Holiday houses in Osceola

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.

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.

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.

Peaceful Lakeview Cabin Stay On Private Pennisula

Tucked on a private peninsula in Wisconsin’s Kettle Moraine, Birchwood Log Cabin is a quiet 4-bedroom, 2-bath retreat with stunning lake views and space for up to 14 guests. Enjoy a wraparound deck, wood-burning fireplace, and open-concept great room for cozy nights in. While our lake is view-only, you’re just a short walk to Kettle Moraine Lake’s public beach, boat launch, and vibrant Tiki Bar. Come for the stillness, stay for the trails, sunsets, and connection. Open year-round. Pets welcome!

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.

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!

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.

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!

hot tub and sauna on 5 private acres

Looking for a cozy winter retreat? Experience the Bird House, a tranquil Scandinavian-inspired private woodland paradise. Melt away stress in the hot tub and infrared sauna as you take in peaceful views of the meadow. Explore snowshoe and cross-country ski trails nearby in the scenic Kettle Moraine. Stream your favorite movie on the projector near the fireplace or unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee.

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.

GGG Spacious Log Cabin apartment on the IAT

With 10-11’ ceilings and 1000 sf, this sunny apartment is the second floor of an 1860’s log cabin. Completely updated with new floors, paint, fixtures and more, it’s a perfect retreat from the city. Explore the adjoining 500 acres of state forest, with public lake and boat launch across the street for fishing and paddling. The adjacent trail leads right the Parnell Segment of the Ice Age trail and Mauthe Lake State Park.

Private, Hot Tub, Sleeps 9, EV Charger

Enhance your well being with a relaxing getaway at The Pines located in the beautiful southern Kettle Moraine Forest area. Breathe in crisp fall air and take in the surrounding nature. Hike, forage, hunt, fish unplug for awhile. Near SoLu Winery, Parnell Tower and Road America. We are a wheelchair friendly property.