
Pet-friendly vacation rentals in Winona
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Winona
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

Enjoy 36 Acres in a private Farm House - Sleeps 10
Welcome to Smith Family Farm! Our fifth-generation owners converted the historic family farmhouse into a charming and functional Minnesota vacation house rental. With sleeping arrangements for 10 guests, modern amenities, and 36 acres of private land, our property offers everything you need for a peaceful getaway. Originally built in 1876, the 2,250-square-foot house has two stories, three bedrooms, and two bathrooms, and an additional murphy bed in the sunroom. Full Kitchen, Dining, Living.

The Bungalow at the Healing Refuge
Welcome to The Healing Refuge! 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, learn from the horses, observe the farm animals, and find out about regenerative agriculture. We want your experience at our farm to be relaxing and refreshing!

Stylish 1 bedroom cottage on the Mississippi River
This unique place has a style all its own. Conveniently located by the Mississippi River and highway 35. The place gives you a cabin feel close to La Crosse! Goose Island is 5 minutes away. Great spot for bird watching, fishing, kayaking, boat launches, hiking or frisbee golf. Mt. La Crosse is super close to enjoy skiing/snowboarding. 15 minute drive to downtown La Crosse and 3 miles North of Stoddard puts you in a great central location for the area. Pets are welcome. No cleaning fee!

Cheerful Cottage Near the Bay
Relax into the slower pace of river life. We are located on a laid back street where everyone is ready with a friendly wave or a driveway chat. The boat landing is just a mile away. The house is stylish and comfortable. We hope to provide our guest with whatever the need for a few days away. We are in a high PFAs area so bottled water is provided for guest consumption. More information available at: townofcampbellwi website under well-water-pfas-information License number MWAS-D42N9M

Back 20: Hike in only secluded tiny cabin
A beautiful, private, hike in only spot. Quiet Dry Cabin in perfect seclusion to get away from it all. No TV, no phone, no AC, or Internet. When you book this home you are truly wanting to unplug... 1 bedroom loft cabin nestled into 20 acres of trees, valleys, and corn fields. This is roughing it! Natural deep woods within a gully between fields, you’ll find this spot a wonderful sanctuary for wildlife. Follow the few scattered deer trails on the property and explore this natural place.

Quaint 1 bedroom cabin, with amazing views!
Peaceful 1 bedroom cabin overlooking views of the beautiful whitewater valley (35 minutes away from Rochester Minnesota). Perfect for a quiet, off-the-grid, retreat. - compost toilet -two burner stove -gas heater for the colder months -5 gallons of water included, more If needed Queen size bed beneath 3ft by 3ft skylight with stunning views of stars at night. 120 private acres connected on two sides by the (WMA). 1 + mile of personal private hiking trails with scenic views.

Bluffside cottage with gorgeous 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.

~ 71 Johnson Street ~
This beautiful brownstone house is conveniently located in the heart of beautiful downtown Winona MN! It is within close proximity to many attractions Winona has to offer such as: Mississippi River front access, coffee shops, restaurants, bars & lounges, Winona State University, Lake Winona, hiking/biking trails, Shakespeare Festival, Minnesota Marine Art Museum, and much more! Please allow us to make your next stay in beautiful Winona a memorable one!

Backwaters lodge
This cabin sits overlooking a beautiful view of the water where you will see all types of wildlife. The eagles sit in the giant oak trees just off the porch. Walk down to the dock and drop a line in for fishing. .The state bike/snowmobile/hiking trail is within 3 minutes. The boat landing is 1 mile away. You have your own private dock. We also just added a hatchet throwing target We charge a 25.00 per visit pet fee.

Trout Creek Cabin
The cabin sits in a valley on the South Fork of the Root River. Fire pit, hot tub and 2 large patios both with outdoor dining, steps away from the trout stream make this unique property a peaceful, romantic get away. A short drive from the Root River bike trail and Lanesboro making it easy to take advantage of the best historic bluff country has to offer.

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.

Burton House (Downtown Winona)
The Burton House is a recently renovated, cozy little home just a few blocks from downtown Winona, MN and the mighty Mississippi River. It is walking distance to several restaurants, bars and shops. It's the perfect launch pad for outdoor enthusiasts, with wonderful recreation opportunities in and around Winona.
Popular amenities for Winona pet-friendly home rentals
Pet-friendly home rentals with a hot tub

A Suite Getaway

Riverview Radiance: 5BR, Scenic Views, Pets OK

Peace of Pepin- 2nd story hot tub!

Waterfront | HOT TUB | Sleeps 15

New Hot Tub Nov 2025, Firepit, Eco-Friendly

Comfy, Large, Pet-friendly! Near Mississippi River

Driftless River House - *Hot Tub* Modern Cottage

Secluded home w/pool, hot tub, cold plunge & sauna
Pet-friendly house rentals

Sweet Home, 2 Miles to Winona Health!

Farm House Beauty

The River Shack

The Driftless House - Winona, MN

Lovely bungalow!

Historic Carter House-Rivertown Romance-Licensed!

Nostalgic Retro Cottage-Faye's Place-Fully Fenced

Historic Downtown Bungalow
Private, pet-friendly home rentals

b3 Couples Therapy Yacht

Convenient, Family friendly!

HOUSE ON THE RIVER

The Alton House - Experience tiny house living

Betty's House A relaxing home in the country...

House on the Water

NEW Build with Indoor Oasis | Party/Game Room

Prairie View Farm
When is the best time to visit Winona?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$29,938 GYD | G$29,938 GYD | G$30,566 GYD | G$32,869 GYD | G$34,753 GYD | G$34,753 GYD | G$38,312 GYD | G$38,103 GYD | G$35,800 GYD | G$35,172 GYD | G$33,916 GYD | G$33,079 GYD |
| Avg. temp | -7°C | -5°C | 2°C | 10°C | 16°C | 22°C | 24°C | 23°C | 18°C | 11°C | 3°C | -4°C |
Quick stats about vacation rentals that are pet-friendly in Winona

Total vacation rentals
Explore 10 vacation rentals in Winona

Nightly prices starting at
Winona vacation rentals start at G$14,655 GYD per night before taxes and fees

Verified guest reviews
Over 1,860 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Wi-Fi availability
10 of Winona vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winona rentals

4.9 Average rating
Winona stays are highly rated by guests—averaging 4.9 out of 5!
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