Pet-friendly holiday rentals in Winona

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!

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.

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!

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 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.

~ 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.

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.

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.

Charming Cabin with Hot Tub & Fire Pit

The Paige is an updated 103 yr old cabin. It is family-friendly and dog-friendly; near all the great amenities in Pepin including Villa Belleza (only 0.5 mile away), The Homemade Cafe (one block away), Harbor View Cafe, The Pickle Factory, Lake Pepin, and Stockholm, WI. A great central location for all Lake Pepin area activities!