
House vacation rentals in Winona
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Top-rated house rentals in Winona
Guests agree: these houses are highly rated for location, cleanliness, and more.

BikeProfessor's Bungalow, near trails and downtown
Charming home with hardwood floors, leaded glass windows, and original details in the faculty neighborhood close to UW-L campus and Downtown. Are you visiting La Crosse to paddle, fish, hike, bike, or ski? With bluff views, the Bicycle Professor's Bungalow is close to it all. My home is a ten minute walk to the marvelous Marsh Trail system that links the University to Downtown. I will happily offer tips for restaurants, walks, bicycle rides and places to ski. The Driftless terrain is endless!

✨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

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.

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.

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.

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.

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!

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.

~ 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!

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.

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.

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
House rentals with a pool

The Shack

Walkable Retreat in a Historic Neighborhood

3BR 3BA w/ Hot Tub, near LaX' Top Rated Activities

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

A-Frame Pool House Hot Tub / POOL/ Sleeps 6

Indoor pool-Arcades-Amazing Views!

Secluded Home With Unbeatable Views & Heated Pool

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

The North Farm Hillside Retreat

Paradise Valley Sanctuary + Starlink Internet

Ridgeview Retreat 11244 Davy Road Hokah, MN 55941

House on the Water

The Cottage

River View - Fun Stay - Walking Distance to Bars

Dock on the Mighty Mississippi!

4bd River Retreat, Nearby Skiing & Rotary Lights!
Private house rentals

Historic Mobile Inn

Root River Cozy Cottage

Riverview, 5BR, Hot tub, Fireplace, Arcade Game

Comfortably Lost

HOUSE ON THE RIVER

Convenient, Family friendly!

Charming home with views of the Mississippi River

Arcadia Cottage
When is the best time to visit Winona?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ588 | ﺩ.ﺇ466 | ﺩ.ﺇ577 | ﺩ.ﺇ577 | ﺩ.ﺇ610 | ﺩ.ﺇ617 | ﺩ.ﺇ599 | ﺩ.ﺇ606 | ﺩ.ﺇ602 | ﺩ.ﺇ558 | ﺩ.ﺇ595 | ﺩ.ﺇ580 |
| Avg. temp | -7°C | -5°C | 2°C | 10°C | 16°C | 22°C | 24°C | 23°C | 18°C | 11°C | 3°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 ﺩ.ﺇ73 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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