Vacation rentals in Osceola
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Top-rated vacation rentals in Osceola
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
Cabin in Elkhart Lake
4.99 out of 5 average rating, 187 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
Cottage in Fond du Lac
4.97 out of 5 average rating, 230 reviewsCozy Guest House with Lake views.
Our remodeled two bedroom Guest House is adjacent to our Cottage and offers beautiful lake views. Access to Lake Winnebago available at near by boat launches. Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen bed and 2 twin beds, 1 full bathroom, and a fully stocked newly remodeled kitchen. Perfect getaway for some R&R with family or friends.
Sep 16 – 23
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Other great vacation rentals in Osceola
Townhouse in Port Washington
4.92 out of 5 average rating, 114 reviewsSteps Away From the Lakefront and Downtown
May 10 – 17
Cabin in Campbellsport
4.96 out of 5 average rating, 24 reviewsFraser Fir Rustic Cabin near Lake w/ Sunset Views
Sep 23 – 30
Apartment in Campbellsport
4.96 out of 5 average rating, 67 reviewsGGG Spacious Log Cabin apartment on the IAT
Apr 5 – 12
Cabin in Cascade
5.0 out of 5 average rating, 37 reviewsRustic Chic Cabin in Kettle Moraine
Apr 29 – May 6
Chalet in Campbellsport
4.96 out of 5 average rating, 83 reviewsLong Lake Chalet
Jun 5 – 12
Cabin in Cascade
5.0 out of 5 average rating, 30 reviewsmodern woodland paradise w/ sauna
Oct 22 – 29
Cottage in Campbellsport
4.88 out of 5 average rating, 58 reviewsPicturesque Lakeside Oasis on Kettle Moraine Lake
Jul 23 – 30
Apartment in Kewaskum
5.0 out of 5 average rating, 33 reviewsCozy Country Farmhouse
Nov 24 – Dec 1
Home in Waldo
4.98 out of 5 average rating, 57 reviewsPerfect Winter Getaway!
Sep 27 – Oct 4
Guest suite in Waldo
4.92 out of 5 average rating, 37 reviewsAbove Garage Apartment w/ Private Beach
Apr 23 – 30
Home in Fond du Lac
4.89 out of 5 average rating, 19 reviewsCute and Cozy Sleeps 6
Jul 2 – 9
Home in Cascade
5.0 out of 5 average rating, 46 reviewsThe Pines-Spacious Property, Private Home, Hot Tub
Sep 24 – Oct 1
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