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.

Guest favorite

Cottage in Oostburg

4.97 out of 5 average rating, 229 reviews

Sandalwood 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.

Jan 8 – 15

$124 per night
Guest favorite

Home in Howards Grove

4.95 out of 5 average rating, 151 reviews

Spacious 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

$95 per night
Guest favorite

Cabin in Elkhart Lake

4.99 out of 5 average rating, 188 reviews

Elkhart 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

$213 per night

Popular amenities for Sheboygan County vacation rentals

Other great vacation rentals in Sheboygan County

Guest favorite

Apartment in Sheboygan

4.89 out of 5 average rating, 270 reviews

Spiritual Vibes Downtown Walk-up

Oct 19 – 26

$80 per night
Guest favorite

Home in Sheboygan

4.93 out of 5 average rating, 169 reviews

Beachfront getaway in Sheboygan

Dec 8 – 15

$206 per night
Guest favorite

Guest suite in Sheboygan

4.92 out of 5 average rating, 62 reviews

Cozy 1BD RM W/ fireplace by lake

Jun 11 – 18

$86 per night
Guest favorite

Townhouse in Sheboygan

4.94 out of 5 average rating, 80 reviews

Danz Sheboygan Retreat. Newly Remodeled in 2021.

Oct 16 – 23

$85 per night
Guest favorite

Apartment in Sheboygan

5.0 out of 5 average rating, 34 reviews

Quaint Blast from the Past - walk to lake/8th st

Apr 13 – 20

$107 per night
Guest favorite

Loft in Sheboygan

4.97 out of 5 average rating, 74 reviews

Spacious/stylish, 2br loft

May 8 – 15

$93 per night
Guest favorite

Apartment in Sheboygan

4.87 out of 5 average rating, 46 reviews

One Bdrm Apt - The Erie House near lake & downtown

Feb 6 – 13

$80 per night
Guest favorite

Cottage in Sheboygan

5.0 out of 5 average rating, 68 reviews

Cozy one bedroom cottage near lake Michigan!

Apr 16 – 23

$118 per night
Guest favorite

Guest suite in Waldo

4.92 out of 5 average rating, 37 reviews

Above Garage Apartment w/ Private Beach

Aug 6 – 13

$91 per night
Guest favorite

Home in Sheboygan

5.0 out of 5 average rating, 62 reviews

Relaxing Sheboygan/Kohler Getaway

Apr 27 – May 4

$104 per night
Guest favorite

Apartment in Sheboygan

5.0 out of 5 average rating, 85 reviews

Modern Upstairs Apt - Steps from Lake Michigan

Aug 24 – 31

$125 per night
Guest favorite

Apartment in Sheboygan

4.98 out of 5 average rating, 89 reviews

Lovely modern two bedroom home with fire pit

Feb 26 – Mar 5

$113 per night

Destinations to explore