Pet-friendly holiday rentals in Winona County

Parkside Pet Friendly Bungalow

Cozy 3-Bedroom Bungalow Near Lake Winona – Pet-Friendly! Located in a quiet neighborhood. Relax in this charming, family-friendly home just steps from the Lake Winona walking path, dog park, and WSU. Features a fenced yard, firepit, gas & flat-top grills, plus Smart TVs in every bedroom. Queen bed in 2 bedrooms and a full-over-twin bunk in the other. Great for couples, families, or remote workers. Please park in the back (off the alley) or on the street—do not use the driveway next to the home

The Guest House

Modern one-bedroom home— bright, fresh, and fully updated! This beautifully designed one-bedroom space seamlessly blends modern comfort with calming touches, making it perfect for relaxing after a long day of work, travel, or adventure. The home is just minutes from Winona’s lakes, trails, dining, and downtown attractions. Whether you’re here for outdoor adventure, a weekend getaway, or a comfortable remote-work base, this space offers everything you need for a smooth and enjoyable stay.

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.

The Guest Nest

Escape to the Guest Nest! Immersed in nature, the beautiful landscape of the Driftless region valleys are one of the world’s most beautiful locations to explore. Walk the roughly 2 acre yard of grass and wildflowers. Enjoy a cup of coffee by the creek. Play a yard game. Or just sit on the deck and enjoy all the sights and sounds and solitude. Watch for deer, turkey, an occasional black bear, and an abundance of song birds, humming birds, and other small critters.

~ 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!

Nana & Papa's

Welcome to Nana & Papa's, our home away from home. Tucked in the corner of Minnesota, nestled between bluffs & water, Winona is the perfect getaway. Within minutes of lakes & the Mississippi, our home is in a quiet neighborhood, within walking distance of parks & a cozy cafe. You will have our entire property to yourselves, & we are only a phone call away should you need anything. We look forward to your stay, & hope you love this home as much as we do.

The Driftless House - Winona, MN

Located In the Driftless region of the Mississippi River Valley, this home offers 3 large bedrooms (1 King bed/2 queen beds), a full yard, on-site laundry, full kitchen, and a relaxing front porch. This home is conveniently located in a residential neighborhood close to downtown, Lake Winona, restaurants, and more. This home also comes with most things needed to care for small children, including: toys/games, Pack 'n Play, highchair, and stroller.

Potluck String Lodge (PSL)

Potluck String Lodge (PSL) is situated within Prairie Island Campground along 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 Boats and Bluegrass music festival and one of the campground picking circles hosted by the Potluck String Band.

Scrappin' on the Ranch

Scrappin’ on the Ranch is designed specifically for anyone who needs a place to stay. We are located 20 minutes from La Crosse, Wis., and 15 minutes from Winona, Minn. Scrappin’ on the Ranch is a renovated barn trees tucked in the bluffs of the Mississippi River Valley. The property is located on 80 acres of natural beauty. The perfect setting from inside and out for those who want to get away.

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.

River Shack Retreat

Bonfires under the stars. One of Wisconsin’s prettiest state parks. The best local winery. Miles of bike trails. Apple orchards galore. Just minutes from it all, this newly remodeled cottage makes it easy to do as much—or as little—as you want during your stay in picturesque Trempealeau.