House vacation rentals in Winona

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Top-rated house rentals in Winona

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Top guest favorite
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
4.98 out of 5 average rating, 306 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 favorite
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
4.94 out of 5 average rating, 103 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.

Top guest favorite
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, 146 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.

Guest favorite
An open living area is highlighted by a spiral staircase leading to a loft. Large windows provide natural light and views of the waterfront. A cozy seating arrangement features a stylish couch and armchair on a patterned rug, complemented by a modern entertainment unit.
Home in Pepin
4.91 out of 5 average rating, 194 reviews

Waterfront A-Frame w/ Perfect View of Lake Pepin!

Welcome to The Dockside A-Frame Cabin! The prime spot in Pepin, you are right on the waterfront in a stylish A-Frame home with a balcony and sweeping Lake Pepin views. Wake up with coffee to a river view. Walk to dinner at the famed Harbor View Cafe, then enjoy a glass of local wine at Rivertime Wine Bar or Villa Bellezza winery. End your evenings on the balcony, watching the sunset. This is one of two units on the Dockside property! See my Host Profile for the other listing.

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
4.98 out of 5 average rating, 166 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.

Top guest favorite
Home in La Crosse
4.92 out of 5 average rating, 138 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. Ask about our Dive Bar Tour!

Guest favorite
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, 262 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
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, 216 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 favorite
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, 172 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 favorite
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, 184 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.

Top guest favorite
The exterior of a renovated two-story home is shown, featuring light grey siding and a welcoming aqua front door. A concrete pathway leads to the entrance, complemented by neatly landscaped grass and plant beds. An oversized window allows natural light into the upper level.
Home in Winona
4.99 out of 5 average rating, 113 reviews

Ellie’s Place

This historic Winona home has gone through a complete renovation to make your stay enjoyable. It is in close proximity to many of the attractions that make Winona special: hiking/biking trails, Winona State University, Mississippi River, coffee shops, restaurants, bars, Lake Winona, Saint Mary’s University, Minnesota Marine Art Museum, music festivals, the winter ice wall and so much more.

Top guest favorite
A charming house is depicted with dark grey siding and a steeply pitched roof. Large windows provide ample natural light, framed by white trim. A white front door serves as the focal point, flanked by lantern-style lights. Flower pots enhance the welcoming entrance.
Home in Winona
4.93 out of 5 average rating, 192 reviews

Spacious Retreat for 1-8 guests

Staying with us for work or pleasure, this tranquil home is sure to suit all your needs. It has been renovated with charm and comfort in mind. All the modern indoor amenities will make you feel at home. Outdoors, enjoy the fully fenced in yard for privacy. It is conveniently located near Winona’s outdoor recreation, shopping, hospital and more.

Popular amenities for Winona house rentals

When is the best time to visit Winona?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR2,718 ZARR2,158 ZARR2,667 ZARR2,667 ZARR2,820 ZARR2,854 ZARR2,769 ZARR2,803 ZARR2,786 ZARR2,582 ZARR2,752 ZARR2,684 ZAR
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 vacation rentals

    Explore 30 vacation rentals in Winona

  • Nightly prices starting at

    Winona vacation rentals start at R340 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 2,040 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Winona vacation rentals include wi-fi 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!

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