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 $376 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 $376 per night (USD)
VRBO
From $1195 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 $1195 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 ...
Click For Pricing
VRBO
From $806 per night (USD)
VRBO
Elkhart Lake lakeside cottage
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 $806 per night (USD)
VRBO
From $341 per night (USD)
VRBO
260 Feet of Sandy Lake Michigan Beachfront
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Full on and private Lake Michigan water views abound at our historic family cottage, The Seagull Lodge. You’ll enjoy ex ...
From $341 per night (USD)
VRBO
From $225 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 $225 per night (USD)
Expedia
From $459 per night (USD)
VRBO
A GREAT PLACE ON A GREAT LAKE!
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 $459 per night (USD)
VRBO
From $384 per night (USD)
VRBO
Family Fun on Crystal Lake Island - minutes to Road America, hiking, PGA Golf
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
**2025 and 2026 calendar is open. Please note that our peak season rentals are a week minimum and run Monday-Monday** T ...
From $384 per night (USD)
VRBO
From $253 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 $253 per night (USD)
VRBO
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
From $227 per night (USD)
VRBO
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)
VRBO
From $951 per night (USD)
Expedia
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)
Expedia
From $435 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 $435 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
$Seagull Beach Guest House, Unique Lake Michigan Cottage\non private beach$
From $230 per night (USD)
VRBO
Seagull Beach Guest House, Unique Lake Michigan Cottage\non private beach
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 $230 per night (USD)
VRBO
From $163 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 $163 per night (USD)
VRBO
From $508 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 $508 per night (USD)
VRBO
From $428 per night (USD)
VRBO
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)
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 $403 per night (USD)
VRBO
Lake House - Great stay for Road America and Kohler golf
Bedrooms:
2
Bathrooms:
3
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 $403 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
From $1283 per night (USD)
VRBO
Quiet and spacious home, close to downtown, the beach, and fantastic golfing.
Bedrooms:
3
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
$Beach Lake House walking disance to lake Close to Downtown\n & South Pier\n4BR 2BA$
From $563 per night (USD)
Expedia
Beach Lake House walking disance to lake Close to Downtown\n & South Pier\n4BR 2BA
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 $563 per night (USD)
Expedia
From $390 per night (USD)
VRBO
A private, peaceful country home near Elkhart Lake
Bedrooms:
2
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 $390 per night (USD)
VRBO
From $252 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 $252 per night (USD)
VRBO
From $382 per night (USD)
VRBO
Beautiful Remodeled Lake Michigan Beachfront Home Country Setting w/ 500mbps int
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
NOW we have 5000mbps internet speed! Yes you can now work from (my)Home. Great large white sandy beach! Spacious rem ...
From $382 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 $296 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 $296 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 $600 per night (USD)
VRBO
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)
VRBO
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 $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 $844 per night (USD)
VRBO
Newly Remodeled Beachfront Home
Bedrooms:
3
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 $844 per night (USD)
VRBO
From $181 per night (USD)
VRBO
Good Vibes on the Third Coast-Pet Friendly! Cozy and Close by!
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Peaceful bohemian retreat filled with warmth and a lively vibe! Perfect for couples, remote workers, girls weekends, gol ...
From $181 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
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 $1986 per night (USD)
VRBO
Don’t be a turkey – Celebrate Thanksgiving with family all under one roof.
Bedrooms:
7
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 $1986 per night (USD)
VRBO
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)
VRBO
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)
VRBO
From $885 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 $885 per night (USD)
VRBO
From $884 per night (USD)
VRBO
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)
VRBO
$Welcome to the \Lake Cottage\ where lake Michigan waves are calling$
From $356 per night (USD)
Expedia
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 $356 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 $320 per night (USD)
Expedia
October Dates available!
Bedrooms:
1
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 $320 per night (USD)
Expedia
From $526 per night (USD)
VRBO
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 $526 per night (USD)
VRBO
From $969 per night (USD)
VRBO
River Meadow Getaway in Sheboygan Falls
Bedrooms:
3
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 $676 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 $676 per night (USD)
VRBO
From $1358 per night (USD)
VRBO
Experience Gracious Living & Destination Kohler
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome! NEW spacious 4000ft² lodging centrally located: 5 World-Class golf courses, Road America, Elegant Wineries/Spas ...
From $1358 per night (USD)
VRBO
From $168 per night (USD)
VRBO
Country Cheese Factory - King Bed!
Bedrooms:
1
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 $168 per night (USD)
VRBO
From $174 per night (USD)
Expedia
Wyatt's Country Home - King Bed!
Bedrooms:
1
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 $174 per night (USD)
Expedia
From $416 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 $416 per night (USD)
VRBO
From $154 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 $154 per night (USD)
Expedia
From $246 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 $246 per night (USD)
VRBO
From $1879 per night (USD)
VRBO
Private, 4-bedroom, 2.5-bath near Kohler golf & walking distance to winery!
Bedrooms:
3
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
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 ...
Click For Pricing
Expedia
From $610 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 $610 per night (USD)
VRBO
Click For Pricing
Expedia
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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Expedia
From $332 per night (USD)
VRBO
Spacious Sheboygan Home w/ Grill & Fire Pit!
Bedrooms:
3
Bathrooms:
5
Sleeps:
100
Escape the mundane and discover Lake Michigan bliss at this 5-bedroom, 3-bathroom Sheboygan vacation rental! Start your ...
From $332 per night (USD)
VRBO
From $334 per night (USD)
VRBO
Dtwn Sheboygan Apt Above Local Bar!
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Nestled in the heart of downtown, this 4-bedroom, 1-bathroom Sheboygan vacation rental is a walkable utopia for your nex ...
From $334 per night (USD)
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 $317 per night (USD)
VRBO
Elkhart Lake Townhome - 20 Mi to Sheboygan!
Bedrooms:
1
Bathrooms:
1
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 $317 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
From $383 per night (USD)
VRBO
Elkhart Lake Townhome - 3 Mi to Road America!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Consider this modern 2-bed, 2-bath vacation rental townhome your 'Vantage' point for exploring Elkhart Lake! This proper ...
From $383 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Art Collector’s Dream • Remodeled Masterpiece with Gallery Vibes
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Newly renovated 1904 home in prime location. Remodeled kitchen and baths, gorgeous woodwork and floors, off-street parki ...
From $347 per night (USD)
Expedia
From $190 per night (USD)
VRBO
Lillibridge Lake Home on Tittle Lake/Long Lake All Season Fun
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
The Lillibridge Lake House is just steps from the water on quaint Tittle Lake, nestled in the Kettle Moraine State Fores ...
From $190 per night (USD)
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 $425 per night (USD)
VRBO
BEST LAKE HOUSE, BEST BEACH HOUSE Lake Michigan, relaxing!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A walkable stunning white soft sand beach is back as of 2025! Depending on the waves there is perhaps 2-30 feet of sand ...
From $425 per night (USD)
VRBO
From $551 per night (USD)
VRBO
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)
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
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $399 per night (USD)
VRBO
House, near Road America, Kohler, Lake Michigan
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome! Warm spacious 3 bed/2 bath ranch home for rent. Our home is your home. Living room & Family Room. Master Bedro ...
From $399 per night (USD)
VRBO
From $348 per night (USD)
VRBO
From Schwarz Supper Club to Road America, Schwarz Guest House is in Between.
Bedrooms:
3
Bathrooms:
3
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 $348 per night (USD)
VRBO
From $796 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 $796 per night (USD)
VRBO
From $141 per night (USD)
VRBO
2BR, 1.5BA, Pet-friendly, Lower duplex w/finished basement + large backyard!
Bedrooms:
2
Bathrooms:
2
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 $574 per night (USD)
Expedia
Private Beach, Outdoor Dining, Firepit
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Welcome to The Pond Cottage, hosted by Sheboygan Vacation Rentals! Beautifully updated and redecorated in 2025, our cot ...
From $574 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
From $679 per night (USD)
VRBO
4 bedroom, 3 Bath Home only 9 Minutes from Road America
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Beautiful 4 bedroom, 3 bath home located on a quite dead end road only minutes from Road America, Kohler and PGA events ...
From $679 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 $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
From $362 per night (USD)
VRBO
Wander Back Inn to Elkhart Lake
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This gorgeous, new home is the perfect choice for your trip to Elkhart. Mere minutes away from famous local attractions ...
From $362 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $614 per night (USD)
VRBO
Stunning custom built country home with the ultimate game room!
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
The search is over, you have found the PERFECT retreat at Oaks Haven! Experience the tranquility of nature surrounded by ...
From $614 per night (USD)
VRBO
From $973 per night (USD)
VRBO
Whistling Straights 4 min, Blackwolf Run 7 min, Erin Hills 84 min, 3 Bedroom
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Two Story Home With 3 Bedrooms, 2-1/2 Bathrooms, Large Kitchen, Dinette, Formal Dining Room, Living Room, Family Room, ...
From $973 per night (USD)
VRBO
From $725 per night (USD)
VRBO
Road America Adjacent Lake House with indoor pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Road America adjacent four bedroom house on Little Elkhart Lake with indoor pool and spacious deck overlooking Little El ...
From $725 per night (USD)
VRBO
From $398 per night (USD)
Expedia
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)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $299 per night (USD)
Expedia
Fall dates available at SurfDaze!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful Cottage nestled on the WI shore of Lake Michigan. We have the best view of the water from inside the house an ...
From $299 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 $476 per night (USD)
VRBO
Heart of the Action, Village Square Upper Condo Sleeps 8
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Upper 4BR/2BA condo unit on the Village Park! Central location on Village Square across from historic train depot and re ...
From $476 per night (USD)
VRBO
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 $1036 per night (USD)
Expedia
6 Bedroom house on 7 acres
Bedrooms:
3
Bathrooms:
6
Sleeps:
18
6000 sq ft house on 7 acres within 20 minutes from Road America and all the areas popular golf courses including Whistli ...
From $1036 per night (USD)
Expedia
From $932 per night (USD)
VRBO
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)
VRBO
From $306 per night (USD)
VRBO
Wonderful 3+ Bedroom Home Completely Renovated
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Beautiful home in Sheboygan WI. Entire home has been completely remodeled and updated. Three entire floors of space fo ...
From $306 per night (USD)
VRBO

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