Holiday rentals in Winona

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Top-rated holiday rentals in Winona

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Guest favourite

Home in Minnesota City

4.98 out of 5 average rating, 272 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

18–25 Sept

£102 per night

Guest favourite

Farm stay in Dakota

4.93 out of 5 average rating, 247 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!

17–24 Feb

£82 per night

Guest favourite

Flat in Winona

4.94 out of 5 average rating, 140 reviews

Cozy & Bright 2nd Floor Apt - 7 Blocks from WSU

Our newly-remodeled one-bedroom apartment is the perfect getaway for two guests. * Spacious bedroom with queen size bed, couch and workspace * Hardwood floors throughout * Full kitchen with oven, refrigerator, microwave + coffee/tea station * Walking distance to WSU and Cotter * Located on the 2nd floor with off-street parking * 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.

4–11 Oct

£86 per night

Guest favourite

Bungalow in Winona

4.99 out of 5 average rating, 158 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!

22–29 Dec

£228 per night

Guest favourite

Cottage in Winona

5.0 out of 5 average rating, 45 reviews

Cozy Casita by the Lake

Come stay at our relaxing casita with an unbeatable location near beautiful Lake Winona! On a dead-end street, the house is steps from Lake Winona and access to its walking paths and park. It's just two blocks to Winona State and a mile to downtown. Our home has historic charm, comfortable furnishings, a fully updated kitchen, and reliable wifi. With two bedrooms, this cozy house is a perfect home base for your trip to Winona. Well-behaved dogs are welcome at no extra cost.

11–18 Oct

£132 per night

Guest favourite

Home in Winona

4.91 out of 5 average rating, 206 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.

14–21 Mar

£119 per night

Guest favourite

Home in Winona

5.0 out of 5 average rating, 14 reviews

The Little Train Depot

The Little Train Depot is a comfortable space for you to relax while visiting the quaint river town of Winona. There are a number of things to do in the area including; the Midwest Music Festival, Great River Shakespeare Festival, Frozen River Film Festival, boating on the Mississippi, visiting our local museums or vineyards, enjoy the unique Lark Toys, shops with local artisans, visiting our weekly farmers market or just relax by the lakes.

29 Aug – 5 Sept

£81 per night

Guest favourite

Flat in Winona

4.98 out of 5 average rating, 817 reviews

~ Third Street Suites ~ #11

Hi! This beautiful main level apartment is conveniently located in the heart of downtown Winona MN! Everything Winona has to offer is within close proximity. Examples include: 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 stay in beautiful Winona a memorable one!

9–16 Nov

£94 per night

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.

9–16 Oct

£147 per night

Guest favourite

Home in Winona

4.96 out of 5 average rating, 110 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.

3–10 Jan

£349 per night

Guest favourite

Loft in Arcadia

4.98 out of 5 average rating, 121 reviews

Tamarack Point Homestead

Tamarack Point Homestead is located between Arcadia, WI and Centerville, WI in the beautiful valley of Tamarack. This scenic 150 year old homestead has an outbuilding loft that allows you to enjoy the country lifestyle and experience the best that Trempealeau County has to offer. Certified to operate by the Trempealeau County Health Department.

16–23 Jul

£84 per night

Guest favourite

Flat in Winona

4.95 out of 5 average rating, 19 reviews

NOVA Treehouse

This peaceful, country getaway is perfectly centered between La Crosse and Winona(15 mins to either city). We are a working homestead with 14 acres of space to explore. Rustic and wild on the outside and stylish and comfortable on the inside. We welcome families and are happy to share our jungle-gym and swing set with children who stay with us.

28 Nov – 5 Dec

£76 per night