Family-friendly holiday rentals in Winona County

Country Cottage in SE MN Bluff Country near Winona

Experience the beauty SE MN & the Driftless Region. We are located in the beautiful and secluded Wiscoy Valley which straddles the boundaries of Rushford and Winona, MN. Surrounding area includes small towns, rolling valleys, sparkling creeks, and short drives to the Mississippi and Root rivers. Located 53 miles from Rochester, MN, 12 from Winona, MN, and 30 from LaCrosse, WI. *This is a very private N/S space with 3 stairs to access the first floor. Cell service varies but. v. good internet.

2nd Floor Retreat - 7 Blocks from WSU

Our one-bedroom apartment is perfect for two guests. * NO cleaning fee/deposit required * Spacious bedroom with queen size bed, couch and workspace * Fully kitchen with oven, refrigerator, microwave + coffee/tea station * TV, board games and books * All amenities needed for a comfortable stay * Walking distance to WSU and Cotter * Your own washer dryer in the apartment * Easy self-check-in process We want you to love your time in Winona and are here to make your stay as pleasant as possible.

Bright, spacious 3-bedroom farmhouse on 3 acres

Come stay in our recently updated 1800's farmhouse. Situated on 3 acres in a rural setting, this home is the perfect escape while still being centrally located among area attractions. Just 5 miles from the Mississippi, a state park and bike trail, a winery and an orchard, there is an abundance of nearby entertainment throughout the seasons. It is conveniently located between LaCrosse, WI and Winona, MN. WiFi and Roku available. There is ample off-street parking with space for trucks/trailers.

The Cottage at The Healing Refuge

Welcome to The Healing Refuge! Come experience life on a Minnesota farm nestled in the rolling hills of the Driftless area! Relax outside on the deck, swing in a hammock among the trees, or walk through our beautiful cover crop fields. This is a working farm & depending on the season, you are welcome to help collect eggs, chat with the horses, observe the numerous farm animals, or learn about regenerative farming. We want your experience at our farm to be relaxing and refreshing!

Quaint 1 bedroom cabin, with amazing views!

Peaceful 1 bedroom cabin overlooking views of the beautiful whitewater valley (35 minutes away from Rochester Minnesota). Perfect for a quiet, off-the-grid, retreat. - compost toilet -two burner stove -gas heater for the colder months -5 gallons of water included, more If needed Queen size bed beneath 3ft by 3ft skylight with stunning views of stars at night. 120 private acres connected on two sides by the (WMA). 1 + mile of personal private hiking trails with scenic views.

Small Town Vibes with Amazing River & Bluff Views

Enjoy gorgeous view of the Mississippi River, bluffs, and trains, entertain yourself with the live music (occasionally late) from neighboring establishments, stargaze on the deck, or revel in the passing trains. This apartment is the perfect place to get away and relax. Bring up your boat as you'll have parking available in the driveway too! NOTE: this is an upstairs apartment, but we promise you won't be disappointed and want to come back again and again. NON SMOKING. No pets.

Bluffside cottage with gorgeous views

Hill Street House is the quintessential river-town residence, located within walking distance of Fountain City's quaint downtown, legendary pubs, and riverfront, but just far enough from the highway and trains to still get a good night's sleep. Perched snuggly on the bluffside overlooking the Mississippi River, you'll see an ever-changing panorama of river boats, barges, and birds in flight against a backdrop of Minnesota bluffs in the distance and a jumble of rooftops below.

Northshore Studio on Lake Onalaska

Lakefront studio where retro and rustic charm meets modern convenience. Studio offers everything you need for a relaxing and enjoyable stay including a queen-sized bed, a living area with a Roku TV, a full kitchen and a bathroom with a step in shower. The lakefront screen porch provides the perfect spot to enjoy your morning coffee or unwind with a good book. Two sit on top kayaks are included. Bikes are available and hiking and biking trails are just across the street.

Winona, MN- Cozy 3 bdrm bungalow with river view

Our home/cabin is up along the bluffs allowing eagle eye views of the Mississippi River. A perfect quiet place to take everything in. There are three bedrooms intended for large families or group get-aways. Everything is at your fingertips from beaches, to hikes in the bluffs. It is 3 miles south of Winona. While you can see the river, there is easy access to public landing if you choose to bring a boat to partake in the various islands and water sports.

Lakefront Studio

Lakefront studio One bedroom studio on the edge of the Upper Mississippi Wildlife Refuge. Surrounded on one side by beautiful Lake Onalaska with prairie walking trails on the other. You will not find a closer view of Lake Onalaska. There are two public boat landings less than a mile away. Stay and experience all that "God's Country" has to offer. Now sleeps three: We’ve added a new folding cot to accommodate an extra guest. *No cleaning fees*

Beautiful Views of the Mississippi river

This spacious 6300 sf home sits on 18 wooded acres and overlooks the Mississippi and is ideal for large groups. We can accommodate up to 14 guests. 5 bedrooms with 10 total beds. 2 kings, 3 queens, 5 twins. There’s also a pull out couch and additional mattresses. Large, fully stocked kitchen. 2 refrigerators and 3 large living rooms. Coffee maker and coffee. We have one outdoor security camera. Sorry, No pets.

Tamarack Point Homestead

Tamarack Point Homestead is located between Arcadia, WI and Centerville, WI in the beautiful valley of Tamarack. This scenic 150 year old homestead has an outbuilding loft that allows you to enjoy the country lifestyle and experience the best that Trempealeau County has to offer. Certified to operate by the Trempealeau County Health Department.