Vacation rentals in Winona

4.99 out of 5 average rating, 155 reviews

A wooden deck features a metal table set in the center, with two glasses placed on top. The expansive view overlooks lush green hills and winding rivers under a clear blue sky.

Home in Reads Landing

Gorgeous home overlooking the Mississippi River

Gorgeous, secluded home moments away from Wabasha. Free WiFi. Enjoy Septoberfest, one of the many terrific restaurants in the area, Music Under the Bridge, or any other fun activity this little river town has to offer. The house is fully furnished, with two bedrooms, but with room to sleep more. This is a one-of-a-kind property with a view that could only best be described by simply reading our reviews. Located south of Red Wing, between Lake City and Wabasha, in Reads Landing, Minnesota.

5 out of 5 average rating, 16 reviews

A spacious porch wraps around the home, featuring several chairs and a table. The structure is supported by white columns, offering a shaded area for relaxation. Lush green grass surrounds the porch, creating a serene outdoor space complemented by a clear blue sky.

Farm stay in Rushford

Country Chic, Hovde Home at Labrador Farm

Come enjoy the peaceful surroundings of this rustic destination. Surrounded by nature and coupled with many modern luxuries. Breathtaking views from the porches. Cozy up at the fire pit to stargaze or roast some marshmallows. Offload horses, paddock available with water (4-6 with signed waiver). Bring your furry-faced family members ! Do not leave on the property unattended please. Pets are welcome but must be supervised. There is a fee PER pet but all Dogs welcome! Enjoy our hidden gem!

4.92 out of 5 average rating, 246 reviews

A rustic cabin is situated among greenery, featuring a stone path leading to a fire pit surrounded by light blue chairs. The cabin has a covered porch and a large window, providing a connection to the natural landscape.

Cottage in Stoddard

Stylish 1 bedroom cottage on the Mississippi River

This unique place has a style all its own. Conveniently located by the Mississippi River and highway 35. The place gives you a cabin feel close to La Crosse! Goose Island is 5 minutes away. Great spot for bird watching, fishing, kayaking, boat launches, hiking or frisbee golf. Mt. La Crosse is super close to enjoy skiing/snowboarding. 15 minute drive to downtown La Crosse and 3 miles North of Stoddard puts you in a great central location for the area. Pets are welcome. No cleaning fee!

4.96 out of 5 average rating, 176 reviews

The open living area features wooden walls and floors, creating a warm, rustic feel. A dining table is positioned centrally, surrounded by red chairs. Stairs lead to a loft area, adorned with quilts. Natural light enters through multiple windows, enhancing the inviting ambiance.

Cabin in Viroqua

Cabin-Driftless/Near Lakes/Streams/Pet Friendly

Perfect place to escape into nature at our cozy country cabin that is fully furnished. Our cabin is conveniently located 1.5 miles outside of Viroqua on a secluded township road, near premier trout fishing creeks and outdoor adventures. The cabin boasts a large wrap around deck. Perfect spot to relax with sounds of nature and views of the Valley. Inside this modern cabin is a loft with a king and 2 XL twins, main level bedroom with full bed and a full size sofa sleeper. H.S internet.

4.97 out of 5 average rating, 107 reviews

Cabin in Mindoro

Stunning Views! - Pettinger @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. Pettinger cabin is named after Petting Summit located just east of the cabin. Pettinger 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.

4.96 out of 5 average rating, 119 reviews

A spacious two-story building is shown with a metal roof and a welcoming front porch. Colorful hanging flower planters add vibrancy, and outdoor seating is arranged near the entrance. The surrounding grassy area offers a relaxed, natural setting.

Guesthouse in Hixton

Country Retreat. Beautiful sunsets and sunrises.

Fresh country air. Beautiful view. Cable TV. Wi-Fi. Hot Tub (chemical free). Spacious furnished kitchen. Sectional sofa with recliners. Recliner. Electric fireplace. Outdoor firepit (bring your own wood). Washer and dryer. 12 inch step into tub/shower. This beautiful getaway is attached to the family business shop. We do load trailers occasionally and will be working in shop at times. Minimal noise. 30 Minutes from Eau Claire. We are only 25 minutes from two lakes with beaches.

5 out of 5 average rating, 24 reviews

The exterior of a charming vacation home is presented, featuring a combination of gray siding and large windows. A wooden deck with a table and four chairs is shaded by a blue umbrella. Adirondack chairs are placed nearby, and a decorative ship's wheel adds a nautical touch.

Home in Lake City

"Amazing Views" of Lake Pepin in Lake City

Amazing Views is Lake City's "Premiere" Vacation Rental! From its perfect location, to the absolutely Amazing Views and lake cottage feel, you will love this home! Enjoy Adirondack chairs under the pergola in the summer to watch the eagles, pelicans and sailboats. Cuddle up by the red brick, gas fireplace in the living room in the winter. A perfect home for every season. Just 2 blocks away from Ohuta Beach and the Marina. Bring your friends and family to this "Amazing" home!

4.79 out of 5 average rating, 195 reviews

A charcoal grill is positioned on a wooden deck overlooking a calm body of water. A dock extends into the water, with two individuals seen raising a kayak in the distance. Lush greenery is visible nearby under a partly cloudy sky.

Chalet in La Crosse

Bayfront Chalet on Richmond Bay

Waterfront Property- 3 bedrooms, 2 full bath home - You will be amazed at the views from this extravagant French Island house on Richmond Bay. It features JennAir stainless steel appliances including dishwasher, laundry, central air, free Wifi, large deck and use of a nice sized dock for boating, kayaking or jet skiing. These items (boat,kayak,water crafts)are not included with . Airbnb. Fireplace is for aesthetics. Less than a 10 minute drive to the La Crosse Center.

4.9 out of 5 average rating, 241 reviews

A spacious window with multiple panes offers views of the Mississippi River and surrounding greenery. Candles are placed along the wooden ledge, providing a serene ambiance. Natural light fills the room, highlighting the tranquil setting beyond.

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.

5 out of 5 average rating, 24 reviews

A spacious outdoor deck features a large red umbrella and ample seating, surrounded by lush greenery. The deck is accessible from the home, providing a seamless connection to the natural surroundings.

Home in La Crosse

Luxury Retreat Nestled in Bluffs -10 Mins Downtown

Newly renovated luxury home nestled in the bluffs of scenic La Crosse. Conveniently located 10 minutes to downtown La Crosse. Enjoy the vaulted wood beam ceilings and stunning views. Cozy up in the living room by the fireplace and revel at beauty and seclusion of the nature that surrounds you. Every detail has been thoughtfully curated to ensure comfort, relaxation, and fun. Expansive outdoor spaces.

4.98 out of 5 average rating, 227 reviews

A back deck with a river view is furnished with two comfortable chairs and a small table, allowing for relaxation and enjoyment of the scenic landscape. The backdrop features lush trees and the Mississippi River, with a bridge visible in the distance under a clear blue sky.

Apartment in Wabasha

Spacious River View 2 br apt near Eagle Center

This gorgeous fully renovated 2 br apt unit is a hidden gem located in the heart of Wabasha. Enjoy walking to your favorite destinations such as the Eagle Center & downtown's best restaurants. Features: -Historical elegance -Footsteps from the Mississippi River & the new Eagle Center bandstand -Fully furnished -2 br/2 bath -New kitchen -Spacious living/dining room -Fireplace -Large deck w/ river view

4.81 out of 5 average rating, 102 reviews

A modern kitchen space is highlighted by dark cabinetry and sleek granite countertops. Stainless steel appliances, including a refrigerator and stove, are present. Glassware is arranged on a shelf above the sink, providing utility and convenience.

Home in Onalaska

Backwater hideaway. Big house with water access.

Lovely house with tons of space. Located on Brice Prairie, this house sits on a back stream of the mighty Mississippi/lake Onalaska. Accessible by flat bottom boat, kayak or similar. Not a great swimming spot with being often a bit weedy. Great ice fishing just down a bit and a large fenced in back yard. House has two kitchens, formal dining, large deck, rec area with kids items.

Vacation rentals for every style

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Kick off your hiking boots at these rustic lodgings

Popular amenities for Winona vacation rentals

Stay near Winona's top sights

Minnesota Marine Art Museum32 locals recommend

Garvin Heights Lookout17 locals recommend

Island City Brewing Company Co14 locals recommend

Blue Heron Coffeehouse15 locals recommend

Acoustic Cafe15 locals recommend

The Boat House Restaurant14 locals recommend

Vacation rentals with pools in Winona

4.9 out of 5 average rating, 163 reviews

Tiny home in La Crosse

Come unwind with us at Kindred Tiny House.

5 out of 5 average rating, 38 reviews

Two individuals are seated in a green float in the expansive pool, overlooking a vast landscape. The sun shines brightly above, casting reflections on the shimmering water, while rolling hills and trees extend into the distance.

Home in Rochester

RARE! Pool, hot tub, garden &chickens! 4m to Mayo

4.89 out of 5 average rating, 228 reviews

A farmhouse-style kitchen is seen, featuring a large stainless steel sink and a dishwasher. Bright yellow lemon decor hangs on the walls, and a bouquet of colorful flowers rests on a wooden island. The cabinetry is white, complementing the green walls.

Farm stay in Dakota

The Lodge at Heart & Soil Ridge

4.8 out of 5 average rating, 20 reviews

An expansive above-ground pool is surrounded by a wooden deck, featuring lounge chairs and poolside seating. Lush greenery and trees are visible in the background, creating a serene outdoor environment. A basketball hoop and wooden surfaces enhance the recreational space.

Home in Onalaska

Cozy, quiet place w/pool/hot tub

An inviting outdoor swimming pool is framed by a spacious wooden deck. Several blue umbrellas provide shade for the nearby seating area. Lush greenery and hills form a natural backdrop, enhancing the serene atmosphere of the secluded log home.

Home in Alma

4.77 out of 5 average rating, 13 reviews

The Shack

4.99 out of 5 average rating, 75 reviews

A blue above-ground pool is surrounded by a wooden deck, with a ladder providing access. The back of the house is visible, featuring large windows and a spacious deck area. Lush greenery and a nearby umbrella enhance the outdoor setting.

Home in La Crosse

3BR 3BA w/ Hot Tub, near LaX' Top Rated Activities

A view from a balcony shows a lush, green landscape with rolling hills and a serene stream winding through the vegetation. The foreground features a fenced yard with well-maintained grass, bordered by trees and shrubs.

Farm stay in Chatfield

5 out of 5 average rating, 4 reviews

Lost Creek executive home on 200 acre horse ranch

Camper/RV in Zumbro Falls

The Bunkhouse camper is positioned on a grassy area, featuring a covered outdoor space. Several patio chairs are arranged around a fire pit, providing a cozy setting. Trees and greenery are visible in the background, enhancing the natural surroundings.

4.93 out of 5 average rating, 14 reviews

Bunkhouse Camper - Bluff Valley Campground

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Other great vacation rentals in Winona

4.9 out of 5 average rating, 280 reviews

A bright living area features a comfortable couch with yellow accents and a decorative area rug. Large windows allow natural light to fill the room, offering views of the surrounding greenery. Wall art adds a touch of color to the light-toned walls.

Barn in Hixton

A Suite Getaway

5 out of 5 average rating, 12 reviews

A spacious man cave features a wooden ceiling and light-colored walls. A comfortable couch faces a large TV, while a poker table equipped with green felt is surrounded by several black chairs. Decorative antler mounts adorn the walls, adding rustic charm.

Home in Arcadia

Arcadia Cottage

4.75 out of 5 average rating, 8 reviews

The interior space features a wooden staircase leading to an open living area. Natural light fills the room through large windows, highlighting a seating area with couch and chairs. The kitchen and dining space are visible in the background, creating a welcoming environment.

Home in Rochester

Cozy tranquility 6mi from Mayo 4bed/3bath

5 out of 5 average rating, 58 reviews

A charming yellow house with a gray roof is set against a backdrop of colorful autumn trees. Two vibrant red maple trees frame the front of the home, while green fields extend before it, creating a serene country atmosphere.

Home in La Crescent

Country Charm Over River Valley and Horse Farm

4.97 out of 5 average rating, 31 reviews

A modern kitchen features wooden cabinetry and a spacious island with three stools. Stainless steel appliances are neatly arranged, while flowers in a vase add a touch of color. Ample counter space is available for food preparation and cooking.

Home in Blair

Med Park House

4.85 out of 5 average rating, 74 reviews

A calm lake is visible under a twilight sky, with soft hues of pink and purple reflecting on the water's surface. Lush greenery frames the scene, highlighted by silhouettes of trees at the water's edge.

Cottage in Pepin

Scenic View Cottage on the Great River Road

4.93 out of 5 average rating, 44 reviews

A single-story home is shown with a white exterior, featuring large windows and a welcoming front door. A well-maintained lawn with freshly mowed grass surrounds the house, complemented by a flowering tree nearby. A white picket fence encloses the yard.

Home in La Crosse

Comfortable, Hyde Away Home