Pet-friendly holiday rentals in Winona

Stunning Views! - Bunker Hill @HighPointRetreats

Perched in the solitude of nature, our ridge top cabin offers a picturesque view at one of the top elevations in all La Crosse County. Cozy up to your loved ones, relax with friends, or find inspiration in this luxury cabin in the woods. Bunker Hill sleeps four and is non-smoking. Get your front row sunset seats on the private patio and relax by the fire. Immerse yourself in the tranquility and come stay us. *Check out our six other one-of-a-kind retreats listed on Airbnb located in Mindoro, WI

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

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!

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!

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!

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.

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.

Warbler Lodge

Warbler Lodge is situated within Prairie Island Campground along the backwaters of 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 flora and fauna of the Prairie Island park area.

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.