Pet-friendly holiday rentals in Winona

Bohemian Bungalow: Live like a Local, Pets Welcome

Nestled in a central, southside neighborhood, conveniently located near shops, restaurants & hospitals. Live like a local with décor from our hometown makers, eat like a local at a crafthouse blocks away or venture a mile to the spacious coffee shop serving espresso, wine & bites or enjoy our fully fenced backyard offering privacy for you & your pets. The detached 2 car garage is available for your use during your visit. We paid special attention to the details to ensure you enjoy your stay.

The Cottage at Heart & Soil Ridge

Welcome to Heart and Soil Ridge! Come experience life on a Minnesota farm nestled in the rolling hills of the Driftless area! Relax outside on the deck, swing in a hammock among the trees, or walk through our beautiful cover crop fields. This is a working farm & depending on the season, you are welcome to help collect eggs, observe the numerous farm animals, learn about regenerative farming, or visit our Fox Red labs. We want your experience at our farm to be relaxing and refreshing!

Beautiful Craftsman Bungalow - Centrally located!

In the heart of La Crosse, this freshly renovated 1920’s Craftsman home is full of character and old-world charm. The home is just minutes from downtown and blocks from both hospitals and all the three colleges. The house features original woodwork, vintage tile, cozy radiant heat, beautiful leaded glass windows, 9 foot ceilings, an upstairs office suite, a large sun porch with French doors, and hardwood floors throughout. Well behaved pets are allowed for an additional fee of $50.00 each

Little House on the Prairie

Enjoy this newly remodeled 2 bedroom 1 bath house located on beautiful lake onalaska only minutes from town, but far enough away to enjoy the quiet peacefulness of nature. There is a large backyard with lake access for year round activities (boating, fishing, kayaking, canoeing, and ice fishing. Schaeffer's boat landing and rentals is just a short walk away, and a popular restaurant is also within walking distance. A beautiful walking/biking trail is nearby, and many other attractions.

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.

Stunning Views! - Pettinger @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. Pettinger cabin is named after Petting Summit located just east of the cabin. Pettinger 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.

Emma’s Cozy Cottage

Our place is a short drive to Lake Onalaska,boat landings and centrally located to popular state parks.The cottage is right next to our Bait and Tackle Shop off of Hwy. 35 and OT.Our area is a popular destination for kayakers,hikers,bikers and fishermen.The Great River Trail is nearby. Many restaurants and bars as well.Our cottage is not remote but very private with many recent updates and secure with no neighbors and a nice yard for your dog.Indoor Hot Tub..Bonus !

Nostalgic Retro Cottage-Faye's Place-Fully Fenced

Welcome to Faye's Place! We are a 2 bedroom/1 bath small Cottage on the Northside of La Crosse with a full fenced in yard! We are right off of 1-90. 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. Ask about our Dive Bar Tour!

Hidden Falls Cabin

Tucked away in one of the Driftless Region's many valleys, you find our quaint cabin over a small bridge that spans our creek. Get a break from the hustle & bustle with us in a cabin with all modern amenities and a handcrafted charm we've worked to cultivate for you. This cabin is on our property where we reside, as well as rental property, with two tenants. All guests and well behaved dogs are welcome for an addition dog fee!