Vacation rentals in Winona County

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Top-rated vacation rentals in Winona County

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Top guest favorite

The bathroom features a cast iron soaker tub and two pedestal sinks with modern fixtures. Elegant tile flooring complements the neutral color scheme, while two area rugs add comfort. Natural light enters through a skylight, enhancing the overall spacious feel of the room.

Loft in Winona

4.99 out of 5 average rating, 713 reviews

Penthouse Retreat-Near Downtown Winona!

Hi! This beautiful loft is conveniently located in the heart of Winona MN! Only a few blocks from the downtown and in close proximity to many other attractions Winona has to offer such as: Coffee, restaurants, a wine bar, 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 extended stay in beautiful Winona a memorable one! * MUST CLIMB STAIRS TO UNIT- LOCATED ON THE 3RD LEVEL

Guest favorite

A gravel driveway leads to a two-story white house nestled among lush greenery. Surrounding trees and wildflowers create a natural setting, while the house features a covered porch that enhances the inviting entrance. A visible house number is posted on a sign beside the driveway.

Home in Rushford

4.9 out of 5 average rating, 192 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 corner of the kitchen is seen, featuring a coffee machine alongside a granite countertop. A unique rack holds an assortment of colorful mugs, adding a touch of vibrancy. Storage canisters are also visible, complementing the compact kitchen setup.

Apartment in Winona

4.95 out of 5 average rating, 234 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

Bungalow in Winona

4.99 out of 5 average rating, 226 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!

Guest favorite

A child reaches out to gentle farm pigs in a grassy field. The pigs, varying in shades of pink and black, are gathered close to a subtle fence, creating a serene scene of interaction between animals and humans. Lush greenery surrounds the area.

Farm stay in Dakota

4.92 out of 5 average rating, 267 reviews

The Cottage at The Healing Refuge

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

Guest favorite

A private deck is shown, featuring a small table with two chairs, overlooking a scenic view of the water and trees. Bright blue skies and distant hills are visible in the background. The deck has wooden flooring and a covered roof.

Home in Fountain City

4.95 out of 5 average rating, 131 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

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

4.98 out of 5 average rating, 131 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

The exterior of a home is shown, featuring a stone facade with a sunroom that includes large windows. Lush greenery surrounds the structure, and a well-maintained lawn is visible in the foreground, offering a serene atmosphere.

Home in Winona

4.91 out of 5 average rating, 248 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

A wooden console table is positioned against a wall, showcasing a woven basket filled with brochures and local guides. A detailed map is spread out beside a binder filled with information about the area, providing resources for guests to explore the surroundings.

Home in Winona

4.99 out of 5 average rating, 75 reviews

The Little Train Depot

The Little Train Depot is a comfortable space for you to relax while visiting the quaint river town of Winona. There are a number of things to do in the area including; the Midwest Music Festival, Great River Shakespeare Festival, Frozen River Film Festival, boating on the Mississippi, visiting our local museums or vineyards, enjoy the unique Lark Toys, shops with local artisans, visiting our weekly farmers market or just relax by the lakes.

Guest favorite

Large glass doors open to reveal a winter landscape, showcasing a snow-covered outdoor patio with two chairs. The scene features a distant view of the Mississippi River and surrounding hills under a gray sky.

Home in Winona

4.97 out of 5 average rating, 156 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

A map of Prairie Island Campground displays the layout of campsites, parking areas, and surrounding features. The Mississippi River and various cabins are marked, providing a clear view of the campground's organization and access points.

Tiny home in Winona

4.96 out of 5 average rating, 140 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

An antique wooden cart is positioned in a grassy area, adorned with flowers and plants. A small structure resembling a house sits atop the cart, complemented by a flowering tree nearby. The scenic landscape includes rolling hills in the background.

Loft in Arcadia

4.99 out of 5 average rating, 159 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.