Vacation rentals in Winona

4.96 out of 5 average rating, 100 reviews

A spacious wooden deck is shown with several comfortable chairs facing the serene waters of Lake Pepin. Soft sunlight reflects on the water, and trees line the edge of the property, creating a peaceful atmosphere for outdoor relaxation.

Home in Pepin

Villa Serra - Lakehouse in Pepin

Villa Serra is located in beautiful Pepin, Wisconsin. This unique 3 bedroom 2 full bath home boasts panoramic views of Lake Pepin. The open floor plan features a spacious living room with adjoining kitchen and breakfast bar island. The dining area leaded to an elevated open porch and deck with expansive views. Stroll through the hillside gardens and relax on the deck overlooking the lake - a perfect setting for gathering, enjoying the gas BBQ and dining al fresco. The perfect Lake Pepin retreat!

4.99 out of 5 average rating, 156 reviews

Large glass doors lead to a private deck, offering an expansive view of the Mississippi River and lush green landscape. The scene captures the tranquility of nature, with the water reflecting the surrounding greenery and distant hills.

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, 17 reviews

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!

4.9 out of 5 average rating, 59 reviews

Home in Frontenac

Charming 3 bed/3bath renovated cabin on Lake Pepin

This is the perfect quiet getaway! High end renovation with 100 ft of private beach on breath-taking Lake Pepin. Revel in this home’s private owner’s suite, sunny open floor plan, wood fireplace, expansive deck, and incredible lake views. *Per local ordinance: 6 guests max over 5yrs old, no parties/events. *No more than 3 vehicles allowed. *No more than 3 additional guests allowed *No recreational vehicles, campers, or tent camping allowed. *Quiet outdoor hours from 9pm-9am. *No fireworks

4.96 out of 5 average rating, 178 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, 121 reviews

A landscaped garden area features a variety of colorful flowers and plants surrounded by lush green grass. A bird feeder stands nearby, with trees in the background and a gentle slope leading to open fields. A hanging basket of purple flowers adds a pop of color.

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, 26 reviews

A shaded outdoor seating area is shown, featuring four red cushioned chairs and a glass-top coffee table. A scenic view of Lake Pepin is visible through large windows, with distant hills and a wide sky creating a calming backdrop.

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, 196 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.

4.97 out of 5 average rating, 37 reviews

A charming cottage appears nestled among lush greenery, framed by vibrant shrubs and foliage. A stone pathway leads to a large window, offering a glimpse of the inviting interior. The sound of leaves rustling adds to the peaceful ambiance of the entrance.

Home in Wabasha

The Cottage

This unique and quaint cottage is a perfect get away for 2. Located a block from the walking path, Isaak Walton park and Parkside Marina, this quiet cottage is a central spot for many activities. Take the walking path to the beach or head downtown to the Eagle Center. This cottage boasts many different plants in its secluded gardens. Sit on the back porch and sip your morning coffee, or take a nice bubble bath in the claw foot tub. You’ll be sure to find solace here.

4.98 out of 5 average rating, 137 reviews

A staircase with wooden stairs features a black-painted riser. Light-filled walls frame a doorway that leads to a combined living and bedroom area in the background. A chair is positioned at a small table to the left, enhancing the inviting flow of the space.

Apartment in Viroqua

Two Bedroom upstairs airy modern apartment

This upper level apartment has beautiful natural light, a combined living/dining space, two well-appointed bedrooms with built-in desks, a fully furnished vintage kitchen, a full bath, and a private deck. It is available at a discounted price for longer stays. This apartment is part of three apartments in an older home but has a private indoor and outdoor access point. Two queen beds, one single bed and one sleeper sofa. Reserved parking by the entry door.

5 out of 5 average rating, 25 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.

Vacation rentals for every style

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Houses

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Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Winona vacation rentals

Stay near Winona's top sights

Minnesota Marine Art Museum11 locals recommend

Garvin Heights Lookout3 locals recommend

Island City Brewing Company Co7 locals recommend

Blue Heron Coffeehouse6 locals recommend

Acoustic Cafe4 locals recommend

The Boat House Restaurant3 locals recommend

Vacation rentals with pools in Winona

4.87 out of 5 average rating, 174 reviews

Tiny home in La Crosse

Come unwind with us at Kindred Tiny House.

An open kitchen area features modern appliances, including a stove and refrigerator. A large island with seating provides a central gathering space. Natural light floods the living area through sliding glass doors, which lead to an outdoor patio with green views.

Apartment in Rochester

4.75 out of 5 average rating, 4 reviews

Luxury 1 bedroom Serenity

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

4.81 out of 5 average rating, 21 reviews

A spacious deck surrounds a large above-ground pool, featuring a safety railing and a shaded area from a large sun sail. Lounge chairs are positioned nearby, inviting relaxation in a peaceful outdoor setting.

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/ Pool & Hot Tub, near Goose Island

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

4.96 out of 5 average rating, 69 reviews

A modern multi-story building is displayed, featuring large glass windows and a combination of brick and smooth facade materials. The entrance is framed by a wide overhang, and surrounding trees add greenery to the welcoming exterior.

Apartment in Rochester

2 bdrm Furnished Apt Across from Saint Marys Hosp

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Other great vacation rentals in Winona

4.9 out of 5 average rating, 282 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

Home in Black River Falls

A welcoming living room features rich brown leather seating arranged around a wooden coffee table. A stone fireplace acts as a focal point, while large windows provide natural light and views of the surrounding greenery. Warm lighting from lamps enhances the cozy ambiance.

4.84 out of 5 average rating, 113 reviews

Casa Bella Rosa - Private Custom Estate

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

4.92 out of 5 average rating, 248 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

4.77 out of 5 average rating, 513 reviews

The image captures a modern shower area featuring neutral-toned tiles arranged in a rectangular pattern. The chrome showerhead is positioned above, alongside a sleek wall-mounted control. A white shower base is visible at the bottom, complemented by tiled walls for a clean, contemporary appearance.

Home in Rochester

5 blocks from Mayo, Adorable Upper Unit

4.99 out of 5 average rating, 101 reviews

A spacious outdoor patio is furnished with comfortable seating arrangements featuring plush cushions and accent pillows. A decorative table sits center stage, surrounded by vibrant flowers. The serene view of the Mississippi River and lush greenery can be seen in the background.

Home in Hager City

Castle Vue Villa & Outdoor Oasis (River Views)

4.94 out of 5 average rating, 47 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