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

A Suite Getaway
You'll love this place because of the spectacular views, horses, wildlife, fishing, hiking and hot tub for relaxing, a romantic getaway or simply just girl time. This spot is perfect for couples or solo adventurers! A unique suite is attached to an elegant vintage peg barn. Space for bringing horses, snowmobiles or ATV's since we have trails. A mile away from snowmobile trails and 25 mins from a State Park. Also, perfect for snowshoeing and cross country skiing. Fire pit available as well.

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

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.

Grapevine Log Cabins 2
Grapevine Log Cabins, based in Sparta WI, offers pet friendly cabin rentals on a family dairy farm. Amenities and activities include: a walking trail, bike trail, cows in pasture, indoor and outdoor fireplaces, grills outside (there is no cooking in the cabins), Air Conditioning, Heat and firewood is supplied. Nearby activities include: canoeing, fishing, 4 wheeling, antiquing, and superb scenic sites. Pet Policy: Pets may stay with you for an extra $25 per pet/night.

~ 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!

Woods Edge Cozy Retreat @Whispering Winds
Immerse yourself in nature & experience the magic of the lush gardens, free-roaming bunnies, fairy walkway, stargazing area w/ telescope, meditating in the Soul Garden, fishing in the fully stocked trout stream and more. 5 minute walk to City Park w/ frisbee golf, less than 0.5 miles to local restaurants & shops. Come relax, rejuvenate, and live out your best life at Whispering Winds Micro Retreat! (420 & pet friendly)

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).

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.
Popular amenities for Winona pet-friendly home rentals
Pet-friendly house rentals

The Driftless House - Winona, MN

Adorable bungalow!

Historic Carter House-Rivertown Romance-Licensed!

Beautiful house in NW Rochester

Charming Historic Home est. 1898

Secluded Modern Farmhouse

Historic Downtown Bungalow

Castle Vue Villa & Outdoor Oasis (River Views)
Pet-friendly home rentals with a pool

2 Bedroom Condo - Sleeps 6 (upper level)

2 bdrm Furnished Apt Across from Saint Marys Hosp

3 Bedroom home (sleeps 8)

Studio Apartment

3 Bedroom Condo - Sleeps 6 (upper level)

Secluded home w/pool, hot tub, cold plunge & sauna
Private, pet-friendly home rentals

Our Little River House

Bell Tent Rustic Hike-in Blufftop Glamping -Betula

Riverview Radiance: 5BR, Scenic Views, Pets OK

Outsider's Rustic Retreat

Birch Studio -Cozy studio near quaint river towns!

The Guest Nest

Howling Creek Cabin, Hatfield, Black River Falls

Charming Rosemorr Cottage
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 $98 CAD 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 and kid-friendly amenities
Wifi availability
10 of Winona vacation rentals include wifi 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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