Vacation rentals in Osceola

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Top-rated vacation rentals in Osceola

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Top guest favorite

The exterior of Norman's Place is shown, featuring a well-maintained farmhouse set against a backdrop of lush greenery. A garden bed with vibrant flowers is positioned near a prominent sign displaying the property's name. The spacious lawn leads up to the home, creating a welcoming entrance.

Home in Plymouth

4.99 out of 5 average rating, 70 reviews

Racers golfers outdoor lovers we're ready for YOU!

Norman's Place is a 1905 farmhouse nestled on the border of the Kettle Moraine State Forest in western Sheboygan County. The home includes 5 bedrooms, 2 full baths, full kitchen (with complimentary coffee, tea, 1 dz farm fresh eggs & 2 pizzas), laundry, traditional farmhouse dining & living rooms. Outdoor picnic area with charcoal grill & fire pit just feet from a glacial lake that has abundant wild life. The property is surrounded by natural beauty & farm fields. Perfect for a peaceful getaway.

Top guest favorite

Cabin in Elkhart Lake

4.99 out of 5 average rating, 297 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.

Top guest favorite

A person is seen holding a dark mug labeled 'The Coffee Corner Bistro Est. 1999' filled with a frothy beverage. The warm wooden interior of the café is visible in the background, enhancing the cozy atmosphere.

Apartment in Kewaskum

5 out of 5 average rating, 50 reviews

Local Landmark KL / Coffeehouse / Kettle Moraine

One-of-a-kind, newly renovated, turn-of-the-century Coffee Corner Suites, located at the "Gateway to the Kettle Moraine". Step out your door and into the iconic Coffee House. West Bend -- 5 minutes, Foundry 45 -- 3 minutes, Lomira -- 15 minutes. Rest easy knowing we have thought of everything to make your stay worry-free! King bed, full kitchen, keyless entry, heated towel bars, and on-site laundry. GOOGLE "Kewaskum is somewhere I just feel at home" and check out CBS 58 Story on Kewaskum.

Top guest favorite

The two-story home features a beige exterior with multiple windows, surrounded by a grassy yard. Two chairs are positioned in front on a small patio area. Large trees provide shade, while a view of the countryside and other structures is visible in the background.

Home in Glenbeulah

4.99 out of 5 average rating, 137 reviews

Stay at Sunrise LLC, Like being at Grandma's

Welcome to Stay at Sunrise LLC. We offer a clean and comfortable home for your vacation enjoyment. We are in a rural area, recreation trail head is 3 miles east of us as is the Wade House, 7 miles from Road America. Large yard, Fire pit, picnic table, child swing set. Garage parking on site if arranged in advance. We do not have WIFI Phone reception for Internet is good. No Cable or Satellite TV, Over 32 antenna channels. Smoking is allowed outside of the home. No pets allowed.

Top guest favorite

A charming log cabin features rustic wooden architecture, complemented by red window frames. Surrounded by lush greenery, the structure offers a welcoming front porch. Natural light bathes the exterior, enhancing the serene setting among the trees, with a pathway leading to the entrance.

Cabin in Campbellsport

4.96 out of 5 average rating, 95 reviews

Fraser Fir Rustic Cabin near Lake w/ Sunset Views

Take time to slow down in this timeless cabin on Kettle Moraine Lake. In the summer, enjoy quiet moments watching the sun set from the front porch, then relax by the fire pit under a sky full of stars. Fish from the dock, kayak around the lake, or bring your boat to soak up the sun. In the winter, grab your ice-skates or ice-fishing gear and head out on the lake. With countless trails nearby, the hiking options are limitless and beautiful in every season. Your next adventure awaits.

Guest favorite

A historic lighthouse stands at the water's edge, illuminated by the vibrant colors of sunset. Smooth stones line the shoreline, reflecting the serene lake. Lush greenery is visible in the background, creating a peaceful coastal setting.

Home in Fond du Lac

4.92 out of 5 average rating, 89 reviews

Woltring Waters Waterfront Home

Wake up to a beautiful view of Lake Winnebago, and enjoy you cup of coffee with the sound of crashing waves off the back porch. You will have breathtaking sunsets with the historical light house backdrop that is in viewing distance from the property. From dining to convenient stores everything you need is in walking distance. Take a peaceful stroll around the marina or take the kids to Lakeside Park, offering a petting zoo, carousel, train, jungle gym & splash pad. Everyone will enjoy!

Top guest favorite

A serene lakeside view features a setting sun casting warm hues over the water. A grassy area with neatly arranged seating faces the lake, while two trees provide a natural frame. Smooth stones and a pathway lead towards the water's edge.

Home in Fond du Lac

5 out of 5 average rating, 50 reviews

Spacious Lakefront 3Br 3Ba Home

Located directly on beautiful Lake Winnebago. Less than 15 minutes to Fond du Lac shops, bars, and restaurants. Conveniently only one hour from Milwaukee and Green Bay. Only 50 minutes to Whistling Straits, Kohler, and 30 minutes to Erin Hills! You'll enjoy a cozy three season room, a spacious patio with lots of seating, and large backyard with plenty of space for you and your family to enjoy! Nearby public golf courses include Whispering Springs, Rolling Meadows, and Far Vu Golf Course.

Top guest favorite

Cabin in Cascade

5 out of 5 average rating, 172 reviews

hot tub and sauna on 5 private acres

Need a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your inspired getaway awaits!

Top guest favorite

A remodeled kitchen and living area feature neutral tones and modern appliances. Bar stools are positioned at a counter, while a washer and dryer are present nearby. A dark brown armchair and a square ottoman are set on the soft carpet beside a small coffee table.

Cottage in Fond du Lac

4.98 out of 5 average rating, 284 reviews

Cozy 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.

Superhost

A modern bedroom features a king bed with neutral-colored linens and a decorative pillow. A bedside table with a lamp is placed next to the bed. The wall behind is adorned with wood paneling and a plant, adding a touch of nature to the space.

Apartment in Fond du Lac

5 out of 5 average rating, 16 reviews

Art District Loft 14 - Sleeps Five!

Welcome to the Art District Loft 14! Only 25 minutes to Road America, this modern loft has TWO KING beds and a comfy sofa to sleep five guests. Surrounded by local spots, you're steps away from downtown fun. Walk to bars, restaurants, and shops by foot! Enjoy the modern loft vibe and explore the town hassle-free. It's not just a stay; it's a laid-back and stylish suite for you and yours! *TOP ATTRACTIONS NEAR US* - EAA (18 mi) - Elkhart Lake (17 mi) - Road America (16 mi)

Top guest favorite

A historic stone building with arched windows is surrounded by well-maintained lawns and mature trees. A small shed is visible near the garden area, adding to the outdoor space's charm. Bright green grass and seasonal foliage contribute to the serene setting.

Home in Campbellsport

4.99 out of 5 average rating, 189 reviews

Gleason's Chouse

You'll love staying in our unique home, in a quiet neighborhood. This is a recently remodeled 1867 church converted to a "Chouse". Featuring 2 bedrooms, Full Kitchen, 1 Bathroom, Balcony, Parking, and a Gazebo.. all beautifully complimented by a range of antiques and decorations. 8 Miles East of Hwy 41, a 45 min drive to Oshkosh or an hour to Milwaukee. Just down the from Lake Bernice & Eisenbahn Bike Trail. Also close enough to the Kettle Moraine Forest to hike and sightsee!

Guest favorite

The cabin stands amidst lush greenery with a gently sloping lawn leading to a stone pathway. The modern exterior features large windows and a spacious upper deck surrounded by trees, providing a serene lakeside retreat.

Chalet in Campbellsport

4.97 out of 5 average rating, 106 reviews

Long Lake Chalet

This recently remodeled and tastefully furnished, PET FRIENDLY, cabin boasts a unique charm. Nestled along the shores of Long Lake in the heart of the Kettle Moraine Forest, this lakefront property offers 45’ of serene, peaceful beauty. This stunning home features a large yard, pier access and year round recreational activities. Disconnect, unwind and take in all that Kettle Moraine has to offer. Whether vacationing with family or friends this retreat is waiting for you.