Winona vacation rentals

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Top-rated vacation rentals in Winona

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

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Guest favorite

Tiny home in Black River Falls

4.98 out of 5 average rating, 344 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

Guest favorite

Home in Minnesota City

4.97 out of 5 average rating, 279 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 favorite

Farm stay in Dakota

4.93 out of 5 average rating, 250 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 favorite

Cottage in Rushford

4.97 out of 5 average rating, 173 reviews

Relax, Recharge and Reconnect at The Hiding Place!

Nestled in the beautiful bluff country of SE Mn. THE HIDING PLACE COTTAGE is the perfect retreat when you want to relax, reconnect & recharge! This private cottage sits on a 43 acre property, has a King sz. bed, fireplace, kitchenette, large deck, fire pit and more! Enjoy the onsite wooded hiking trails, golf across the highway at Ferndale Golf Club, enjoy the SE Mn. biking trail or tube/canoe/kayak the Root River- both only 2 miles away. Snowmobilers-jump right on the trail from the property!

Guest favorite

Loft in Winona

4.99 out of 5 average rating, 586 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 favorite

Bungalow in Winona

4.99 out of 5 average rating, 163 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 favorite

Cabin in Spring Grove

4.98 out of 5 average rating, 407 reviews

Modern Country Cabin

Clear your mind at this modern, fully furnished cabin in heart of the Driftless region of MN, WI, and IA. Built in 2016, this truly unique space has everything you need for a relaxing getaway. There is plenty of space inside the cabin. The cabin contains two private rooms, one with a king size bed and the other with a queen bed. In the summer months there is also opportunity to camp, with 4 acres of luscious green space + some woodlands! Indoor fireplace, outdoor fire pit, and Traeger grill!

Guest favorite

Apartment in Winona

4.94 out of 5 average rating, 151 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 favorite

Home in Winona

4.91 out of 5 average rating, 208 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 favorite

Tiny home in Winona

4.98 out of 5 average rating, 120 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 favorite

Guesthouse in Viroqua

4.98 out of 5 average rating, 126 reviews

stylish guesthouse minutes from viroqua

Experience for yourself everything the Driftless has to offer during your stay in this stylish, timber-framed, eco-friendly guesthouse on our 8-acre rural retreat. Completed in 2021, you'll love this bright, clean, private, and peaceful space. Fish nearby trout streams, go for a bike ride, explore great state and county parks, or shop and dine in Viroqua (7 miles away) and Westby (3 miles).

Guest favorite

Loft in Arcadia

4.98 out of 5 average rating, 123 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

Get the amount of space that is right for you

Popular amenities for Winona vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Winona's top sights

Prairie Island Campground3 locals recommend

Hy-Vee5 locals recommend

Bloedow's Bakery13 locals recommend

Bub's Brewing Co7 locals recommend

Acoustic Cafe15 locals recommend

Midtown Foods5 locals recommend

Other great vacation rentals in Winona

Guest favorite

Cabin in Mindoro

4.96 out of 5 average rating, 186 reviews

Stunning Views! - Bunker Hill @HighPointRetreats

Guest favorite

Cottage in La Crosse

4.89 out of 5 average rating, 138 reviews

Cheerful Cottage Near the Bay

Guest favorite

Cottage in Pepin

4.97 out of 5 average rating, 401 reviews

Lost Creek Retreat

Guest favorite

Apartment in Trempealeau

4.97 out of 5 average rating, 103 reviews

Small Town Vibes with Amazing River & Bluff Views

Guest favorite

Loft in La Crosse

5.0 out of 5 average rating, 104 reviews

Luxury downtown loft with parking

Guest favorite

Home in Fountain City

4.95 out of 5 average rating, 101 reviews

River Road Abode: breathtaking river views

Guest favorite

Cottage in La Crosse

4.88 out of 5 average rating, 269 reviews

Sunsets on the Edge

Guest favorite

Cottage in Stoddard

4.92 out of 5 average rating, 166 reviews

Stylish 1 bedroom cottage on the Mississippi River

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Other great vacation rentals in Winona

Guest favorite

Apartment in Winona

4.95 out of 5 average rating, 21 reviews

NOVA Treehouse

Guest favorite

Cottage in Winona

4.91 out of 5 average rating, 23 reviews

Quiet Cottage in the Valley with Sauna

Superhost

Apartment in Winona

4.89 out of 5 average rating, 19 reviews

The Exchange 14 | Historic Bldg, Studio, Dwntwn

Guest favorite

Home in Winona

5.0 out of 5 average rating, 25 reviews

Relaxing Stylish Home

Guest favorite

Home in Lewiston

4.99 out of 5 average rating, 92 reviews

Rolling Ridge Retreat

Guest favorite

Guest suite in Fountain City

4.98 out of 5 average rating, 42 reviews

Backwaters Bungalow: waterfront/next to state park

Guest favorite

Farm stay in Wykoff

4.9 out of 5 average rating, 30 reviews

Bin There, Done That (and Pickleball too!)

Guest favorite

Vacation home in La Crosse

5.0 out of 5 average rating, 34 reviews

The Redhouse

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Quick stats about vacation rentals in Winona

Total rentals
70 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
6.4K reviews
Nightly prices starting at
$20 before taxes and fees

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 20 vacation rentals for guests traveling with pets.
Do apartment rentals in Winona have air conditioning?
Absolutely! We offer over 30 apartment rentals with air conditioning in Winona. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Winona have wifi?
Absolutely! We offer over 30 apartment 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 house rentals in Winona?
Experience the best of Winona with our house rentals, starting at about $20 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 20 homes with wifi, over 20 homes with air conditioning, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Winona vacation rentals

Top-rated vacation rentals in Winona

Vacation rentals for every style

Houses

Cabins

Apartments

Popular amenities for Winona vacation rentals

Stay near Winona's top sights

Other great vacation rentals in Winona

Cabin in Mindoro

Cottage in La Crosse

Cottage in Pepin

Apartment in Trempealeau

Loft in La Crosse

Home in Fountain City

Cottage in La Crosse

Cottage in Stoddard

Other great vacation rentals in Winona

Apartment in Winona

Cottage in Winona

Apartment in Winona

Home in Winona

Home in Lewiston

Guest suite in Fountain City

Farm stay in Wykoff

Vacation home in La Crosse

Quick stats about vacation rentals in Winona

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Winona?

Are there pet-friendly vacation rentals in Winona?

Do apartment rentals in Winona have air conditioning?

Do apartment rentals in Winona have wifi?

Are there family-friendly house rentals in Winona?

Do house rentals in Winona have a bbq area?

How much does it cost to stay in house rentals in Winona?

What are the most popular amenities for House Rentals in Winona?

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