Family-friendly holiday rentals in Winona

Stunning Views! - Bunker 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. Bunker 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. *Check out our six other one-of-a-kind retreats listed on Airbnb located in Mindoro, WI

*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.

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!!!

1 Bedroom with Extra Amenities, Quiet Neighborhood

Our light-filled one-bedroom apartment is the perfect home away from home in Winona. * Spacious bedroom with queen size bed * Hardwood floors throughout * Full kitchen with oven, refrigerator, microwave + coffee/tea station * Within walking distance of Winona State University and Cotter High School * Located on the ground floor with parking * 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.

Ellie’s Place

This historic Winona home has gone through a complete renovation to make your stay enjoyable. It is in close proximity to many of the attractions that make Winona special: hiking/biking trails, Winona State University, Mississippi River, coffee shops, restaurants, bars, Lake Winona, Saint Mary’s University, Minnesota Marine Art Museum, music festivals, the winter ice wall and so much more.

Spacious Retreat for 1-8 guests

Staying with us for work or pleasure, this tranquil home is sure to suit all your needs. It has been renovated with charm and comfort in mind. All the modern indoor amenities will make you feel at home. Outdoors, enjoy the fully fenced in yard for privacy. It is conveniently located near Winona’s outdoor recreation, shopping, hospital and more.

Warbler Lodge

Warbler Lodge is situated within Prairie Island Campground along the backwaters of the Mississippi River. With cottony sheets, coffee & towels, paddle sport equipment & bikes, and an outdoor fire ring, you can simply show-up, relax, reconnect, and recreate. This tiny house tells a story about the flora and fauna of the Prairie Island park area.

Burton House (Downtown Winona)

The Burton House is a recently renovated, cozy little home just a few blocks from downtown Winona, MN and the mighty Mississippi River. It is walking distance to several restaurants, bars and shops. It's the perfect launch pad for outdoor enthusiasts, with wonderful recreation opportunities in and around Winona.