Vacation rentals with outdoor seating in Winona

4.9 out of 5 average rating, 198 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.

4.99 out of 5 average rating, 238 reviews

A spacious dining area features a large black table surrounded by six teal chairs, placed on a striped rug. A vibrant window seat adds color, while a chandelier hangs above, contributing to the room's inviting ambiance. The kitchen can be seen in the background.

Bungalow in Winona

*Prairie Island Bungalow with Water Access*

Welcome to Prairie Island Bungalow (PIB)! Located on Prairie Island in Winona, this home provides the perfect, quiet getaway for work or play, and is your gateway to outdoor adventure in the Winona area. River access is available on our private dock next door! With thoughtful amenities including a fully-stocked kitchen (with coffee and tea!), plush linens, Smart TVs, games and books, a fire pit, snowshoes, and kayak and canoe rentals; we invite you to simply show up and enjoy your stay at PIB!

4.93 out of 5 average rating, 290 reviews

The cozy kitchen and dining area features light-colored cabinetry and a large countertop. A round table with four red chairs is positioned beneath a wall art piece. Warm wooden paneling lines the walls, complementing the inviting atmosphere.

Farm stay in Dakota

The Bungalow at the Healing Refuge

Welcome to The Healing Refuge! Come experience life on a Minnesota farm nestled in the rolling hills of the Driftless region. Relax out on the deck, swing in a hammock among the trees, or enjoy a walk through our beautiful cover crop fields. This is a working farm and depending on the season, you are welcome to help collect eggs, learn from the horses, observe the farm animals, and find out about regenerative agriculture. We want your experience at our farm to be relaxing and refreshing!

4.98 out of 5 average rating, 130 reviews

A view of the Mississippi River is seen from the apartment, with lush green bluffs in the background. Nearby buildings exhibit charming architecture, and parked cars line the streets. A light post adorned with an American flag stands in the foreground.

Apartment in Trempealeau

Small Town Vibes with Amazing River & Bluff Views

Enjoy gorgeous view of the Mississippi River, bluffs, and trains, entertain yourself with the live music (occasionally late) from neighboring establishments, stargaze on the deck, or revel in the passing trains. This apartment is the perfect place to get away and relax. Bring up your boat as you'll have parking available in the driveway too! NOTE: this is an upstairs apartment, but we promise you won't be disappointed and want to come back again and again. NON SMOKING. No pets.

4.97 out of 5 average rating, 146 reviews

The two-story blue duplex stands amidst greenery, showcasing a covered entryway and a small deck. Windows allow for natural light, while the surrounding fence enhances privacy. The backdrop includes the undulating landscape of the Mississippi River, visible on clear days.

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.

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, 253 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 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.

4.97 out of 5 average rating, 193 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!

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.

4.95 out of 5 average rating, 149 reviews

The interior of the tiny house features a cozy seating area with two individuals engaged in conversation. A small table is positioned near a well-equipped kitchen area, which includes a stove. Natural light fills the space through large windows, complemented by colorful artwork on the walls.

Tiny home in Winona

Potluck String Lodge (PSL)

Potluck String Lodge (PSL) is situated within Prairie Island Campground along 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 Boats and Bluegrass music festival and one of the campground picking circles hosted by the Potluck String Band.

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.

4.93 out of 5 average rating, 181 reviews

Spacious Retreat for 1-8 guests

Staying with us for work or pleasure, this tranquil home is sure to suit all your needs. It has been renovated with charm and comfort in mind. All the modern indoor amenities will make you feel at home. Outdoors, enjoy the fully fenced in yard for privacy. It is conveniently located near Winona’s outdoor recreation, shopping, hospital and more.