Vacation rentals in Kewaskum

Waterfront Retreat *Gazebo*Private Deck*Fireplace

Imagine waking up to peaceful sounds of nature, stepping onto your private deck with a hot cup of coffee, & watching the morning light dance across the pond & gardens. Nestled on a charming 1880s homestead, our Waterfront Country Retreat offers 4 acres of beauty, walking paths, & wildlife. Relax by the indoor gas fireplace, enjoy the gazebo w/fireplace, or unwind in the tranquility of the countryside—just minutes from West Bend & a short drive to Cedarburg. Perfect for Romantics & Nature Lovers.

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 2nd floor that is equipped with a laundry room and full kitchen and bathroom. Sleeps 2-4 2. The NEUMANN SUITE is an efficiency apartment with a queen bed, efficiency refrigerator, right next door. Has bath with shower. Sleeps 1-2 Larger groups, I recommend using both. Each has own private entrance.

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.

Local Landmark CF / Artisan Coffeehouse

Wake up to the aroma of fresh coffee, stroll downstairs for breakfast, then spend the afternoon hiking the Kettle Moraine before returning to a luxurious bed. The iconic Coffee Corner Bistro (Est 1999) is steps from the Wisconsin 9/11 Memorial & Eisenbahn Bike Trail, and is the "Gateway to the Kettle Moraine" Proudly recognized by the Fond du Lac Reporter Travel Section in its June 13, 2026 feature: "Top Airbnb Stays Near Fond du Lac" Google CBS 58 story on our historical Coffeehouse.

Countryside Escape with a View

Forget your worries in this spacious and serene space displaying original works of art and maintaining a clean and minimalistic furnished atmosphere. This is a two-bedroom, one-bathroom, open-concept apartment, unique in the fact that it is attached to the resident’s home. The apartment offers a brand-new kitchen completely furnished for functionality and simplicity. It showcases gorgeous hand-crafted cabinetry, as well as an expansive window, providing a lovely view of the countryside.

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!

Kettle Trails Cottage on Long Lake

Kettle Trails Cottage is the perfect getaway to relax and have fun on the water. The 3 bed/1 bath home is a cozy, comfortable landing spot to unwind. The accompanying heated Boathouse is an ideal venue for entertainment, especially when the weather keeps you indoors. Bring family and friends for the fishing, hiking, kayaking, biking, hunting and horseback riding. This property is centrally-located on the western shore of Long Lake, with forest views and amazing sunrises guaranteed.

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!

Private 3 bedroom lake house

A beautiful spacious 3 bedroom with sofa bed (sleeps 9 guests) with lake access just steps away from the backyard. Includes washer and dryer, all cooking amenities and a grill, 3 TVs with cable (including Netflix and Disney+ capabilities), a two person canoe n 3 kayaks, hammock, board games, and books for leisure reading. Fish off the private peer. Light the bonfire in the fire pit (firewood included) by the patio onlooking the lake. Pets are allowed with a $200 pet fee.

Entire Use of Shalom House

Shalom House, a Frank Lloyd Wright style design, accommodates 1-12 guests with five bedrooms, 4 bathrooms, great room with fireplace, large kitchen, and labyrinth. NEW at Shalom House is WiFi, though the woods is a great place to connect with the world too. Wonderful drinking water and whole house water system. We have both!! *Shalom House is an experience-"a quiet place to be" *Enjoy the beauty of nature, friends, family, relaxation, celebration.

2 Bed/1 Bath Condo - West Bend

Experience West Bend, WI like a local in this 2-bedroom fully furnished condo. Step into this welcoming and adorable property- the kitchen in this unit is fully equipped with everything you need, including glassware, kitchen utensils, and pots and pans. Washer & Dryer is available within the unit. One garage spot and one exterior off-street parking spot is included in rental price. Our place is equipped for both long or short stays.