Holiday houses in Winona County

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Top-rated holiday rentals in Winona County

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Guest favourite

Farm stay in Dakota

4.93 out of 5 average rating, 249 reviews

The Bungalow at Heart and Soil Ridge

Welcome to Heart and Soil Ridge! Come experience life on a Minnesota farm nestled in the rolling hills of the Driftless region. Relax out on the deck, swing in a hammock among the trees, or enjoy a walk through our beautiful cover crop fields. This is a working farm and depending on the season, you are welcome to help collect eggs, observe the farm animals, learn about regenerative agriculture, and visit our Fox Red labradors. We want your experience at our farm to be relaxing and refreshing!

Guest favourite

Home in Minnesota City

4.97 out of 5 average rating, 277 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

Guest favourite

Home in Rushford

4.89 out of 5 average rating, 175 reviews

Country Cottage in SE Minnesota Bluff Country

Experience the beauty SE Minnesota and 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 non-smoking space that involves (three) stairs to access the first floor. Limited cell reception.*

Guest favourite

Loft in Winona

4.99 out of 5 average rating, 582 reviews

Penthouse Retreat-Near Downtown Winona!

Hi! This beautiful loft is conveniently located in the heart of Winona MN! Only a few blocks from the downtown and in close proximity to many other attractions Winona has to offer such as: Coffee, restaurants, a wine bar, Winona State University, Mississippi River, Lake Winona, hiking trails, Shakespeare Festival, Minnesota Marine Art Museum, and much more! Please allow us to make your next extended stay in beautiful Winona a memorable one! * MUST CLIMB STAIRS TO UNIT- LOCATED ON THE 3RD LEVEL

Guest favourite

Bungalow in Winona

4.99 out of 5 average rating, 162 reviews

*Prairie Island Bungalow with Water Access*

Welcome to Prairie Island Bungalow (PIB)! Located on Prairie Island in Winona, this home provides the perfect, quiet getaway for work or play, and is your gateway to outdoor adventure in the Winona area. River access is available on our private dock next door! With thoughtful amenities including a fully-stocked kitchen (with coffee and tea!), plush linens, Smart TVs, games and books, a fire pit, snowshoes, and kayak and canoe rentals; we invite you to simply show up and enjoy your stay at PIB!

Guest favourite

Apartment in Winona

4.94 out of 5 average rating, 145 reviews

2nd Floor Retreat - 7 Blocks from WSU

Our one-bedroom apartment is the perfect for two guests. * Spacious bedroom with queen size bed, couch and workspace * Fully stocked kitchen with oven, refrigerator, microwave + coffee/tea station * TV with Netflix, board games and books * All the amenities you need for a comfortable stay * Walking distance to WSU and Cotter * Your own washer dryer in the apartment * Easy self-check-in process We want you to love your time in Winona and are here to make your stay as pleasant as possible.

Guest favourite

Home in Fountain City

4.95 out of 5 average rating, 101 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 favourite

Farm stay in Trempealeau

4.96 out of 5 average rating, 103 reviews

Frank’s Farmhouse at Ecker’s Apple Farm

No Pets, please! Franks' Farmhouse is on the corner acreage of our family orchard, Ecker's Apple Farm. Winters, springs, and summers are peaceful and quiet at the farm. Take your morning coffee on a walk through our apple trees. The house is in close proximity to our orchard market and beer garden which is open late August through November. Frank's Farmhouse is small and quaint. We must emphasize that Frank's holds 6 people, maximum. Children count as people.

Guest favourite

Apartment in Trempealeau

4.97 out of 5 average rating, 102 reviews

Small Town Vibes with Amazing River & Bluff Views

Enjoy gorgeous view of the Mississippi River and bluffs, entertain yourself with the live music (occasionally late) from neighboring establishments, stargaze on the deck, or revel in the passing trains. This apartment is the perfect place to get away and relax. Bring up your boat as you'll have parking available in the driveway too! NOTE: this is an upstairs apartment, but we promise you won't be disappointed and want to come back again and again. NON SMOKING.

Guest favourite

Home in Winona

4.91 out of 5 average rating, 207 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.

Guest favourite

Tiny home in Winona

4.99 out of 5 average rating, 118 reviews

Potluck String Lodge (PSL)

Potluck String Lodge (PSL) is situated within Prairie Island Campground along the Mississippi River. With cottony sheets, coffee & towels, paddle sport equipment & bikes, and an outdoor fire ring, you can simply show-up, relax, reconnect, and recreate. This tiny house tells a story about the Boats and Bluegrass music festival and one of the campground picking circles hosted by the Potluck String Band.

Guest favourite

Home in Winona

4.96 out of 5 average rating, 112 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. Sorry, No pets.