Family-friendly vacation rentals in Winona County

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Top-rated family-friendly rentals in Winona County

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A wooden tray is positioned on a neatly made bed, featuring a bottle of rose wine and two wine glasses. A small vase with a sprig of greenery adds a touch of freshness, complementing the subtle colors of the decorative pillows and bedspread.

Home in Galesville

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.

FamilyIndoor spacesSleep quality

4.95 out of 5 average rating, 126 reviews

Top guest favorite

A cozy living room is showcased, featuring a wood-burning stove positioned on a stone base with stacked firewood. A light-colored sofa is seen, with a decorative floor lamp nearby. The walls are painted in neutral tones, enhancing the room's relaxing ambiance.

Cottage in Winona

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.

FamilyKitchenOutdoor spaces

4.92 out of 5 average rating, 117 reviews

Guest favorite

A serene view of the Mississippi River is captured, featuring a boat and a paddleboarder on calm waters. Lush green trees line the riverbanks, while gentle hills rise in the background under a cloudy sky.

Home in Fountain City

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.

KitchenIndoor spacesBiking

4.96 out of 5 average rating, 160 reviews

Top guest favorite

The exterior of the farmhouse is showcased, featuring a traditional two-story structure with a large front porch supported by dark columns. Lush green grass surrounds the home, complemented by tall trees in the background, enhancing the serene country environment.

Farm stay in Houston

30 Acre Private Farm W/ Walking Trails - Sleeps 10

Welcome to Smith Family Farm! Our 5th-generation Family Farm was built in 1876 and beautifully renovated. This historic 30-acre retreat offers the perfect blend of peace and play. Located about 5 miles off I-90, we feature a 7-hole disc golf course, private walking trails, and a sun-drenched deck for morning coffee. With space for 10 guests, a Blackstone griddle, and a cozy fire pit, it’s the ultimate Minnesota getaway for families and friends. Come make your own history at the farm!

Indoor spacesFamilyParks

4.98 out of 5 average rating, 159 reviews

Guest favorite

The expansive home is nestled among a vibrant forest of fall foliage, showcasing a rich palette of oranges, yellows, and greens. Large windows reflect the natural beauty surrounding the property, offering a serene view of the landscape.

Home in Winona

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!!!

KitchenFamilyValue

4.96 out of 5 average rating, 210 reviews

Superhost

A three-story cabin is nestled among lush greenery, featuring a brown exterior that blends with the natural surroundings. Two seating areas are visible on the patio, inviting relaxation. The sloped roof and large windows provide an open and airy feel to the structure.

Cabin in Winona

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.

FamilyKitchenCheckout

4.78 out of 5 average rating, 184 reviews

Top guest favorite

A private deck is seen on the upper level, adorned with vibrant flower pots and surrounded by greenery. The view extends towards the Mississippi River and distant bluffs, framed by trees that provide natural shade.

Home in Fountain City

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.

FamilyIndoor spacesNearby

4.98 out of 5 average rating, 204 reviews

Top guest favorite

A spacious sitting area showcases a comfortable green couch accompanied by decorative pillows. A wooden coffee table sits in front, with a bookshelf and a floral armchair nearby. Soft lighting from the lamps and a nearby window creates a warm ambiance.

Apartment in Winona

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.

FamilyKitchenWifi

4.89 out of 5 average rating, 104 reviews

Guest favorite

A charming cabin is seen nestled among vibrant autumn foliage along the Mississippi River. The structure is surrounded by a mix of trees displaying warm seasonal colors, with a boat gently gliding across the river in the foreground.

Home in Winona

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.

KitchenIndoor spacesLocation

4.91 out of 5 average rating, 287 reviews

Top guest favorite

The living room features exposed brick walls and wooden beams overhead. A spacious couch is complemented by two chairs, while a coffee table sits atop an area rug. Natural light fills the space through large windows that offer views of the outdoor patio.

Home in Winona

~ 71 Johnson Street ~

This beautiful brownstone house is conveniently located in the heart of beautiful downtown Winona MN! It is within close proximity to many attractions Winona has to offer such as: Mississippi River front access, coffee shops, restaurants, bars & lounges, Winona State University, Lake Winona, hiking/biking trails, Shakespeare Festival, Minnesota Marine Art Museum, and much more! Please allow us to make your next stay in beautiful Winona a memorable one!

Indoor spacesKitchenLocation

4.98 out of 5 average rating, 265 reviews

Guest favorite

Apartment in Winona

1 Bedroom with Extra Amenities, Quiet Neighborhood

Our light-filled two-bedroom apartment is the perfect home away from home in Winona. * Spacious main bedroom with queen size bed * Second bedroom with twin daybed and 90s throwback CRTV * 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

KitchenIndoor spacesParking

4.95 out of 5 average rating, 290 reviews

Guest favorite

The exterior of a contemporary tiny house is shown, featuring a mix of wood and metal siding. A small patio area includes a black seating arrangement and a storage box. A covered grill area is visible nearby, surrounded by grassy landscaping.

Tiny home in Winona

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.

KitchenIndoor spacesNearby

4.94 out of 5 average rating, 114 reviews