Family-friendly vacation rentals in Winona

Stunning Views! - Moss Hill @HighPointRetreats

Perched in the solitude of nature, our ridge top cabin offers a picturesque view at one of the top elevations in all La Crosse County. Cozy up to your loved ones, relax with friends, or find inspiration in this luxury cabin in the woods. Moss Hill cabin is named after Moss Hill Summit located ten miles southeast of the cabin. Moss Hill sleeps four and is non-smoking. Get your front row sunset seats on the private patio and relax by the fire. Immerse yourself in the tranquility and come stay us.

*Prairie Island Bungalow with Water Access*

Welcome to Prairie Island Bungalow (PIB)! Located on Prairie Island in Winona, this home provides the perfect, quiet getaway for work or play, and is your gateway to outdoor adventure in the Winona area. River access is available on our private dock next door! With thoughtful amenities including a fully-stocked kitchen (with coffee and tea!), plush linens, Smart TVs, games and books, a fire pit, snowshoes, and kayak and canoe rentals; we invite you to simply show up and enjoy your stay at PIB!

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.

Quiet Cottage in the Valley with Sauna

Nestled in the bluffs of Winona, Minnesota, The Driftless Retreat is a cottage in the valley just one mile from Saint Mary's University and a 10 minute drive to downtown Winona and the Mississippi River. The cottage features a private front and back entrance, large backyard, and woodburning fireplace. Our hope is that The Driftless Retreat is just that, a retreat away from the every day. We believe that every detail matters and take pride in making your time here relaxing and enjoyable.

~ Third Street Suites ~ #1

This beautiful 2nd story suite (accessed by stairs only) is conveniently located in the heart of downtown Winona MN on Third Street! Everything Winona and the downtown area has to offer is within close proximity. Examples include: Coffee shops, restaurants, cocktail lounges, bars, brewery, Winona State University, Mississippi River, Lake Winona, hiking Shakespeare Festival, Minnesota Marine Art Museum, & much more! Please allow us to make your next stay in beautiful Winona a memorable one!

River Road Abode: breathtaking river views

Entire 2 bedroom home with amazing views of the Mississippi from every room in the house. 3 unique decks to watch birds, barges, boats, bluffs and trains. Out front you can wave at people passing by on the Great River Road. Located near WI and MN state parks, wineries, breweries, and restaurants. Adventure outdoors or stay in and watch all the Mississippi has to offer from the private patio and decks. Trains pass by property day & night. Home is well insulated & ear plugs are provided.

Beautiful Views of the Mississippi river

Escape to a private Mississippi River retreat on 18 wooded acres. This spacious 6,300 sq ft home sits up high with stunning views of the river. It sleeps up to 14 with 5 bedrooms, 10 beds, and multiple living areas perfect for groups and gatherings. Enjoy a fully stocked kitchen with two fridges, complimentary coffee, laundry, a game room, games, and an outdoor fire pit. Peaceful, secluded, and designed for comfort—your ideal riverside getaway. No pets. Nearly 200 5-star reviews!!!

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.

Silo Loft Guesthouse

Our silo guesthouse provides a beautiful country retreat surrounded by hundreds of acres of woods and farm land. This working dairy farm is the perfect stay for a tranquil get away or the full dairy farm experience. If you’re looking for a CLEAN, peaceful & unique stay, this is the place for you! Recent guests say it’s the “hidden gem” of MN! Just 10-30 minutes from local coffee shops, restaurants, and many outdoor activities, this getaway has something for everyone!

2nd Floor Retreat - 7 Blocks from WSU

Our one-bedroom apartment is perfect for two guests. * 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.

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.