Holiday houses in Osceola

Shoreline Serenity

Welcome to ''Shoreline Serenity''! 200 ft of Lake Michigan frontage w/unobstructed views that go on for miles and tucked away on a 2-acre lot offering peace & privacy. Inside the home, you will be drawn to the beautiful views through the full wall of east facing windows & patio doors. The interior is cozy, clean, and comfortable. Fully equipped kitchen w/coffee bar. Main level has (2) bedrooms including the primary bedroom w/fantastic views. The spacious upper level loft has a king & twin bed.

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.

Wooded CABIN-Sunset & Lake Views/Kayak to Tiki Bar

Slow down at Fraser Fir log cabin, built in 1958 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.

Secluded Country Farm Getaway

Experience the best of both worlds at Bear Lake Ranch—where peaceful forest trails meet vibrant farm life, all in one unforgettable stay. Wander private hiking paths through Bear Lake and the Kettle Moraine State Forest, and enjoy the charm of a working farm. Just 15 minutes from Road America and Plymouth, 8 minutes to fishing and fun at Dundee’s Long Lake, 25 minutes to Kohler and Lake Michigan, and 45 minutes to EAA. Horse trailers, bikes, and boats are welcome. Relax, explore, and reconnect.

Peaceful Lakeview Cabin Stay On Private Peninsula

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!

Forest Lake Getaway

Get away from it all with a relaxing retreat on Forest Lake! This 4 bedroom/2 full bathroom lake home has space for 12 guests. A large open concept main floor and walk out lower level provide ample space to spread out and relax with family and friends in a beautiful forest setting with a private beach on Forest Lake. Enjoy year-round recreational activities at this four-season home! *UPGRADE* Issue identified! New water system is being installed early April to resolve the sulfuric water smell.

The Loft at Hickory Haven-A Modern Rural Studio

The Loft at Hickory Haven is a modern country retreat made for two! Mary & Bob constructed The Loft studio in 2020 and filled it with the modern traveler's amenity wish list: A comfy king bed, central AC, a gas-fired stove, a modern bathroom, and a kitchenette with dining area. The property's rural setting offers a peaceful haven from your daily grind. Your day will start with the chirping of birds or a wild turkey sighting and end with a star-filled sky that is a site to behold! Welcome!

Local Landmark CF / Coffeehouse / Kettle Moraine

One-of-three suites 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 somewhere I just feel at home” and check out CBS 58 story on our historic Coffeehouse

hot tub and sauna on 5 private acres

Looking for 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 getaway awaits!

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!

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.

The Cozy Country Farmhouse, Eisenbahn Suite

This 1865 COZY COUNRY FARMHOUSE is set only 1 mile out of Kewaskum. You get the best of both worlds county and a small town. There are 2 SUITES available. 1. The EISENBAUN SUITE is an apartment on the second floor that is equipped with a laundry room and full kitchen. Sleeps 4-6 2. The NEUMANN SUITE is an efficiency apartment on the second floor also with a queen bed, efficiency refrigerator right next door. Sleeps 2-3 For a larger group I recommend using both.