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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!

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!!!

The Guest House

Modern one-bedroom home— bright, fresh, and fully updated! This beautifully designed space seamlessly blends modern comfort with calming touches, making it perfect for relaxing after a long day of work, travel, or adventure. The home is just minutes from Winona’s lakes, trails, dining, and downtown attractions. Whether you’re here for outdoor adventure, a weekend getaway, or a comfortable remote-work base, this space offers everything you need for a smooth and enjoyable stay.

Bluffside cottage with gorgeous river 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.

Lady Liberty - bikes & grill available as add-ons!

Welcome to Lady Liberty, our cozy retreat in downtown Winona, MN! Our recently restored home blends historic charm with modern comforts, perfect for a family or group of up to four. With one bedroom, one bathroom, and a spacious living area, it’s designed for relaxation and connection. Just blocks from local cafes, shops, and the scenic Mississippi River, you’ll find endless opportunities to explore. Book now for a memorable stay—we can’t wait to host you! – Jaime and Allison

Treetops Suite, 2 bedrooms @ 7th Street Retreat

Treetops Suite for Four is the perfect weekend getaway, conveniently located in the heart of Winona and only a 7-minute walk from the train station. The self check-in apartment has a secure keypad entrance. 2 bedrooms, 1 double bed and 2 twin beds, bathroom w/shower, kitchenette and sitting area. Wi-Fi; Cable, Netflix/Prime/DVD player. Please use caution on the steep steps to the apartment. There is a hand railing. We are located three blocks from a charging station.

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.

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.