
House vacation rentals in Winona
Find and book unique houses on Airbnb
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 G$4,185 GYD per night before taxes and fees

Verified guest reviews
Over 2,210 verified reviews to help you choose

Family-friendly vacation rentals
20 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!
Top-rated house rentals in Winona
Guests agree: these houses are highly rated for location, cleanliness, and more.

✨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

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.

Stunning Views! - Sugarloaf @HighPointRetreats
Perched in the solitude of nature, our ridge top retreat offers a picturesque view at one of the top elevations in all La Crosse County. Cozy up to your loved ones, relax with friends, or find inspiration in this one-of-a-kind private duplex. Sugarloaf is named after Sugarloaf Summit located 17 miles west of the retreat. Sugarloaf sleeps 4-5 and is non-smoking. Get your front row sunset seats on the private patio and relax in the soaker tub. Immerse yourself in tranquility and come stay us.

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.

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!!!

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.

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!

Bogus Valley Holm Country/Farm Pepin/Stockholm
Come to the country and enjoy lodging at our Bogus Valley Holm. Located in picturesque Bogus Valley, between Pepin and Stockholm Wisconsin. Just a short drive to the area wedding venues and other West Coast Wisconsin attractions. 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. If you are looking for a quiet rural getaway, this is your place.

Waterfront A-Frame on the Marina • Lake Pepin
A classic A-frame on the marina, where the Mississippi widens into a lake three miles across and the bluffs rise on both sides. Steps from Harbor View Café and The Pickle Factory, close to Villa Bellezza and Woods & Co. — one of the best-positioned spots in Pepin for a wedding weekend, a romantic escape, or a few days of doing exactly nothing. You have the best views, and you can walk everywhere Best location in town.

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.

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.
Popular amenities for Winona house rentals
House rentals with a pool

Bear Creek Lodge w/ Pool and Hot Tub

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

3 Bedroom home (sleeps 8)

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

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

Backyard Oasis w/ In-Ground Pool, FirePit & Gazebo

The Shack

Walkable Retreat in a Historic Neighborhood
Weekly house rentals

SG BrickHouse

Haven on Huff

The Sierra! Close to Mayo Clinic

*Monthly Rates Available* A cozy, rustic home.

Nostalgic Retro Cottage-Faye's Place-Fully Fenced

The Guest House

Secluded Rustic Rose Cabin

Sonney Lodge
Private house rentals

Our Little River House

Historic Mobile Inn

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

Convenient, Family friendly!

Mississippian River Cabin

The Driftless House - Winona, MN

River View - Fun Stay - Walking Distance to Bars

The Village House Inn
When is the best time to visit Winona?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$35,572 GYD | G$33,061 GYD | G$29,086 GYD | G$32,852 GYD | G$34,735 GYD | G$35,154 GYD | G$34,108 GYD | G$34,526 GYD | G$34,317 GYD | G$34,526 GYD | G$33,271 GYD | G$36,409 GYD |
| 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 |
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