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Vacation rentals in Winona

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Top-rated vacation rentals in Winona

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

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Top guest favorite

An open kitchen and living space feature a large wooden countertop with three metal stools. The room is illuminated by a stylish chandelier, with a brick accent wall providing character. Large windows allow natural light to fill the area, showcasing the hardwood floors.

4.99 out of 5 average rating, 731 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

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, 198 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.

Top 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, 248 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

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, 290 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!

A serene view of the Mississippi River is captured, featuring a boat and a paddleboarder on calm waters. Lush green trees line the riverbanks, while gentle hills rise in the background under a cloudy sky.

Home in Fountain City

4.96 out of 5 average rating, 137 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

A rustic cabin constructed from logs is surrounded by snow-covered ground, featuring a welcoming porch with wooden railings. Red chairs are positioned on the porch, inviting relaxation. The entrance is framed by landscaped bushes, harmonizing with the natural winter scenery.

Cabin in Dakota

4.91 out of 5 average rating, 223 reviews

Secluded cabin in beautiful river valley.

Cozy Cabin in the woods! You can go hiking, cross country skiing, snow showing, bird watching, 5 minutes from the Mississippi River, local shopping in LaCrosse, Wi. and Winona, Mn. Or just simply sitting around the campfire and enjoying the peace and quiet of nature. Great River Bluffs Mn state park is widely known for cross county, and hiking trails! Beautiful views of the Mississippi! Located within minutes. You can enjoy outside dining with our gas grill. Fire wood is available.

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, 130 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, 146 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.

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.

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.

Vacation rentals for every style

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Popular amenities for Winona vacation rentals

Laptop-friendly workspace

Air conditioning

Other great vacation rentals in Winona

Private room in Stockton

4.81 out of 5 average rating, 129 reviews

Peaceful Country Charm

Top guest favorite

Guest suite in Coon Valley

4.97 out of 5 average rating, 70 reviews

Loghome Studio/10 Min to La Crosse-Wk/Mo Discounts

Top guest favorite

The exterior of the converted Video Vision building is visible, showcasing a modern architectural design. Surrounding greenery and nearby hills enhance the setting. A historic sign featuring the name 'Video Vision' is prominently displayed in front of the property, indicating its past use.

Hotel room in Winona

4.94 out of 5 average rating, 139 reviews

Alien Robot room 2078 at Video Vision

Top guest favorite

The renovated barn features a red exterior with a metal roof, framed by green trees. A sunset casts a warm glow over the property, enhancing its rural charm. Nearby structures, including a small outbuilding, add to the idyllic setting.

4.93 out of 5 average rating, 58 reviews

Scrappin' on the Ranch

Top guest favorite

The living room features wood flooring and a vibrant area rug that adds warmth to the space. A combination of black leather sofas, a tufted ottoman, and wooden chairs provide ample seating. Natural light flows through sheer curtains, illuminating a round marble coffee table and wall art.

5 out of 5 average rating, 8 reviews

Turquoise Bear: Driftless Lake Retreat

Top guest favorite

A charming cottage exterior is visible, featuring a welcoming deck with an umbrella and steps leading to the entrance. Lush greenery and a wooden path line the front, which enhances the natural surroundings of the home.

Cabin in Winona

5 out of 5 average rating, 14 reviews

Esther’s Cottage

A spacious exterior view of the house is presented, surrounded by well-maintained green lawns and landscaping. Trees provide shade while the blue sky adds brightness to the scene. The inviting porch can be seen, enhancing outdoor accessibility.

Private room in Trempealeau

4.83 out of 5 average rating, 198 reviews

Patty & Mike's Basement Level-close to Perrot Park

Top guest favorite

The entrance features a welcoming front porch with a dark door framed by large windows. A comfortable bench offers seating next to potted flowers, contributing to a serene atmosphere. The house exterior is finished in dark siding, complemented by a light brown overhang.

5 out of 5 average rating, 16 reviews

Parkside Pet Friendly Bungalow

Quick stats about vacation rentals in Winona

Total rentals
80 properties
Nightly prices starting at
ﺩ.ﺇ73 before taxes and fees
Total number of reviews
9.2K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Winona?
Yes! Work meets play with ease at over 30 vacation rentals in Winona featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Winona?
Four-legged friends are welcome in Winona. Choose from more than 10 vacation rentals for guests traveling with pets.
Do apartment rentals in Winona have air conditioning?
Absolutely! We offer over 20 apartment rentals with air conditioning in Winona. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winona have wifi?
Absolutely! We offer over 30 house rentals with wifi in Winona. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Winona?
Winona has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Winona have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Winona. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Winona?
Experience the best of Winona with our apartment rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for Apartment Rentals in Winona?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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