Holiday rentals in Winona

4.99 out of 5 average rating, 708 reviews

Loft in Winona

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

4.95 out of 5 average rating, 229 reviews

Flat in Winona

2nd Floor Retreat - 7 Blocks from WSU

Our one-bedroom apartment is perfect for two guests. * NO cleaning fee/deposit required * Spacious bedroom with queen size bed, couch and workspace * Fully kitchen with oven, refrigerator, microwave + coffee/tea station * TV, board games and books * All amenities needed 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.

4.99 out of 5 average rating, 223 reviews

Bungalow in Winona

*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!

4.92 out of 5 average rating, 266 reviews

Farm stay in Dakota

The Cottage at The Healing Refuge

Welcome to The Healing Refuge! Come experience life on a Minnesota farm nestled in the rolling hills of the Driftless area! Relax outside on the deck, swing in a hammock among the trees, or walk through our beautiful cover crop fields. This is a working farm & depending on the season, you are welcome to help collect eggs, chat with the horses, observe the numerous farm animals, or learn about regenerative farming. We want your experience at our farm to be relaxing and refreshing!

4.95 out of 5 average rating, 130 reviews

Home in Fountain City

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.

4.98 out of 5 average rating, 129 reviews

Home in Fountain City

Bluffside cottage with gorgeous river 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.

4.94 out of 5 average rating, 84 reviews

Flat in Winona

Treetops Suite, 1 Bedroom @ 7th Street Retreat

Treetops for 2 is located in the heart of Winona. The upstairs apartment has a secure, self check-in entrance located at the back of the house, has 1 BR (double bed), bathroom (shower), kitchenette and living area. It has a remote controlled heating/cooling system, cable and internet-enabled TV/DVD, and Wi-Fi. Guests share the driveway, back entrance, laundry room, and back patio. The steps up to the apartment are steep. The space is 3 blocks from a charging station.

4.91 out of 5 average rating, 246 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.

4.97 out of 5 average rating, 156 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. We have one outdoor security camera. Sorry, No pets.

4.96 out of 5 average rating, 137 reviews

Tiny home in Winona

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.

4.93 out of 5 average rating, 170 reviews

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.

4.99 out of 5 average rating, 156 reviews

Loft in Arcadia

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.

Holiday rentals for every style

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Flats

Convenient locations with everyday essentials

Popular amenities for Winona holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Winona

Private room in La Crosse

4.94 out of 5 average rating, 203 reviews

SuperHost Safe & Clean, great location

KiraRating, 5 stars1 week ago

Host was really kind and flexible with my check in time. Had a cute basket of towels and soap for me, the space was clean and she had great local recommendations.

4.81 out of 5 average rating, 120 reviews

Private room in Stockton

Peaceful Country Charm

AshleeRating, 5 stars1 day ago

Stayed at Tammy’s the night before a bike race in Winona. Honestly bummed that we didn’t get to spend more time there. They have a beautiful property. Tammy and her husband are super nice, friendly and welcoming. They will make you feel right at home. Before a bike race I am always anxious about getting good sleep, I didn’t have to worry about that at Tammy’s at all! The in-room microwave and fridge is super nice.

4.94 out of 5 average rating, 53 reviews

Farm stay in Winona

Irish Ridge Farm Guest House: Rural Winona Co

CarrieRating, 5 stars2 weeks ago

A perfect location for a weekend getaway with four adults and four kids. The location was ideal - peaceful, beautiful, and lots of fun animals! It was close enough to Winona that it was easy to go into town for exploring and food. Maggie was also incredibly helpful and responsive.

4.93 out of 5 average rating, 60 reviews

Home in Fountain City

Our Little River House

KatieRating, 5 stars1 week ago

This was the perfect little gem!! House had a beautiful view of the river and bluffs, right in the heart of Fountain City. The house was super clean, had everything we needed, and the added bonus was that the floors must have been very well insulated because putting our babies to bed upstairs, you couldn’t hear anything happening downstairs! There was a private back yard for our dog to run around in as well which was perfect. Would definitely recommend and I hope to return!

4.95 out of 5 average rating, 113 reviews

Hotel room in Winona

Alien Robot room 2078 at Video Vision

MicheleRating, 5 starstoday

The room was perfect for us! The first night there we went to the restaurant right across from it, then we wandered over for some cosmic bowling. The bed was comfy, the shower was amazing and the value is unmatched.

5 out of 5 average rating, 14 reviews

Waterfront | HOT TUB | Sleeps 15

BriannaRating, 5 stars3 months ago

This is a great spot located between Winona and La Crosse with so many things to do! The Airbnb is located right next to railroad tracks but the host does provide earplugs to help with the noise. The directions were very clear to get to the home. The home was very clean and aesthetic! The host provided many board games and the house had lots to do for a quiet night in. Definitely would come back!