Vacation rentals in Winona

4.9 out of 5 average rating, 189 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, 229 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, 222 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!

4.94 out of 5 average rating, 281 reviews

A child stands in an open field, holding a small black chick in both hands. The background features a soft blue sky with gentle clouds, creating a serene outdoor 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!

4.95 out of 5 average rating, 130 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.

4.77 out of 5 average rating, 173 reviews

A modern kitchen area with floral wallpaper features a dining table surrounded by four chairs. A sleek refrigerator is visible, along with a stove, sink, and ample cabinet space. Natural light fills the space, creating a bright and functional atmosphere.

Cabin in Winona

Creekside Cabin

Looking for a getaway? Come to the Creekside cabin just outside city limits to test out "Tiny House Living"! All the amenities of home only smaller. This is a great place! Sit by the creek and listen to the water run or cozy up to the "Tiny" wood burning fireplace to get away from it all. Situated right on the Minnesota State Snowmobile trails. Trails also great for walking/4 wheeling/biking. Please note: you are not by yourself. We live on the property Pets not allowed.

4.98 out of 5 average rating, 129 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.

4.91 out of 5 average rating, 245 reviews

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

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.

4.98 out of 5 average rating, 337 reviews

A white entrance door is framed by decorative molding, showcasing the unit number 8 prominently displayed. A modern security lock is installed beside the door handle. A small welcome mat lies on the floor, leading to the entrance.

Apartment in Winona

~ Third Street Suites ~ #8

Hi! This beautiful main level apartment is conveniently located in the heart of downtown Winona MN! Everything Winona has to offer is within close proximity. Examples include: Coffee, restaurants, bars, 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 stay in beautiful Winona a memorable one!

4.97 out of 5 average rating, 154 reviews

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

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, 136 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, 154 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.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

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Convenient locations with everyday essentials

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Popular amenities for Winona vacation rentals

Laptop-friendly workspace

Vacation rentals with pools in Winona

4.97 out of 5 average rating, 29 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

4.87 out of 5 average rating, 179 reviews

Tiny home in La Crosse

Come unwind with us at Kindred Tiny House.

5 out of 5 average rating, 40 reviews

Two individuals are seated in a green float in the expansive pool, overlooking a vast landscape. The sun shines brightly above, casting reflections on the shimmering water, while rolling hills and trees extend into the distance.

Home in Rochester

RARE! Pool, hot tub, garden &chickens! 4m to Mayo

4.83 out of 5 average rating, 23 reviews

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

Cozy, quiet place w/pool/hot tub

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

4.79 out of 5 average rating, 14 reviews

The Shack

4.33 out of 5 average rating, 3 reviews

An inviting outdoor pool area features a large turquoise pool surrounded by well-maintained greenery and several lounge chairs. A spacious club house with large windows is visible in the background, set against a clear blue sky.

Condo in Rochester

Lovely 2 bedroom condo with nice amenities

4.99 out of 5 average rating, 75 reviews

A blue above-ground pool is surrounded by a wooden deck, with a ladder providing access. The back of the house is visible, featuring large windows and a spacious deck area. Lush greenery and a nearby umbrella enhance the outdoor setting.

Home in La Crosse

3BR 3BA w/ Pool & Hot Tub, near Goose Island

Camper/RV in Zumbro Falls

The Bunkhouse camper is positioned on a grassy area, featuring a covered outdoor space. Several patio chairs are arranged around a fire pit, providing a cozy setting. Trees and greenery are visible in the background, enhancing the natural surroundings.

4.93 out of 5 average rating, 15 reviews

Bunkhouse Camper - Bluff Valley Campground

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Apartment rentals in Winona

4.94 out of 5 average rating, 391 reviews

A green sofa sits centrally in a light-filled living area, flanked by two windows. A vintage map hangs above, adding a decorative touch. A round black table with a magazine and a woven basket are visible in the space, complemented by a patterned rug underfoot.

Apartment in Viroqua

Sunny & Historic 1 Bedroom Haven- Main St, Viroqua

4.93 out of 5 average rating, 254 reviews

A spacious sleeping area is framed by sliding barn doors, showcasing a soft white bed with a decorative pink throw. Two windows allow natural light to fill the room, illuminating the cozy reading nook with a chair and lamp nearby. A side table displays books and a candle.

Apartment in Wabasha

Beautiful Historic Apartment

A spacious living area features comfortable seating with a gray sofa and matching armchair adorned with textured throws. A wooden coffee table is centered on a decorative rug, while exposed brick walls and large arched windows add character and natural light to the space.

4.95 out of 5 average rating, 164 reviews

Spacious Loft in Downtown La Crosse

A welcoming living area is showcased, featuring a plush velvet couch in green, paired with two curved rattan chairs adorned with white cushions. A wooden coffee table sits centrally, and a unique pendant light hangs above, complemented by a floor lamp and natural light from the window.

5 out of 5 average rating, 153 reviews

Cozy 3BR by Mayo, Spacious Parking, 5 Steps

4.93 out of 5 average rating, 160 reviews

A cozy bedroom features a spacious bed with neatly arranged pillows and a navy throw blanket. Two lamps illuminate the nightstands flanking the bed. Wall art and a large mirror enhance the inviting atmosphere, while natural light filters in through nearby windows.

Apartment in Rochester

Home for the Traveler, a walk to St. Mary's

A charming A-frame house sits amidst greenery, showcasing wooden shingles and a steep roof. A patio area is visible, furnished with umbrellas and seating. Sunlight filters through the trees, illuminating the outdoor space, while garden flowers add a touch of color.

4.99 out of 5 average rating, 106 reviews

Amazing River Retreat with cozy shabby-chic design

4.98 out of 5 average rating, 107 reviews

Buddha’s Cloud

4.97 out of 5 average rating, 242 reviews

A cozy living room space features a beige couch adorned with decorative pillows and a low coffee table. The white brick wall serves as a backdrop for a fireplace, which is framed by a wooden mantle decorated with artwork and a wreath. Natural light enters through a window.

Apartment in Rochester

Restful sanctuary close to Mayo Clinic

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Apartment rentals with pools in Winona

A well-lit motel room features two spacious beds with white bedding. Light wood flooring complements the neutral wall color, while colorful artwork adorns the walls. A small kitchenette area with appliances is visible, along with a flat-screen TV mounted on a light wooden console.

4.86 out of 5 average rating, 22 reviews

Double Queen Room

A well-lit room features a spacious bed with crisp white linens. Two vibrant paintings adorn the wall above a small nightstand, and a blue retro mini-fridge adds a pop of color. A seating area with a blue chair is positioned near the window, enhancing the inviting space.

4.82 out of 5 average rating, 65 reviews

Single King Room

A well-lit motel room features a spacious bed with a textured white coverlet. Two bedside tables with lamps are positioned on each side. A round table sits near a small refrigerator, with a mirror and bathroom visible in the background.

4.63 out of 5 average rating, 8 reviews

Single Queen Room (main level)

An open living area showcases a gray sofa and a green chair, complemented by a round wood coffee table. Two framed artworks are displayed on the light-colored wall, while modern kitchen appliances are visible in the background, illuminated by soft natural light.

Apartment in Rochester

3.43 out of 5 average rating, 7 reviews

Two Bedroom Luxury in Rochester

The room features two spacious beds with light bedding, complemented by bedside tables. A television is mounted on the wall opposite, and modern decor accents the light-coloured walls. Large artwork adorns one wall, enhancing the welcoming ambience.