Family-friendly holiday 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!

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!!!

Creekside Cabin

Looking for a getaway? Come to the Creekside cabin just outside city limits to test out "Tiny House Living"! All the amenities of home only smaller. This is a great place! Sit by the creek and listen to the water run or cozy up to the "Tiny" wood burning fireplace to get away from it all. Situated right on the Minnesota State Snowmobile trails. Trails also great for walking/4 wheeling/biking. Please note: you are not by yourself. We live on the property Pets not allowed.

Haven on Huff

Your spacious oasis in central Winona welcomes you for a peaceful and relaxing stay. Haven on Huff is a single family home, adjacent to Winona State University and nearby all the amenities of Winona. Enjoy a large kitchen with dining area, living room with pull-out sofa, and a dedicated office space with desk, TV and chaise that can sleep 1 person. Reserved parking area for multiple cars and a seasonal private patio with grill and seating area tucked away behind the house.

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.

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!

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.