Search Vacation Homes in Sheboygan

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Browse Select Sheboygan Vacation Homes

Home Away from Home
Manitowoc, WI
Located in the heart of Manitowoc, this vacation home is within 6 mi (10 km) of Holy Family Memorial, Wisconsin Maritime Museum, and YMCA Beach. Rahr West Art ...
4.8/5 Exceptional! (6 reviews)
"A relaxing, safe, clean large alternative to the hotels. Very nice!"

Reviewed on Oct 7, 2021

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Home Away from Home
2021 Ryder Cup - Exceptional Location and Amenities.
This family-friendly Sheboygan Falls vacation home is within 3 mi (5 km) of The Bull at Pinehurst Farms Golf Course and Kohler Design Center. Old Plank Road ...
5/5 Exceptional! (1 review)
Ryder Cup
"The house was perfect for us and the owners were so friendly and helpful. We totally enjoyed our stay. Thank you!"

Reviewed on Oct 13, 2021

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2021 Ryder Cup - Exceptional Location and Amenities.
Directly on Lake Michigan! Last Minute Bookings Welcome!
This family-friendly Sheboygan vacation home is located on the waterfront, within 2 mi (3 km) of Lake Michigan, Blue Harbor Resort & Conference Center Water ...
4.8/5 Exceptional! (129 reviews)
lake house stay in Sheboygan. We had a great time. The house sits on Lake Michigan and has views.
"We had a great time staying at the Lake House. Mark is a great host and his beautiful house has everything you need to make your stay perfect. Centrally located it was a perfect home base for us."

Reviewed on Oct 21, 2021

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Directly on Lake Michigan! Last Minute Bookings Welcome!
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Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
The price is $270 per night from Oct 28 to Oct 28
Situated in Reedsville, this vacation home is within 20 mi (32 km) of Lincoln Park Zoo, Wisconsin Maritime Museum, and Hickory Hills Country Club. Chilton Speedway ...
4.7/5 Exceptional! (7 reviews)
Great place
"Very nice, check in was easy and would definitely stay again"

Reviewed on Sep 29, 2021

Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
Offering ski-in/ski-out access, this resort in Fond du Lac is in the mountains, 2.9 mi (4.6 km) from Lake Winnebago, and close to winter activities such as cross-country ...
5/5 Exceptional! (1 review)
Amazing Family Get Together!
"Our large family had a magical Christmas! Our beautifully decorated rented home had everything we needed . We were all very comfortable during the day and night time sleeping . We had private spaces and family get together areas ."

Reviewed on Dec 30, 2019

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Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
Gleason's Chouse
Campbellsport, WI
The price is $130 per night from Oct 28 to Oct 28
Situated in Campbellsport, this historic vacation home is within 9 mi (15 km) of Campbellsport Drumlin State Park, Kettle Moraine State Forest, and The Golf ...
5/5 Exceptional! (7 reviews)
Delightful Getaway
"Fabulous find. This re-envisioned church is a gem. Beautiful, relaxing, and comfortable, this fabulous property was the perfect getaway spot for a lovely fall weekend in Wisconsin. We plan to return soon!"

Reviewed on Oct 6, 2021

Gleason's Chouse
Amazing location next to Ryder Cup!
Situated in Cleveland, this golf vacation home is 1.6 mi (2.6 km) from Lake Michigan and 2.4 mi (3.9 km) from Whistling Straits Golf Course. Fischer Creek State ...
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Amazing location next to Ryder Cup!
Ryder Cup Rental
Sheboygan Falls, WI
Situated in Sheboygan Falls, this vacation home is 2.9 mi (4.7 km) from Kohler Design Center and within 6 mi (10 km) of The Waelderhaus and HSHS St. Nicholas ...
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Ryder Cup Rental
Riverview near Kohler,  Road America and Lake
This family-friendly Sheboygan Falls vacation home is located on a river, within 3 mi (5 km) of The Bull at Pinehurst Farms Golf Course, Kohler Design Center ...
5/5 Exceptional! (6 reviews)
Very clean!
"Overall experience was very good. Exceptionally clean and well equipped. Enjoy the property very much."

Reviewed on Oct 4, 2021

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Riverview near Kohler, Road America and Lake
5 bedroom home minutes from Whistling Straits available for Ryder Cup rental
Situated in Cleveland, this vacation home is 2.4 mi (3.9 km) from Lake Michigan and within 9 mi (15 km) of Fischer Creek State Recreation Area and Whistling ...
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5 bedroom home minutes from Whistling Straits available for Ryder Cup rental
Newly Remodeled 2 Bed/2Bath Townhouse
Situated in Sheboygan, this vacation home is 2.1 mi (3.3 km) from Lake Michigan and 2.6 mi (4.3 km) from Aurora Clinic. University of Wisconsin-Sheboygan and ...
5/5 Exceptional! (90 reviews)
Relaxing getaway
"This property was everything I expected. We had a lovely relaxing extended weekend that allowed us to disconnect for a few days and recharge. Host was very responsive and pleasant to work with. I highly recommend and hope to return in the near future."

Reviewed on Sep 13, 2021

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Newly Remodeled 2 Bed/2Bath Townhouse
The Above Ryder Cup Retreat 4 Bedroom Home
3.5 out of 5
1105 Aspen Rd, Kohler, WI
Situated in Kohler, this golf vacation home is 1.2 mi (1.9 km) from Kohler Design Center and within 3 mi (5 km) of The Waelderhaus and Blackwolf Run. The Bull ...
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The Above Ryder Cup Retreat 4 Bedroom Home
Point Beach Guest House - Large, comfortable & quiet. Large yard. Near beach!
Located on a lake, this slopeside vacation home offers ski-in/ski-out access in Two Rivers within 2 mi (3 km) of Neshotah Beach and Lake Michigan and close to ...
5/5 Exceptional! (104 reviews)
Second stay and hope to be back again!
"Nice location and space! Right by Point Beach Park which is so fun. Hiked segments of the Ice Age Trail that are so close to the property!"

Reviewed on Oct 21, 2021

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Point Beach Guest House - Large, comfortable & quiet. Large yard. Near beach!
Welcome to the "Lake Cottage"  where lake Michigan waves are calling
Situated on the beach, this family-friendly vacation home is 0.1 mi (0.1 km) from Lake Michigan and within 3 mi (5 km) of Harrington Beach State Park and North ...
5/5 Exceptional! (46 reviews)
Cozy Cottage
"We loved how cozy the cottage was! Very clean! We loved being able to sit out by the lake and just enjoy the view! The hosts were fabulous and had everything we needed to grill out or just sit by the fire pit. We would love to return!"

Reviewed on Oct 16, 2021

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Welcome to the "Lake Cottage" where lake Michigan waves are calling
Ryder Cup rental just minutes from Whistling Straits Golf Course
Situated in Sheboygan, this vacation home is within 9 mi (15 km) of Whistling Straits Golf Course, Kohler Design Center, and HSHS St. Nicholas Hospital. Aurora ...
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Ryder Cup rental just minutes from Whistling Straits Golf Course
Oostburg, WI, Lake Front Cottage
This family-friendly Oostburg vacation home is located on the waterfront, 0.1 mi (0.1 km) from Lake Michigan, and within 12 mi (20 km) of Blue Harbor Resort ...
4.8/5 Exceptional! (25 reviews)
Great view!
"We had a nice time."

Reviewed on Oct 20, 2021

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Oostburg, WI, Lake Front Cottage
Inviting Townhome w/ Porch, Walk to Lake Elkhart!
Situated in Elkhart Lake, this vacation home is 2.9 mi (4.7 km) from Kettle Moraine State Forest and within 9 mi (15 km) of Road America and Old Plank Road Trailhead. ...
3.8/5 Good! (13 reviews)
Great place!
"Had a lovely time at the house…it was perfect for our weekend. Everything is in walking distance. Loved the downtown area, farmers market and all the lake activities on offer. Only complaint is the air conditioning upstairs was not very good…the vents just don’t let in the air flow well."

Reviewed on Sep 6, 2021

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Inviting Townhome w/ Porch, Walk to Lake Elkhart!
2021 Ryder Cup minutes away! Steps to Lake Michigan! Newly renovated flat!
Located in Ellis Historical District, this vacation home is within a 10-minute walk of John Michael Kohler Arts Center, North Side Municipal Beach, and Lake ...
4.9/5 Exceptional! (10 reviews)
Great location right on Lake Michigan
"Comfortable place. Not fancy but good kitchen plenty of room. You can walk along the lake. American club four miles away. Some great wineries in the area. One thing for owners no extra toilet paper"

Reviewed on Oct 22, 2021

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2021 Ryder Cup minutes away! Steps to Lake Michigan! Newly renovated flat!
Modern Townhome w/ Deck - ½ Mi to Elkhart Lake!
Located in Elkhart Lake, this family-friendly vacation home is 3 mi (4.8 km) from Kettle Moraine State Forest, and within 9 mi (15 km) of Sheboygan County Fairgrounds ...
5/5 Exceptional! (11 reviews)
A Winner
"The automobile theme and location is perfect for Elkhart Lake and racing enthusiasts like our family. The unit is spacious and clean. Restaurants and shops are in walking distance. Our unit was on the second floor and the balcony was great. The parking is convenient."

Reviewed on Oct 4, 2021

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Modern Townhome w/ Deck - ½ Mi to Elkhart Lake!
Bender Haus-Elkhart Lake Home- 3 Bedrooms- Close to  Lake, Golf & Racing!
Located in Elkhart Lake, this family-friendly vacation home is 3 mi (4.8 km) from Kettle Moraine State Forest, and within 9 mi (15 km) of Sheboygan County Fairgrounds ...
4.9/5 Exceptional! (34 reviews)
Excellent
"Clean and beautiful home. Super convenient location"

Reviewed on Aug 25, 2021

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Bender Haus-Elkhart Lake Home- 3 Bedrooms- Close to Lake, Golf & Racing!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Sheboygan

La Quinta Inn by Wyndham Sheboygan

La Quinta Inn by Wyndham Sheboygan

2.5 out of 5
2932 Kohler Memorial Dr, Sheboygan, WI
The price is $71 per night from Nov 2 to Nov 2
4/5 Very Good! (851 reviews)
"Proximity to where I had to go"

Reviewed on Oct 18, 2021

La Quinta Inn by Wyndham Sheboygan
AmericInn by Wyndham Sheboygan

AmericInn by Wyndham Sheboygan

2 out of 5
3664 S Taylor Dr, Sheboygan, WI
The price is $76 per night from Nov 3 to Nov 3
4.2/5 Excellent! (549 reviews)
"Clean, friendly staff, free breakfast."

Reviewed on Oct 17, 2021

AmericInn by Wyndham Sheboygan
Fairfield Inn & Suites by Marriott Sheboygan

Fairfield Inn & Suites by Marriott Sheboygan

2.5 out of 5
4117 South Taylor Drive, Sheboygan, WI
The price is $91 per night from Oct 31 to Oct 31
4.7/5 Exceptional! (87 reviews)
"Brand new facility- really well done!"

Reviewed on Oct 3, 2021

Fairfield Inn & Suites by Marriott Sheboygan
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Booking Tips to Find the Best Sheboygan Vacation Homes


How much does it cost to rent a vacation home in Sheboygan?

You can find incredible Sheboygan vacation homes for all types of budgets: between $71 and $270 per night. The more amenities the rental has, and its proximity to popular places, the higher the price.


What is the best time to stay in a vacation home in Sheboygan?

If you are looking for a great deal on your vacation home in Sheboygan, consider visiting in , when prices are usually cheaper.


How many vacation homes are available for rent in Sheboygan?

There are 152 rental houses to choose from for your trip. You’ll find holiday homes located throughout the city, near sightseeing spots, and close to local nature areas.


How do I find the best deal for a vacation home in Sheboygan?

Begin by entering your trip dates to see what type of Sheboygan rental houses are available. Use the map to zoom closer into the areas or zoom out to include more locations. Use the filters on the left side of your search results to narrow down by star rating, price, number of bedrooms, amenities, and more—Expedia makes it easy to score the best deal for your budget.


Why should I rent a vacation home in Sheboygan?

Booking Sheboygan vacation home rentals is the perfect way to spend a vacation because of the privacy, variety of amenities, and comfort you’ll have in your own space.


What amenities are available in a private vacation home?

When thinking about what you want in your Sheboygan rental house, dream big! Depending on your budget and the area, you’ll find amenities like a private pool, hot tub, free parking, fully-equipped kitchen, in-home washer and dryer, Wi-Fi, and a beautiful view or easy access to local sightseeing spots. You can even filter your search results by accessibility to ensure that everyone in your party will be comfortable.


Why should I book a vacation home with Expedia?

Expedia has some of the best selection and deals on available vacation homes in the area—and all in one place. We reward you with members points back on every booking and ensure you get the right accommodation for the best price. And you’ll save big when you bundle your travel together, like booking a car rental in Sheboygan along with your vacation property, into a Sheboygan vacation package.


Can I cancel my vacation home with Expedia?

Some accommodations are free to cancel and refundable if done so by a specific date, while others may be non-refundable. To make sure that you can get your money back on cancellations, use the “free cancellation” filter during your search. Contact our customer service portal if you need help.

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