Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stay comfortably in Sheboygan at this 2-bedroom condo. The space features 2 lovely queen beds, 2 bathrooms with showers, ...
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VRBO
From $385 per night (USD)
Expedia
Edgewater Escape: 4 Bedroom, Sleeps 14!
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
This two-story 4 bedroom/3 bathroom get-away is in close proximity to EVERYTHING, including the boardwalk, harbor and do ...
From $385 per night (USD)
Expedia
From $623 per night (USD)
VRBO
Just Beachy: 4 Bedroom, Sleeps 12!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Newly Renovated 4BR/3BA Upper-Level Condo – Walk to Boardwalk, Harbor & More! Welcome to your perfect home away from ho ...
From $623 per night (USD)
VRBO
From $496 per night (USD)
Expedia
4- Bedroom Retreat w/ Sauna, Game Room, Patio & Walk to Golf, Bars & Restaurants
Bedrooms:
2
Bathrooms:
4
Sleeps:
13
This newly renovated home offers the ultimate blend of comfort, fun, and convenience. Located in the heart of the city, ...
From $496 per night (USD)
Expedia
From $260 per night (USD)
VRBO
The Historic Downtown Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Located in Sheboygan Falls, this adorable apartment offers 2 cozy bedrooms with queen beds, a lovely bathroom with a bat ...
From $260 per night (USD)
VRBO
From $250 per night (USD)
VRBO
The Hillside Cottage- 2 min Walk to Road America!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The Hillside Cottage is the perfect location for anyone visiting Elkhart Lake, Road America, or the many different golf ...
From $250 per night (USD)
VRBO
From $131 per night (USD)
VRBO
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your cozy getaway awaits in Sheboygan at this beautiful upper unit duplex . This nice space features 1 bedroom with a co ...
From $131 per night (USD)
VRBO
From $541 per night (USD)
VRBO
Charming 3-bedroom house seconds to downtown Elkhart
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Your cozy getaway awaits in Elkhart Lake at this newly-renovated historic house. Unwind in 3 bedrooms including a spacio ...
From $541 per night (USD)
VRBO
From $142 per night (USD)
VRBO
Overlook Oasis - Lakeside Stay in Ellis District
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to Overlook Oasis by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through Ap ...
From $142 per night (USD)
VRBO
From $300 per night (USD)
VRBO
Pet-Friendly 3BR Retreat!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Relaxing 3-Bedroom Retreat Near Lake Michigan – Pet Friendly! Welcome to your perfect home base in Sheboygan! This spac ...
From $300 per night (USD)
VRBO
From $426 per night (USD)
VRBO
Luxury Villa on Lake Michigan!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to the ideal place on Lake Michigan for a family beach getaway, wind surfing, fishing, bachelorette weekend, gol ...
From $426 per night (USD)
VRBO
From $552 per night (USD)
Expedia
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 $552 per night (USD)
Expedia
From $268 per night (USD)
VRBO
Country Homestead next to the City, with Perfect Location for Road America HPDE
Bedrooms:
0
Bathrooms:
4
Sleeps:
8
Welcome to our large country homestead next to the city of Plymouth, just minutes from Road America and Elkhart Lake. J ...
From $268 per night (USD)
VRBO
From $220 per night (USD)
Expedia
DOWNTOWN Elkhart Lake—Modern Cottage—Upper Condo AVAILABLE FOR OFF SEASON RENTAL
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
AVAILABLE OCTOBER THROUGH MAY FOR OFF SEASON MONTH TO MONTH RENTAL Lake Street Retreat is the UPPER unit in an origina ...
From $220 per night (USD)
Expedia
Click For Pricing
VRBO
16 MIN FROM RYDERCUP Wooded Retreat
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
3000 sq ft ranch 16 minutes from the Ryder Cup, this lovely 4 bed/2 bath is nestled in a beautiful wooded neighborhood a ...
Click For Pricing
VRBO
From $267 per night (USD)
VRBO
Lake Michigan Sand Beach & Wooded Privacy
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Located just east of Oostburg, Wisconsin beach and lake front home is a place to enjoy the seasons of Lake Michigan. You ...
From $267 per night (USD)
VRBO
From $347 per night (USD)
VRBO
Secluded Sanctuary with Beach and Woods
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Cottage is a beautifully decorated French Country bungalow located on 7.5 acres of a privately owned compound. Mile ...
From $347 per night (USD)
VRBO
From $1643 per night (USD)
VRBO
Spectacular Lake Michigan house just steps to the water
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Aptly named, the Crayola House where Lake Michigan hugs the property and you can see the water from nearly every room in ...
From $1643 per night (USD)
VRBO
From $728 per night (USD)
VRBO
4BR Villa on 25 Acres – 10min to Road America Fire Pit & Chef’s Kitchen
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Private 25-acre 4BR villa just 10 minutes from Road America & Elkhart Lake. A peaceful retreat with fire pit, orchard tr ...
From $728 per night (USD)
VRBO
From $202 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 $202 per night (USD)
VRBO
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
From $262 per night (USD)
Expedia
30 Second Walk To Downtown
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Eloquent home that is a 30 second walk to downtown. This luxurious home has everything for your Elkhart Lake vacation. O ...
From $262 per night (USD)
Expedia
From $232 per night (USD)
VRBO
2BR Spacious Upper, Overlooking Kiwanis Park, Close to Everything!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This an Upstairs Duplex with 2 bedrooms and 1 bath. Features a kitchen stocked with pots, pans, utensils, and kitchen ga ...
From $232 per night (USD)
VRBO
From $294 per night (USD)
Expedia
Experience Lake Michigan views from your cozy 3-bedroom retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover the beauty of a cozy three-bedroom holiday house located in picturesque Oostburg, mere footsteps from the breat ...
From $294 per night (USD)
Expedia

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Results: 265 Rentals