Pet-friendly holiday rentals in Winona

4.91 out of 5 average rating, 333 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

4.97 out of 5 average rating, 280 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

Picture perfectly placed atop one of La Crosse counties highest ridges, Bunker Hill offers breathtaking views, in unmatched tranquility. Unwind to the sounds of nature, spectacular sunsets, and find inspiration in pure serenity. Whether you're looking to spend time relaxing with family and friends, enjoy an intimate evening, or simply finding peace in nature, an unforgettable Wisconsin escape awaits at High Point Retreats. We look forward to making your stay as memorable as our views.

4.92 out of 5 average rating, 362 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!

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, 215 reviews

Historic Downtown Bungalow

Central location and private back yard make this a perfect base camp in La Crosse! You’ll appreciate the historic character of the home along with modern updates for a comfortable stay whether you’re visiting town alone or enjoying with family or friends. We’re walking distance to downtown, universities, and hospitals. You’ll have a private driveway for parking up to 4 cars and our fenced back yard is nicely tucked away with patio, deck, and gas grill to enjoy your time at home base.

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!

4.99 out of 5 average rating, 105 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.

4.94 out of 5 average rating, 108 reviews

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.

Home in Winona

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.

4.98 out of 5 average rating, 206 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.

4.98 out of 5 average rating, 269 reviews

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.

Home in Winona

~ 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!

4.96 out of 5 average rating, 304 reviews

A wooden sauna is positioned in the center of a rustic room with exposed beams and corrugated metal walls. Two wooden rocking chairs sit nearby. Light enters through several windows, and a basket is placed on the floor, enhancing the inviting, serene environment.

Home in Stockholm

Bogus Valley Holm Country/Farm Pepin/Stockholm

Come to the country and enjoy lodging at our Bogus Valley Holm. Located in picturesque Bogus Valley, between Pepin and Stockholm Wisconsin. Just a short drive to the area wedding venues and other West Coast Wisconsin attractions. This vintage home farmstead on 4 acres, was built in the mid 1850s and has old world character architecture with the comforts of modern-day amenities. If you are looking for a quiet rural getaway, this is your place.

A living area features a two-tone sofa complemented by a wooden coffee table, which holds neatly stacked books. Warm wood flooring enhances the space, illuminated by modern floor lamps. Natural light filters through two windows with light-filtering shades, contributing to a cozy ambiance.

4.95 out of 5 average rating, 133 reviews

Modern, Renovated Home in the heart of LAX

Retreat or relax after an exciting day-trip hiking or biking the Bluffs, while enjoying tiny living, centrally located in the heart of La Crosse. This property has two bedrooms, a large kitchen/living area, and a bathroom with laundry. It is positioned near two major healthcare systems and University. A short commute via car or bike opens opportunities to explore the downtown area and river with all its recreational experiences.

5.0 out of 5 average rating, 153 reviews

A modern cabin is situated on a grassy plot, surrounded by trees displaying autumn colors. The structure features a dark roof and a wooden door, with patio seating visible on the deck. The landscape includes gentle hills and a clear sky.

Cabin in Lanesboro

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.

Popular amenities for Winona pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.93 out of 5 average rating, 184 reviews

Nostalgic Retro Cottage-Faye's Place-Fully Fenced

4.98 out of 5 average rating, 203 reviews

Lovely bungalow!

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, 109 reviews

Spacious Bluffside Home

4.98 out of 5 average rating, 130 reviews

A serene landscape showcases rolling green pastures bordered by lush trees. The expansive sky is filled with soft, wispy clouds, creating a calm atmosphere. Fenced areas are visible in the foreground, highlighting the rural setting and natural beauty of the surroundings.

Home in Plainview

EXPERIENCE COZY home! Goats, sheep, cattle, views!

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, 220 reviews

Beautiful Craftsman Bungalow - Centrally located!

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

4.86 out of 5 average rating, 102 reviews

Home in Pepin

Lake Port - relax & unwind

4.99 out of 5 average rating, 117 reviews

King Beds | Fenced Yard | Near Downtown

Pet-friendly home rentals with a pool

4.9 out of 5 average rating, 51 reviews

Tiny home in Winona

Tiny Home

4.85 out of 5 average rating, 52 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

5.0 out of 5 average rating, 5 reviews

Cabin in Winona

Cute Camping Cabin - Eagles Nest

4.69 out of 5 average rating, 16 reviews

Cabin in Winona

Cute Camping Cabin with Bathroom

4.73 out of 5 average rating, 11 reviews

Cabin in Winona

Cute Camping Cabin - Deer Stop

Private, pet-friendly home rentals

4.91 out of 5 average rating, 254 reviews

An open kitchen area features wooden cabinetry and stainless steel appliances, including a refrigerator and oven. A dining table with six chairs is placed centrally, with a ceiling fan providing airflow. Natural light enters through large windows, illuminating the light hardwood flooring.

Apartment in Cochrane

Rut'n Duck Lodge

4.93 out of 5 average rating, 139 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.

Flat in Lanesboro

Two story apartment, spacious!

4.96 out of 5 average rating, 196 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

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

4.98 out of 5 average rating, 131 reviews

4.98 out of 5 average rating, 96 reviews

A charming yellow house with a front porch is set in a residential neighborhood. The well-maintained lawn is bordered by a wide sidewalk, leading to the entrance. Large windows allow for natural light and offer views of the surrounding greenery, enhancing the inviting exterior.

Home in Winona

The Driftless House - Winona, MN

4.95 out of 5 average rating, 21 reviews

Home in Buffalo City

Mississippian River Cabin

4.92 out of 5 average rating, 95 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