Vacation rentals in Winona

4.99 out of 5 average rating, 713 reviews

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

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

4.9 out of 5 average rating, 192 reviews

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

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.

4.95 out of 5 average rating, 234 reviews

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

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.

4.99 out of 5 average rating, 226 reviews

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!

4.92 out of 5 average rating, 267 reviews

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

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!

4.95 out of 5 average rating, 131 reviews

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

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.

4.98 out of 5 average rating, 131 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 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.

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.

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.

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.

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.

4.96 out of 5 average rating, 140 reviews

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

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.

4.99 out of 5 average rating, 159 reviews

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

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.

4.98 out of 5 average rating, 402 reviews

An open den area features a futon couch and a coffee table, complemented by a desk with a chair. A television is positioned on a stand, visibly showing programming. Two windows allow natural light, while a lamp provides additional illumination in the cozy space.

Loft in Winona

Winona West End Loft

A roomy, but cozy upstairs loft with den, kitchen, bedroom with new queen bed, and full bath. The futon couch in the den can be made into a full size bed. Guest wifi and television with cable included. Shared entrance with homeowner but completely private space with locked door at top of main stairs.

Vacation rentals for every style

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A space thats all yours, with room for everyone

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Convenient locations with everyday essentials

Popular amenities for Winona vacation rentals

Vacation rentals with pools in Winona

A serene bedroom features a spacious bed with light bedding, complemented by a blue carpet. A rocking chair is positioned near a sliding glass door, providing views of the river and trees outside. An art piece with colorful balloons adds a touch of decor.

Private room in Brownsville

4.97 out of 5 average rating, 31 reviews

Mississippi River View

4.97 out of 5 average rating, 30 reviews

A modern, single-story house is set among lush greenery, featuring a welcoming front porch with steps leading to the entrance. A driveway accommodates vehicles, while the yard is adorned with well-maintained grass and a variety of plants. Nearby structures are visible, contributing to the neighborhood's charm.

Home in La Crosse

Brand New, 3 Bed/ 2 Bath w/ Parking on UWL Campus

A cozy hotel room features two queen beds with neutral-toned bedding and decorative throw blankets. A wooden dresser and a comfortable chair are present, while wall art and soft lighting create a relaxed atmosphere. A window allows natural light to enter the space.

Hotel room in Onalaska

4.75 out of 5 average rating, 4 reviews

Deluxe 2 Queen, Stoney Creek Onalaska, Parking

Superhost

Tiny home in La Crosse

4.86 out of 5 average rating, 188 reviews

Come unwind with us at Kindred Tiny House.

A rustic corner of the room features a wooden desk accompanied by a chair and a dresser with multiple drawers. A TV is housed in a unit made of natural wood. A slatted door allows natural light to enter the space, creating a welcoming atmosphere.

Hotel room in Onalaska

Expanded King w/ Whirlpool! Stoney Creek Onalaska

Superhost

A spacious deck surrounds a large above-ground pool, featuring a safety railing and a shaded area from a large sun sail. Lounge chairs are positioned nearby, inviting relaxation in a peaceful outdoor setting.

Home in Onalaska

4.83 out of 5 average rating, 23 reviews

Secluded home w/pool, hot tub, cold plunge & sauna

Hotel room in La Crosse

4.54 out of 5 average rating, 114 reviews

Suite in Hotel

An inviting outdoor swimming pool is framed by a spacious wooden deck. Several blue umbrellas provide shade for the nearby seating area. Lush greenery and hills form a natural backdrop, enhancing the serene atmosphere of the secluded log home.

Home in Alma

4.76 out of 5 average rating, 17 reviews

The Shack

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Other great vacation rentals in Winona

Guest suite in Coon Valley

A yellow trail sign is affixed to a tree, featuring a silhouette of a walking figure. The background showcases a lush green forest, with trees and foliage creating a serene, natural environment.

4.96 out of 5 average rating, 52 reviews

Loghome studio/10 mn to LaCrosse - wk/mo discounts

4.94 out of 5 average rating, 62 reviews

A stylish bathroom features a modern vanity with ample storage, complemented by a circular mirror. A neatly placed toilet and clean lines create a functional space. Soft wood flooring adds warmth, while neutral cabinetry ties in with the overall design aesthetic.

Home in Fountain City

Our Little River House

5 out of 5 average rating, 32 reviews

Wood-fired pizzas are seen baking in an oven with a brick archway. Flickering flames provide a warm glow, emphasizing the textured crusts topped with various ingredients. The oven's interior features a rustic stone base, complementing the inviting atmosphere of the cooking process.

Guest suite in Cochrane

Lower Level Farmhouse at Suncrest Pizza Farm

5 out of 5 average rating, 38 reviews

A dining area featuring a wooden table with seating for four is positioned beside large windows offering expansive views of the Mississippi River and surrounding greenery. A coffee station is nearby, complemented by a lamp and chandelier for added light.

Home in Minneiska

Riverview Radiance: 5BR, Scenic Views, Pets OK

A renovated home features a blend of dark siding and light wood paneling. Large windows allow natural light to fill the facade, while an ornate iron gate and pathway lead to the entrance. The lawn is well-kept, enhancing the inviting appearance.

4.9 out of 5 average rating, 42 reviews

The Broadway Exchange

A covered porch features two comfortable wicker chairs with light grey cushions, positioned to offer views of the Mississippi River. Lush greenery lines the riverbank, while a sense of tranquility is provided by the expansive water and sky.

5 out of 5 average rating, 15 reviews

Waterfront | HOT TUB | Sleeps 15

Superhost

A sliding glass door provides access to a wooden deck, framed by two outdoor chairs with floral cushions. The reflective surface of the door showcases greenery outside, while a propane grill is visible on the deck.

Cabin in Trempealeau

4.81 out of 5 average rating, 77 reviews

Grand River Shack Retreat