Holiday rentals in Osceola

Local Landmark CF / Coffeehouse / Kettle Moraine

This one-of-a-kind suite is located above a local landmark. The iconic Coffee Corner Bistro est 1999, is steps from the Wisconsin 9/11 Memorial & Eisenbahn Bike Trail, and is considered the "Gateway to the Kettle Moraine". West Bend - 5 minutes, Foundry 45 - 3 minutes, Lomira - 15 minutes. Enjoy relaxing in this spacious, stylish upper flat in a beautiful turn-of-the-century building. Google... “Kewaskum is somewhere I just feel at home”... and check out CBS 58 story on our Coffeehouse.

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.

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!

Riverside House

Scenic banks of the Mullet River in Plymouth Wis. Imagine waking up to the sounds of the river, enjoying your morning coffee with picturesque water views, and spending your evenings unwinding in the tranquility of nature. Located directly across from the Plymouth dirt track, and 5 miles from the legendary Road America. This is the ideal basecamp for race weekends. Walkable downtown fun! Explore the distillery, resale shops, and many restaurants. Book your stay and get ready for adventure!

Updated Woodsy 1800s Cabin w/Lake Access- Sleeps 6

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.

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 king and queen 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.

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

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.

Clean 1bd/1bath close to everything!

Charming 1 bedroom 1 bath with private entrance and parking. Close to downtown, Shopping malls, Zoo, Hospital, Airport,Main freeways. Full kitchen with stove, microwave, coffee pot, dishes. Unit has tv and wifi. Coin operated laundry is accessible on premis. Why stay at a hotel when you can feel at home in this lovely unit.

Beautiful Luxury Condo Suite w/Large Deck

This suite is located near beautiful Elkhart Lake, WI and close to Road America. It is the mid-level of a luxury condo with its own private outside deck. The suite includes a wet bar featuring a mini refrigerator, a microwave oven and a coffee maker.