Vacation rentals in Winona County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winona County

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

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, 197 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

The bedroom features a queen size bed with white bedding and decorative pillows. A bench sits at the foot of the bed, and a nightstand with a lamp is located beside it. A piece of wall art adds character, while curtains provide light control.

Apartment in Winona

4.95 out of 5 average rating, 246 reviews

2nd Floor Retreat - 7 Blocks from WSU

Our one-bedroom apartment is perfect for two guests. * NO cleaning fee/deposit required * Spacious bedroom with queen size bed, couch and workspace * Fully kitchen with oven, refrigerator, microwave + coffee/tea station * TV, board games and books * All amenities needed for a comfortable stay * Walking distance to WSU and Cotter * Your own washer dryer in the apartment * Easy self-check-in process We want you to love your time in Winona and are here to make your stay as pleasant as possible.

Top guest favorite

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

4.99 out of 5 average rating, 238 reviews

*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!

Top guest favorite

A spacious living area features hardwood flooring and high ceilings with exposed beams. Large windows allow natural light to fill the space. Seating includes a full-size couch and armchair, with a decorative area rug and a small coffee table complementing the room.

Apartment in Winona

4.97 out of 5 average rating, 199 reviews

~ Third Street Suites ~ #6

This beautiful 3rd story penthouse apartment (ACCESSED BY STAIRS ONLY UP TO THE 3RD STORY) is conveniently located in the heart of downtown Winona MN! Everything Winona and the downtown area has to offer is within close proximity. Examples include: Coffee, restaurants, bars, brewery, Winona State University, Mississippi River, Lake Winona, hiking 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

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

4.93 out of 5 average rating, 288 reviews

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!

Top guest favorite

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

4.98 out of 5 average rating, 129 reviews

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.

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

4.97 out of 5 average rating, 144 reviews

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.

Guest favorite

A serene view captures a calm water surface reflecting sunlight. A private dock extends into the water, surrounded by tree trunks and grass. In the foreground, a wooden table rests next to a wooden fence, while a shed is partially visible in the background.

Cabin in Onalaska

4.92 out of 5 average rating, 111 reviews

Backwaters lodge

This cabin sits overlooking a beautiful view of the water where you will see all types of wildlife. The eagles sit in the giant oak trees just off the porch. Walk down to the dock and drop a line in for fishing. .The state bike/snowmobile/hiking trail is within 3 minutes. The boat landing is 1 mile away. You have your own private dock. We also just added a hatchet throwing target We charge a 25.00 per visit pet fee.

Top 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

4.96 out of 5 average rating, 168 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.

Guest favorite

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

4.95 out of 5 average rating, 149 reviews

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.

Top guest favorite

A scenic view displays the homestead surrounded by rolling hills and fields. The vintage white house is complemented by several outbuildings. Autumn colors are highlighted in the trees and grass, with a driveway leading through a yard with lush greenery.

Loft in Arcadia

4.99 out of 5 average rating, 167 reviews

Tamarack Point Homestead

Tamarack Point Homestead is located between Arcadia, WI and Centerville, WI in the beautiful valley of Tamarack. This scenic 150 year old homestead has an outbuilding loft that allows you to enjoy the country lifestyle and experience the best that Trempealeau County has to offer. Certified to operate by the Trempealeau County Health Department.

Top guest favorite

The kitchen features modern white cabinetry paired with dark countertops. A stainless steel range and hood are installed, with a window above offering natural light. A patterned rug lies on the floor, and potted plants are placed on the windowsill.

Home in Winona

4.99 out of 5 average rating, 306 reviews

Burton House (Downtown Winona)

The Burton House is a recently renovated, cozy little home just a few blocks from downtown Winona, MN and the mighty Mississippi River. It is walking distance to several restaurants, bars and shops. It's the perfect launch pad for outdoor enthusiasts, with wonderful recreation opportunities in and around Winona.