House holiday rentals in Winona

Find and book unique houses on Airbnb

Top-rated house rentals in Winona

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

%{current} / %{total}1 / 1
Top guest favourite
An aerial view of a spacious home surrounded by lush greenery and well-maintained grass. The property features multiple decks, providing outdoor spaces for relaxation. Mature trees add natural beauty to the landscape, enhancing the home's serene environment.
Home in Reads Landing
4.99 out of 5 average rating, 170 reviews

Gorgeous home overlooking the Mississippi River

Gorgeous, secluded home moments away from Wabasha. Free WiFi. Enjoy Septoberfest, one of the many terrific restaurants in the area, Music Under the Bridge, or any other fun activity this little river town has to offer. The house is fully furnished, with two bedrooms, but with room to sleep more. This is a one-of-a-kind property with a view that could only best be described by simply reading our reviews. Located south of Red Wing, between Lake City and Wabasha, in Reads Landing, Minnesota.

Top guest favourite
A spacious bed with a brass headboard is center-stage in the room, accented by layers of blue and white bedding. Nightstands with lamps are placed on either side, contributing to the overall balanced layout. Soft curtains frame a window, allowing natural light to fill the space.
Home in Minnesota City
4.97 out of 5 average rating, 311 reviews

✨Vintage Lustron Home✨

Enjoy a stay in this vintage Lustron Home. It is a unique home. It has two bedrooms, and a sofa sleeper in the living room. The master bedroom has a queen size bed. The second bedroom has two twin beds. This home offers a washer and dryer for your convenience. It has a large fenced yard to enjoy during your stay. Off street parking and Wi-Fi included. This home is in a very peaceful neighborhood. Located close to Winona State University and St. Mary's University. There are State Parks close also

Top guest favourite
A wooden tray is positioned on a neatly made bed, featuring a bottle of rose wine and two wine glasses. A small vase with a sprig of greenery adds a touch of freshness, complementing the subtle colors of the decorative pillows and bedspread.
Home in Galesville
4.95 out of 5 average rating, 111 reviews

Bright, spacious 3-bedroom farmhouse on 3 acres

Come stay in our recently updated 1800's farmhouse. Situated on 3 acres in a rural setting, this home is the perfect escape while still being centrally located among area attractions. Just 5 miles from the Mississippi, a state park and bike trail, a winery and an orchard, there is an abundance of nearby entertainment throughout the seasons. It is conveniently located between LaCrosse, WI and Winona, MN. WiFi and Roku available. There is ample off-street parking with space for trucks/trailers.

Guest favourite
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
4.95 out of 5 average rating, 149 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 favourite
A wooden sauna is positioned in the center of a rustic room with exposed beams and corrugated metal walls. Two wooden rocking chairs sit nearby. Light enters through several windows, and a basket is placed on the floor, enhancing the inviting, serene environment.
Home in Stockholm
4.96 out of 5 average rating, 276 reviews

Bogus Valley Holm Country/Farm Pepin/Stockholm

Come to the country and enjoy lodging at quiet Bogus Valley Holm. Located in picturesque Bogus Valley, between Pepin and Stockholm Wisconsin. This vintage home farmstead on 4 acres, was built in the mid 1850s and has old world character architecture with the comforts of modern day amenities. The southern exposure enclosed front porch is the favorite gathering spot for most everyone that has stayed in the home. This 2 bedroom 1 1/2 bath property has potential for sleeping up to 8 guests.

Top guest favourite
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, 193 reviews

Beautiful Views of the Mississippi river

Escape to a private Mississippi River retreat on 18 wooded acres. This spacious 6,300 sq ft home sits up high with stunning views of the river. It sleeps up to 14 with 5 bedrooms, 10 beds, and multiple living areas perfect for groups and gatherings. Enjoy a fully stocked kitchen with two fridges, complimentary coffee, laundry, a game room, games, and an outdoor fire pit. Peaceful, secluded, and designed for comfort—your ideal riverside getaway. No pets. Nearly 200 5-star reviews!!!

Top guest favourite
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, 178 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 favourite
A charming cabin is seen nestled among vibrant autumn foliage along the Mississippi River. The structure is surrounded by a mix of trees displaying warm seasonal colors, with a boat gently gliding across the river in the foreground.
Home in Winona
4.9 out of 5 average rating, 273 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 favourite
The living room features exposed brick walls and wooden beams overhead. A spacious couch is complemented by two chairs, while a coffee table sits atop an area rug. Natural light fills the space through large windows that offer views of the outdoor patio.
Home in Winona
4.98 out of 5 average rating, 239 reviews

~ 71 Johnson Street ~

This beautiful brownstone house is conveniently located in the heart of beautiful downtown Winona MN! It is within close proximity to many attractions Winona has to offer such as: Mississippi River front access, coffee shops, restaurants, bars & lounges, Winona State University, Lake Winona, hiking/biking trails, Shakespeare Festival, Minnesota Marine Art Museum, and much more! Please allow us to make your next stay in beautiful Winona a memorable one!

Top guest favourite
The exterior of the lodge is shown from a distance, with the building set on a slight hill. Two trees with vibrant autumn foliage flank the structure, and a covered deck extends along part of the front. A clear blue sky provides a contrasting backdrop.
Home in Arcadia
4.95 out of 5 average rating, 178 reviews

Sonney Lodge

Perched on a hilltop in scenic Newcomb Valley, Sonney Lodge provides a quiet, country setting while still only a 10 minute drive to downtown Arcadia. Located on a dead end with a private drive and no through traffic, the lodge features 3 bedrooms, 2 bathrooms, a full kitchen, dining room and lower level entertainment room. A covered deck wraps around 2 sides of the home offering spectacular views of the surrounding hills and countryside.

Top guest favourite
A vibrant room features colorful vinyl records displayed on the walls and a retro Janis Joplin concert poster. A mirrored dresser, adorned with unique lamps, reflects the eclectic decor, while a whimsical lava lamp adds a touch of playful charm.
Home in La Crosse
4.93 out of 5 average rating, 161 reviews

Nostalgic Retro Cottage-Faye's Place-Fully Fenced

Welcome to Faye's Place! We are a 2 bedroom/1 bath Cottage on the Northside of La Crosse with a full fenced in yard! We are right off of 1-90. 2 Blocks from The Black River! Close to Kwik Trip, Walgreens, Food and Animal Watching! 10 min. away from downtown and UWL! Faye's Place is my childhood home and is a small immersive experience. Themed rooms, nostalgic items, games, toys and a treasure hunt! We decorate for all holidays.

Top guest favourite
A spacious great room is featured, showcasing a wooden dining table with six chairs. A blue couch adorned with colorful cushions is positioned nearby. The kitchen area, equipped with modern appliances and a bar-style countertop, is highlighted by pendant lighting and plants.
Home in Winona
4.92 out of 5 average rating, 101 reviews

Craftsman's Home and Garden in Winona

Relax in a quiet family neighborhood surrounded by a unique garden and large backyard. The great room was designed for cooking and sharing meals with family and friends. Spill onto the front porch to enjoy the views of the bluffs and watch people stroll and bike past. Close to hiking and biking trails of Bluffside Park and St. Mary's University, and just a 15 minute scenic bike ride to the center of town.

Popular amenities for house rentals in Winona

When is the best time to visit Winona?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$204 SGD$162 SGD$200 SGD$200 SGD$211 SGD$214 SGD$208 SGD$210 SGD$209 SGD$210 SGD$203 SGD$222 SGD
Avg. temp-7°C-5°C2°C10°C16°C22°C24°C23°C18°C11°C3°C-4°C

Quick stats about house rentals in Winona

  • Total holiday rentals

    Explore 30 holiday rentals in Winona

  • Nightly prices starting at

    Winona holiday rentals start at $25 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,130 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Winona holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winona rentals

  • 4.9 Average rating

    Winona stays are highly rated by guests – averaging 4.9 out of 5!

  1. Airbnb
  2. United States
  3. Minnesota
  4. Winona County
  5. Winona
  6. House rentals