House vacation rentals in Winona

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Top-rated house rentals in Winona

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Guest favorite

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

4.96 out of 5 average rating, 100 reviews

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!

Guest favorite

A spacious bed with a brass headboard is center-stage in the room, accented by layers of blue and white bedding. Nightstands with lamps are placed on either side, contributing to the overall balanced layout. Soft curtains frame a window, allowing natural light to fill the space.

Home in Minnesota City

4.98 out of 5 average rating, 296 reviews

✨Vintage Lustron Home✨

Enjoy a stay in this vintage Lustron Home. It is a unique home. It has two bedrooms, and a sofa sleeper in the living room. The master bedroom has a queen size bed. The second bedroom has two twin beds. This home offers a washer and dryer for your convenience. It has a large fenced yard to enjoy during your stay. Off street parking and Wi-Fi included. This home is in a very peaceful neighborhood. Located close to Winona State University and St. Mary's University. There are State Parks close also

Guest favorite

A two-story house is set among vibrant autumn foliage. Large windows offer natural light and scenic views of the surrounding landscape. A gravel path leads up to a wooden staircase, with a grassy area extending towards a verdant valley in the background.

Home in Rushford

4.9 out of 5 average rating, 188 reviews

Country Cottage in SE MN Bluff Country near Winona

Experience the beauty SE MN & the Driftless Region. We are located in the beautiful and secluded Wiscoy Valley which straddles the boundaries of Rushford and Winona, MN. Surrounding area includes small towns, rolling valleys, sparkling creeks, and short drives to the Mississippi and Root rivers. Located 53 miles from Rochester, MN, 12 from Winona, MN, and 30 from LaCrosse, WI. *This is a very private N/S space with 3 stairs to access the first floor. Cell service varies but. v. good internet.

Guest favorite

A spacious deck extends from the retreat, featuring comfortable seating and a glass railing for unobstructed views of the surrounding nature. Warm sunlight bathes the deck, highlighting the wood tones and inviting a serene atmosphere.

Home in Mindoro

4.97 out of 5 average rating, 120 reviews

Stunning Views! - Wanlass @HighPointRetreats

Perched in the solitude of nature, our ridge top retreat 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 one-of-a-kind private duplex. Wanlass retreat is named after Wanlass Summit located north, just steps away from this retreat. Wanlass sleeps four-five and is non-smoking. Get your front row sunset seats and relax in the soaker tub. Immerse yourself in tranquility and come stay with us.

Guest favorite

A serene backyard setting features tall trees adorned with autumn leaves, gently illuminated by the soft light of dusk. A peaceful lake is visible in the background, reflecting the warm hues of the sunset. A carpet of fallen leaves covers the ground, enhancing the tranquil atmosphere.

Home in Onalaska

4.94 out of 5 average rating, 154 reviews

Little House on the Prairie

Enjoy this newly remodeled 2 bedroom 1 bath house located on beautiful lake onalaska only minutes from town, but far enough away to enjoy the quiet peacefulness of nature. There is a large backyard with lake access for year round activities (boating, fishing, kayaking, canoeing, and ice fishing. Schaeffer's boat landing and rentals is just a short walk away, and a popular restaurant is also within walking distance. A beautiful walking/biking trail is nearby, and many other attractions.

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

4.95 out of 5 average rating, 129 reviews

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.

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

4.98 out of 5 average rating, 126 reviews

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.

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

4.91 out of 5 average rating, 244 reviews

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.

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

4.98 out of 5 average rating, 171 reviews

~ 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!

Guest favorite

A hot tub with illuminated features is positioned outdoors, overlooking a serene lake. An impressive sunset creates a gradient of colors in the sky, and silhouettes of trees line the horizon. The peaceful atmosphere invites relaxation and enjoyment of the natural beauty.

Home in Pepin

4.96 out of 5 average rating, 101 reviews

Scenic, waterfront home on Lake Pepin with HOT TUB

Welcome to our newly renovated Pepin lake house! The perfect place for a couples getaway, friends weekend, family vacation, and everything in between. Enjoy the beautiful panoramic view of Lake Pepin from the front window while sipping a cozy cup of coffee, or watch the sunset with a glass of wine around a bonfire. The spacious dining room and kitchen are perfect for sharing a warm meal with loved ones, while the bar/living room promises a good time!

Guest favorite

The exterior of the lodge is shown from a distance, with the building set on a slight hill. Two trees with vibrant autumn foliage flank the structure, and a covered deck extends along part of the front. A clear blue sky provides a contrasting backdrop.

Home in Arcadia

4.95 out of 5 average rating, 157 reviews

Sonney Lodge

Perched on a hilltop in scenic Newcomb Valley, Sonney Lodge provides a quiet, country setting while still only a 10 minute drive to downtown Arcadia. Located on a dead end with a private drive and no through traffic, the lodge features 3 bedrooms, 2 bathrooms, a full kitchen, dining room and lower level entertainment room. A covered deck wraps around 2 sides of the home offering spectacular views of the surrounding hills and countryside.

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

4.97 out of 5 average rating, 152 reviews

Beautiful Views of the Mississippi river

This spacious 6300 sf home sits on 18 wooded acres and overlooks the Mississippi and is ideal for large groups. We can accommodate up to 14 guests. 5 bedrooms with 10 total beds. 2 kings, 3 queens, 5 twins. There’s also a pull out couch and additional mattresses. Large, fully stocked kitchen. 2 refrigerators and 3 large living rooms. Coffee maker and coffee. We have one outdoor security camera. Sorry, No pets.