Pet-friendly holiday rentals in Winona

4.91 out of 5 average rating, 328 reviews

A spacious bedroom features a four-poster bed with soft linens and pillows. Natural light enters through large windows adorned with sheer curtains. Wooden beams highlight the ceiling, while a cozy rug and bedside lamps create a comfortable ambiance.

Cottage in La Crosse

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

PetsWalkabilityAccuracy

4.92 out of 5 average rating, 355 reviews

A spacious living room features a modern fireplace with a black brick surround. Comfortable seating options include a gray sofa and colorful armchairs. A wooden coffee table sits centrally, while a large television is mounted on the wall. Light filters in through sliding glass doors, enhancing the room's inviting ambiance.

Cottage in Stoddard

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! 15 minute drive to downtown La Crosse and 3 miles North of Stoddard puts you in a great central location for the area. Mt. La Crosse is super close to enjoy skiing/snowboarding. Goose Island is 5 minutes away. Great spot for bird watching, fishing, kayaking, boat launches, hiking or frisbee golf. Pets are welcome. No cleaning fee!

Outdoor spacesPetsAmenities

4.93 out of 5 average rating, 133 reviews

The exterior of a remodeled brick church is showcased, featuring large arched windows and a white entry door. Stairs lead up to the entrance, with pumpkins placed on either side, adding a seasonal touch to the landscaped area.

Apartment in Lanesboro

Two story apartment, spacious!

This is a furnished apartment in a renovated church. One bedroom with a queen bed and large walk in closet on the lower level. A stairway takes you to an upper loft with three twin beds. Pack n play available and high chair too, upon request. Pets are welcome. Located a very short walk to Sylvan Park which has a wonderful playground. Plenty of counter space for a gathering. You’re welcome to park your bikes inside the apartment if you don’t mind bringing them up the exterior stairs. :)

WalkabilityPetsComfort

4.98 out of 5 average rating, 159 reviews

The exterior of the farmhouse is showcased, featuring a traditional two-story structure with a large front porch supported by dark columns. Lush green grass surrounds the home, complemented by tall trees in the background, enhancing the serene country environment.

Farm stay in Houston

30 Acre Private Farm W/ Walking Trails - Sleeps 10

Welcome to Smith Family Farm! Our 5th-generation Family Farm was built in 1876 and beautifully renovated. This historic 30-acre retreat offers the perfect blend of peace and play. Located about 5 miles off I-90, we feature a 7-hole disc golf course, private walking trails, and a sun-drenched deck for morning coffee. With space for 10 guests, a Blackstone griddle, and a cozy fire pit, it’s the ultimate Minnesota getaway for families and friends. Come make your own history at the farm!

WalkabilityPetsFamily

4.99 out of 5 average rating, 103 reviews

The exterior of a modern cottage is shown, framed by lush greenery under a partly cloudy sky. A spacious patio area features seating, while large windows reflect the surrounding landscape. A fenced garden area is visible in the background.

Cottage in Lanesboro

Driftless River House *Hot Tub* Modern Cottage

Welcome to the Driftless River House, our renovated modern cottage on the Root River near historic Lanesboro! Enjoy swimming, fishing, bonfires, hot tub, starry skies and stunning sunset views over the Root River. Cook in our modern open kitchen, grill or head into downtown Lanesboro (10 min) for its great restaurants and brewery. With over 60 miles of paved bike trails, world class trout fishing, tubing and kayaking... we know you'll love your stay in the beautiful Driftless region.

PetsWalkabilityGetting around

A well-lit living area features large windows with light filtering through, a patterned armchair, and a gray sofa. A decorative mirror, wall clock, and potted plant complement the space, while the hardwood floor is covered by an area rug with geometric designs.

4.93 out of 5 average rating, 105 reviews

Haven on Huff

Your spacious oasis in central Winona welcomes you for a peaceful and relaxing stay. Haven on Huff is a single family home, adjacent to Winona State University and nearby all the amenities of Winona. Enjoy a large kitchen with dining area, living room with pull-out sofa, and a dedicated office space with desk, TV and chaise that can sleep 1 person. Reserved parking area for multiple cars and a seasonal private patio with grill and seating area tucked away behind the house.

PetsWalkabilityTV

4.98 out of 5 average rating, 204 reviews

A private deck is seen on the upper level, adorned with vibrant flower pots and surrounded by greenery. The view extends towards the Mississippi River and distant bluffs, framed by trees that provide natural shade.

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.

Outdoor spacesWalkabilityHiking

The living room features exposed brick walls and wooden beams overhead. A spacious couch is complemented by two chairs, while a coffee table sits atop an area rug. Natural light fills the space through large windows that offer views of the outdoor patio.

4.98 out of 5 average rating, 265 reviews

~ 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!

WalkabilityPetsCheck-in

4.93 out of 5 average rating, 181 reviews

Nostalgic Retro Cottage-Faye's Place-Fully Fenced

Welcome to Faye's Place! We are a 2 bedroom/1 bath Cottage on the Northside of La Crosse with a full fenced in yard! We are right off of 1-90. 2 Blocks from The Black River! Close to Kwik Trip, Walgreens, Food and Animal Watching! 10 min. away from downtown and UWL! Faye's Place is my childhood home and is a small immersive experience. Themed rooms, nostalgic items, games, toys and a treasure hunt! We decorate for all holidays.

WalkabilityPetsTV

A spacious great room is featured, showcasing a wooden dining table with six chairs. A blue couch adorned with colorful cushions is positioned nearby. The kitchen area, equipped with modern appliances and a bar-style countertop, is highlighted by pendant lighting and plants.

4.93 out of 5 average rating, 109 reviews

Craftsman's Home and Garden in Winona

Relax in a quiet family neighborhood surrounded by a unique garden and large backyard. The great room was designed for cooking and sharing meals with family and friends. Spill onto the front porch to enjoy the views of the bluffs and watch people stroll and bike past. Close to hiking and biking trails of Bluffside Park and St. Mary's University, and just a 15 minute scenic bike ride to the center of town.

PetsOutdoor spacesNearby

A charming house is depicted with dark grey siding and a steeply pitched roof. Large windows provide ample natural light, framed by white trim. A white front door serves as the focal point, flanked by lantern-style lights. Flower pots enhance the welcoming entrance.

4.94 out of 5 average rating, 212 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.

PetsOutdoor spacesQuiet

The kitchen features modern white cabinetry paired with dark countertops. A stainless steel range and hood are installed, with a window above offering natural light. A patterned rug lies on the floor, and potted plants are placed on the windowsill.

4.99 out of 5 average rating, 353 reviews

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.

PetsWalkabilityFamily

Popular amenities for Winona pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A spacious living area is highlighted by a sectional sofa adorned with colorful throw pillows. A circular coffee table sits in the center, surrounded by a patterned area rug. Natural light filters through the large windows with light curtains.

4.95 out of 5 average rating, 211 reviews

Historic Downtown Bungalow

PetsWalkabilityQuiet

A comfortable living area features a light-colored sofa adorned with decorative pillows. A round wooden coffee table sits at its center on a patterned area rug. Natural light filters through dual windows fitted with blinds, and a ceiling fan adds a functional touch.

4.98 out of 5 average rating, 151 reviews

Charming, 1-bedroom, open concept house

WalkabilityOutdoor spacesIndoor spaces

A spacious living room is featured, with a brick fireplace as a central element. Comfortable seating is arranged around a coffee table, and a large window allows natural light to fill the space. A tall lamp and wall decor add inviting details.

4.99 out of 5 average rating, 105 reviews

Spacious Bluffside Home

WalkabilityPetsQuiet

4.8 out of 5 average rating, 116 reviews

The open living and dining area features a wooden dining table surrounded by colorful chairs. A comfortable grey couch and small seating options are arranged for relaxation. Natural light enters through windows, providing a welcoming ambiance. Artwork is displayed on the neutral walls.

Home in Onalaska

Backwater hideaway. Big house with water access.

PetsOutdoor spacesParks

The living area features hardwood flooring and original woodwork. A television is positioned on a wooden console, opposite two cozy seating areas. Light filters through a nearby window, highlighting a dining area visible through an archway. Soft natural elements are present with a rug and decor.

4.86 out of 5 average rating, 219 reviews

Beautiful Craftsman Bungalow - Centrally located!

PetsOutdoor spacesBackyard

4.91 out of 5 average rating, 164 reviews

A spacious backyard is visible, featuring a round firepit surrounded by several green chairs. The house is behind, with a picnic table and an umbrella seen on the patio. Lush grass and trees provide a natural setting, enhancing outdoor comfort.

Home in Stoddard

The River Shack

PetsWalkabilityCheckout

4.98 out of 5 average rating, 199 reviews

Adorable bungalow!

PetsOutdoor spacesTV

The exterior of the A.C. Carter House showcases its Victorian architecture with a prominent gabled roof and a multi-colored facade. Details include ornate window trim and decorative entryway columns, surrounded by lush greenery and flowering bushes, offering a charming yet historic appearance.

4.95 out of 5 average rating, 165 reviews

Historic Carter House-Rivertown Romance-Licensed!

WalkabilityPetsParking

Pet-friendly home rentals with a pool

4.91 out of 5 average rating, 45 reviews

Tiny home in Winona

Tiny Home

Outdoor spacesComfortQuiet

4.84 out of 5 average rating, 50 reviews

A spacious deck surrounds a large above-ground pool, featuring a safety railing and a shaded area from a large sun sail. Lounge chairs are positioned nearby, inviting relaxation in a peaceful outdoor setting.

Home in Onalaska

Secluded home w/pool, hot tub, cold plunge & sauna

PetsKitchenQuiet

5.0 out of 5 average rating, 5 reviews

Cabin in Winona

Cute Camping Cabin - Eagles Nest

Sleep qualityAccuracyAmenities

4.67 out of 5 average rating, 15 reviews

Cabin in Winona

Cute Camping Cabin with Bathroom

PetsCleanlinessSleep quality

4.67 out of 5 average rating, 9 reviews

Cabin in Winona

Cute Camping Cabin - Deer Stop

ValueLocationCheck-in

Private, pet-friendly home rentals

Farm stay in Spring Grove

A wooden porch swing is featured, adorned with blue and yellow decorative pillows. The swing is positioned on a spacious deck, with a yellow door and a window visible in the background, allowing for ample natural light.

Black Hammer Hus | Modern Driftless Farmhouse

Outdoor spacesPetsGetting around

4.98 out of 5 average rating, 128 reviews

4.97 out of 5 average rating, 191 reviews

An aerial view captures the cabin surrounded by expansive greenery and trees. The tranquil waters of the river are visible in the background, with soft hills rising in the distance. The layout showcases nearby structures and open areas, providing a sense of space and tranquility.

Cabin in Stoddard

Rustic River Cabin

WalkabilityOutdoor spacesShared spaces

4.97 out of 5 average rating, 273 reviews

A dining table is set on a covered wooden patio, featuring a variety of breakfast items, including eggs, fruit, and beverages. Lush greenery and tree canopies create a natural backdrop, while the expansive view offers a glimpse of the landscape stretching toward the horizon.

Cabin in Mindoro

Stunning Views! - Bunker Hill @HighPointRetreats

Outdoor spacesPetsCondition

5.0 out of 5 average rating, 63 reviews

The Guest House

Outdoor spacesPetsRiver

4.91 out of 5 average rating, 92 reviews

A dining nook features a round white table surrounded by colorful chairs in green, orange, and black. Natural light filters through two windows, illuminating the wooden floor. A framed art piece and decorative items add character to the welcoming space.

Home in Fountain City

Our Little River House

Outdoor spacesWalkabilityHeating

4.95 out of 5 average rating, 21 reviews

Home in Buffalo City

Mississippian River Cabin

WalkabilityOutdoor spacesAccuracy

4.95 out of 5 average rating, 75 reviews

The renovated barn features a red exterior with a metal roof, framed by green trees. A sunset casts a warm glow over the property, enhancing its rural charm. Nearby structures, including a small outbuilding, add to the idyllic setting.

Barn in Winona

Scrappin' on the Ranch

PetsOutdoor spacesBackyard