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Vacation rentals in Winona

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Top-rated vacation rentals in Winona

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Home in Minnesota City

4.98 out of 5 average rating, 285 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

Tiny home in Black River Falls

4.97 out of 5 average rating, 358 reviews

Tiny on the River

According to Forbes, Escape makes "the most beautiful tiny houses in the world". Ours is perched near our home above the Black River. It's a quiet neighborhood just minutes from the interstate, parks, trails, and our vibrant downtown with cafés, shops, and great restaurants. Enjoy privacy and breathtaking views from the enormous windows or the cozy daybed on the porch! Deer, beaver, eagles, and more make frequent cameos as the seasons paint shifting riverscapes and astonishing sunsets. *No Pets

Rental unit in Winona

5 out of 5 average rating, 150 reviews

~ Third Street Suites ~ #7

This beautiful 3rd story- 2 level penthouse apartment (ACCESSED BY STAIRS ONLY UP TO 3RD LEVEL ) is conveniently located in the heart of downtown Winona MN! Everything Winona and the downtown area has to offer is within close proximity. Examples include: Coffee, restaurants, bars, brewery, Winona State University, Mississippi , 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!

Bungalow in Winona

4.99 out of 5 average rating, 177 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!

Cottage in La Crosse

4.89 out of 5 average rating, 273 reviews

Sunsets on the Edge

My place is 10 minutes from downtown La Crosse, close to the airport, but you'll feel a world away. You’ll love my place because of the peace and quiet, but mostly THE VIEWS. All the modern conveniences of dishwasher, microwave, shower and stove/fridge, washer & dryer. You'll never see the same sunset! My place is good for couples, solo adventurers. Full list of amenities available, but worth noting here that coffee is NOT provided. There is a drip coffee maker, as well as a Keurig for pods.

Rental unit in Winona

4.95 out of 5 average rating, 171 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.

Home in Fountain City

4.95 out of 5 average rating, 109 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.

Home in Winona

4.9 out of 5 average rating, 213 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.

Home in Winona

4.97 out of 5 average rating, 124 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.

Tiny home in Winona

4.95 out of 5 average rating, 129 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.

Home in Winona

4.94 out of 5 average rating, 132 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.

Loft in Arcadia

4.98 out of 5 average rating, 130 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.

Vacation rentals for every style

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Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Winona vacation rentals

Free parking on premises

Air conditioning

Stay near Winona's top sights

Minnesota Marine Art Museum32 locals recommend

Garvin Heights Lookout17 locals recommend

Island City Brewing Company Co15 locals recommend

Blue Heron Coffeehouse15 locals recommend

Acoustic Cafe15 locals recommend

The Boat House Restaurant14 locals recommend

Other great vacation rentals in Winona

Home in Winona

4.95 out of 5 average rating, 73 reviews

A Stone's Throw Bungalow

Rental unit in Rollingstone

5 out of 5 average rating, 10 reviews

Entire cozy Rollingstone apt. 10 min to Winona!

Home in Fountain City

5 out of 5 average rating, 18 reviews

Fountain City Loft, hot tub, river views

Home in Fountain City

4.98 out of 5 average rating, 83 reviews

Bluffside cottage with gorgeous river views

Home in Winona

4.98 out of 5 average rating, 62 reviews

Ellie’s Place

Tiny home in La Crosse

4.96 out of 5 average rating, 82 reviews

Come unwind with us at Kindred Tiny House.

Home in Galesville

4.9 out of 5 average rating, 62 reviews

Bright, spacious 3-bedroom farmhouse on 3 acres

Tiny home in Dakota

4.75 out of 5 average rating, 12 reviews

Ridgetop Retreat

Quick stats about vacation rentals in Winona

Total rentals
70 properties
Nightly prices starting at
$20 before taxes and fees
Total number of reviews
7K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Winona?
Yes! Work meets play with ease at over 30 vacation rentals in Winona featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Winona?
Four-legged friends are welcome in Winona. Choose from more than 10 vacation rentals for guests traveling with pets.
Do apartment rentals in Winona have air conditioning?
Absolutely! We offer over 20 apartment rentals with air conditioning in Winona. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winona have wifi?
Absolutely! We offer over 20 house rentals with wifi in Winona. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Winona?
Winona has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Winona have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Winona. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Winona?
Experience the best of Winona with our apartment rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Winona?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a bbq area, over 20 homes with wifi, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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