Beginning of main content

Search over 1 million properties and 550 airlines worldwide

Members save 10% more on select hotels, cars, activities and vacation rentals. Sign up.

Free cancellation on most hotels. Because flexibility matters.


Vacation Rentals in Sheboygan

Estimated price for 1 night/2 adults

Grandstay Residential Suites Hotel - Sheboygan
Grandstay Residential Suites Hotel - Sheboygan
2.5 out of 5.0 708 Niagara Avenue, Sheboygan, WI
$134
4.3/5 (464 reviews)

No pool bc of covid 19 more information on the rooms

Reviewed on May 4, 2020
Located in Downtown, this aparthotel is within 1 mi (2 km) of Stefanie H. Weill Center for the Performing Arts and Blue Harbor Resort & Conference Center Water ...
Plymouth Rock Camping Resort
Plymouth Rock Camping Resort
2.0 out of 5.0 N7271 Lando Street, Plymouth, WI
3.7/5 (17 reviews)

Great place for campers RV'S cabins pools you can have camp fires I was empressed with the hot water how long it last in the cabins and we had 3 adults

Reviewed on Jun 3, 2019
Located in Plymouth, this family-friendly cabin is 0.9 mi (1.5 km) from Road America, and within 6 mi (10 km) of Sheboygan County Fairgrounds and Kettle Moraine ...
Directly on Lake Michigan! Last Minute Bookings Welcome!
Directly on Lake Michigan! Last Minute Bookings Welcome!
Sheboygan, WI
4.9/5 (120 reviews)

When even your teenage girls are awake every morning at 4:30 am to catch a sunrise, you know the location can’t be beat. We all had such a relaxing time and it was great to have the dog with us too!

Reviewed on Jun 28, 2020
Located in Downtown, this romantic vacation home is within 1 mi (2 km) of John Michael Kohler Arts Center and Blue Harbor Resort & Conference Center Water Park. ...
Rustic Retreat: Cabin and Deer Park Avoid the Crowds !
Rustic Retreat: Cabin and Deer Park Avoid the Crowds !
Elkhart Lake, WI
4.8/5 (6 reviews)

My son will forever remember his play time with the wolves and baby deer. We had so much fun feeding and visiting with the animals. The cabin had everything we needed and the hosts were super friendly. My son is already planning his stay for the next year.

Reviewed on Jul 2, 2020
Situated in Elkhart Lake, this cabin is 6.2 mi (10 km) from Wolf Lake and within 12 mi (20 km) of Road America and Ledge View Nature Center. Kettle Moraine State ...
Westward Ho RV Resort & Campground
Westward Ho RV Resort & Campground
3.0 out of 5.0 5456 North Division Road, Glenbeulah, WI
5.0/5 (2 reviews)

Better than expected due to late reservation during the Oshkosh AirVenture

Reviewed on Aug 23, 2017
Situated in Glenbeulah, this cabin is 4 mi (6.4 km) from Kettle Moraine State Forest and within 12 mi (20 km) of Road America and Wade House Historic Site. Wolf ...
Beautiful Victorian Near Racing, Golfing, Hiking Etc..
Beautiful Victorian Near Racing, Golfing, Hiking Etc..
Glenbeulah, WI
$300
4.9/5 (18 reviews)

We enjoyed our stay! The home is beautiful and very clean and the yard is gorgeous. The check in process was seamless. We highly recommend this property.

Reviewed on Jun 29, 2020
Situated in Glenbeulah, this vacation home is 0.4 mi (0.6 km) from Kettle Moraine State Forest and within 6 mi (10 km) of Road America and Wade House Historic ...
Executive Home Near Road America and 15 Minutes From Whistling Straights
Executive Home Near Road America and 15 Minutes From Whistling Straights
Plymouth, WI
$400
5.0/5 (1 reviews)

This property is really well kept and is in a nice and quiet neighborhood close to.many attractions in Sheboygan! Would definitely stay again!

Reviewed on Aug 8, 2019
Situated in Plymouth, this vacation home is within 3 mi (5 km) of Antoinette, Sheboygan County Fairgrounds, and Evergreen Golf Course. Kettle Moraine State Forest ...
Serene Peaceful Retreat With Many Recreational Activities "free Wifi"
Serene Peaceful Retreat With Many Recreational Activities "free Wifi"
Sheboygan, WI
4.7/5 (92 reviews)

This was a lovely experience! Great being right on the water next to some cute restaurants.

Reviewed on May 25, 2020
Located in the heart of Sheboygan, this romantic condo building is within 1 mi (2 km) of Lake Michigan and Blue Harbor Resort & Conference Center Water Park. ...
Point Beach Guest House - Large, Comfortable & Quiet. Large Yard. Near Beach!
Point Beach Guest House - Large, Comfortable & Quiet. Large Yard. Near Beach!
Two Rivers, WI
5.0/5 (83 reviews)

Stayed the weekend. The house was very cozy and had everything we needed and more! (wifi/kitchen/fireplace etc) Lots of beautiful nature around, outdoor space where you can relax (and see the stars at night!). Mike was helpful and friendly and happy to recommend things to do around.

Reviewed on Jun 29, 2020
Situated on a river, this vacation home is within 2 mi (3 km) of Neshotah Beach, Lake Michigan, and Point Beach State Forest. Neshotah Park and Rogers Street ...
Map

Frequently Asked Questions

Vacation Rentals in Sheboygan

Search for Vacation Rentals in Sheboygan on Expedia.com! You can easily find your home rentals, villas, short-term apartments for rent in Sheboygan using one of the methods below: 

  • View our selection of featured home rentals in Sheboygan
  • Use the map to find apartments and other vacation rentals in the Sheboygan neighbourhood you prefer
  • Enter your travel dates to view the best deals on vacation rentals in Sheboygan while they last

Look no further and take a look at our great range of rental properties in Sheboygan!

Other types of properties in Sheboygan you may be interested in

Estimated price for 1 night/2 adults

AmericInn by Wyndham Manitowoc

AmericInn by Wyndham Manitowoc

5020 Hecker Rd, Manitowoc, WI
  • Free Cancellation
  • Reserve now, pay when you stay
2.5 out of 5.0
 
 

AmericInn by Wyndham Manitowoc$85

Jul 7 - Jul 8

AmericInn by Wyndham Manitowoc$85
Lighthouse Inn

Lighthouse Inn

1515 Memorial Dr, Two Rivers, WI
  • Free Cancellation
  • Reserve now, pay when you stay
2.5 out of 5.0
 
 

Lighthouse Inn$101

Jul 7 - Jul 8

Lighthouse Inn$101