
House holiday 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.

✨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.

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.

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 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.

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!

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.

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 house rentals in Winona
House rentals with a pool

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

The Shack

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

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

Indoor pool-Arcades-Amazing Views!
Weekly house rentals

Our Little River House

Haven on Huff

The Driftless House - Winona, MN

Turquoise Bear: Driftless Lake Retreat

Dock on the Mighty Mississippi!

Secluded Modern Farmhouse

The Village House Inn

The Little Train Depot
Private house rentals

Riverview Radiance: 5BR, Scenic Views, Pets OK

Marigold

Daddy Roy's Bed & Vintage

Pleasant Corner Schoolhouse

Waterfront | HOT TUB | Sleeps 15

The Cottage

River views, cozy, & decorated for the Holidays!

Beautiful Cozy Lake House on 2 & 1/2 acres!
Quick stats about house rentals in Winona
Total rentals
30 properties
Nightly prices starting at
£15 before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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