House vacation rentals in Winona

4.96 out of 5 average rating, 114 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!

4.98 out of 5 average rating, 304 reviews

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

✨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

4.9 out of 5 average rating, 199 reviews

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

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.

4.96 out of 5 average rating, 137 reviews

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.

4.97 out of 5 average rating, 148 reviews

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 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.

4.96 out of 5 average rating, 253 reviews

A vibrant display of pink flowers frames the foreground, leading the eye to a classic red barn standing against a clear blue sky. A windmill can be seen in the background, enhancing the rural atmosphere of the property.

Home in Stockholm

Bogus Valley Holm Country/Farm Pepin/Stockholm

Come to the country and enjoy lodging at quiet Bogus Valley Holm. Located in picturesque Bogus Valley between Pepin and Stockholm Wisconsin. This vintage home was built in the mid 1850s and has old world character architecture with the comforts of modern day amenities. The southern exposure enclosed front porch is the favorite gathering spot for most everyone that has stayed in the home. This 2 bedroom 1 1/2 bath property has potential for sleeping up to 8 guests.

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.

4.91 out of 5 average rating, 254 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.

The exterior of a charming brownstone house is presented, featuring traditional brick walls, large black-framed windows, and a welcoming entrance with stone steps. Planters with greenery adorn the entryway, adding a touch of nature to the urban setting.

4.97 out of 5 average rating, 195 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!

4.95 out of 5 average rating, 169 reviews

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

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.

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.

4.96 out of 5 average rating, 170 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.

The exterior of a renovated two-story home is shown, featuring light grey siding and a welcoming aqua front door. A concrete pathway leads to the entrance, complemented by neatly landscaped grass and plant beds. An oversized window allows natural light into the upper level.

4.99 out of 5 average rating, 103 reviews

Ellie’s Place

This historic Winona home has gone through a complete renovation to make your stay enjoyable. It is in close proximity to many of the attractions that make Winona special: hiking/biking trails, Winona State University, Mississippi River, coffee shops, restaurants, bars, Lake Winona, Saint Mary’s University, Minnesota Marine Art Museum, music festivals, the winter ice wall and so much more.

A charming house is depicted with dark grey siding and a steeply pitched roof. Large windows provide ample natural light, framed by white trim. A white front door serves as the focal point, flanked by lantern-style lights. Flower pots enhance the welcoming entrance.