Family-friendly vacation rentals in Winona

Penthouse Retreat-Near Downtown Winona!

Hi! This beautiful loft is conveniently located in the heart of Winona MN! Only a few blocks from the downtown and in close proximity to many other attractions Winona has to offer such as: Coffee, restaurants, a wine bar, Winona State University, Mississippi River, Lake Winona, hiking trails, Shakespeare Festival, Minnesota Marine Art Museum, and much more! Please allow us to make your next extended stay in beautiful Winona a memorable one! * MUST CLIMB STAIRS TO UNIT- LOCATED ON THE 3RD LEVEL

*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.

The Bungalow at the Healing Refuge

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

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.

Nostalgic Retro Cottage-Faye's Place-Fully Fenced

Welcome to Faye's Place! We are a 2 bedroom/1 bath Cottage on the Northside of La Crosse with a full fenced in yard! We are right off of 1-90. 2 Blocks from The Black River! Close to Kwik Trip, Walgreens, Food and Animal Watching! 10 min. away from downtown and UWL! Faye's Place is my childhood home and is a small immersive experience. Themed rooms, nostalgic items, games, toys and a treasure hunt! We decorate for all holidays. Ask about our Dive Bar Tour!

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.

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*

The Granary Guesthouse @ Harvest Home Farm

Harvest Home Farm is located at the end of a dead end road nestled in a valley, just 4 miles northeast of Whitehall, Wisconsin, in beautiful Trempealeau County. The 160 acre farm has a long term focus on raising grass fed sheep and poultry. We also have a produce garden, a berry patch, and an apple orchard. The farm has 80 acres of mixed hardwoods and softwoods and an abundance of wildlife as well as a network of walking trails.

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.

Potluck String Lodge (PSL)

Potluck String Lodge (PSL) is situated within Prairie Island Campground along 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 Boats and Bluegrass music festival and one of the campground picking circles hosted by the Potluck String Band.