Vacation rentals in Sheboygan County
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Top-rated vacation rentals in Sheboygan County
Guests agree: these stays are highly rated for location, cleanliness, and more.
Cottage in Oostburg
4.97 out of 5 average rating, 229 reviewsSandalwood Cottage - 300 Feet From Lake Michigan
A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.
Dec 10 – 17
Home in Howards Grove
4.95 out of 5 average rating, 151 reviewsSpacious lower level priv entrance no cleaning fee
Entire basement is for rent with a separate entrance. Kitchen area includes refrigerator, microwave, coffee pot, toaster, sink, dining table and chairs. NO STOVE OR OVEN IS AVAILABLE. Free Wifi and Cable TV. Air conditioning. Plenty of parking, keyless entry. 14 min to Road America, 13 min to Kohler, 9 min to Whistling Straits, 5 min to Lakeland University, 1 hr to Milwaukee, 1 hr to Green Bay. Lots of nice amenities, clean, spacious. No cleaning fee. Unit NOT set up for babies or toddlers.
Dec 15 – 22
Cabin in Elkhart Lake
4.99 out of 5 average rating, 188 reviewsElkhart A-Frame, Wooded Retreat near Road America
The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.
Sep 12 – 19
Vacation rentals for every style
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Popular amenities for Sheboygan County vacation rentals
Other great vacation rentals in Sheboygan County
Guesthouse in Oostburg
4.9 out of 5 average rating, 253 reviewsBeach House
Oct 1 – 8
Apartment in Kohler
5.0 out of 5 average rating, 155 reviewsChurch Street Romance & Retreats-Village of Kohler
Nov 1 – 8
Guest suite in Sheboygan
4.92 out of 5 average rating, 62 reviewsCozy 1BD RM W/ fireplace by lake
Jun 10 – 17
Townhouse in Sheboygan
4.94 out of 5 average rating, 80 reviewsDanz Sheboygan Retreat. Newly Remodeled in 2021.
Oct 15 – 22
Apartment in Sheboygan
5.0 out of 5 average rating, 34 reviewsQuaint Blast from the Past - walk to lake/8th st
Apr 13 – 20
Home in Sheboygan
4.91 out of 5 average rating, 65 reviewsSpacious MCM Vibe Near Lake MI w/ Fire Pit
Dec 6 – 13
Guest suite in Waldo
4.92 out of 5 average rating, 37 reviewsAbove Garage Apartment w/ Private Beach
Apr 23 – 30
Apartment in Sheboygan
4.87 out of 5 average rating, 46 reviewsOne Bdrm Apt - The Erie House near lake & downtown
Apr 12 – 19
Cottage in Sheboygan
5.0 out of 5 average rating, 68 reviewsCozy one bedroom cottage near lake Michigan!
May 11 – 18
Apartment in Sheboygan
5.0 out of 5 average rating, 22 reviewsThe Sheboygan Foodie Flat
Apr 30 – May 7
Apartment in Sheboygan
5.0 out of 5 average rating, 85 reviewsModern Upstairs Apt - Steps from Lake Michigan
Oct 8 – 15
Home in Sheboygan Falls
4.98 out of 5 average rating, 53 reviewsAdorable bungalow in historic Sheboygan Falls,WI
Sep 7 – 14
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