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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

Private Farm House 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!

Our Little River House

A cozy, 2 bedroom, 2 bathroom home nestled in the bluffs of Fountain City, WI two blocks off the Great River Road. The house sleeps six comfortably w/ four brand-new extra-long twin beds that can be combined to form two king-sized beds. There is also a queen-sized bed with a single bunk bed above it in the master bedroom This house has a fully stocked kitchen, fenced-in backyard w/ fire pit, off-street parking for 1 vehicle and view of the Mississippi River from the kitchen window!

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 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!

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.

Dragonfly Loft, hot tub, river views

Welcome to our cozy retreat in Fountain City, Wisconsin, where the serene beauty of nature meets the charm of small-town living. The Mississippi River is your backyard! Our inviting 2-bedroom, 1.5-bathroom vacation rental comfortably accommodates up to 4 guests and warmly welcomes furry friends, making it the perfect getaway for families and outdoor enthusiasts alike. Train track, firepit, hot tub, oh my! Ask us about our weekly specials!

Craftsman's Home and Garden in Winona

Relax in a quiet family neighborhood surrounded by a unique garden and large backyard. The great room was designed for cooking and sharing meals with family and friends. Spill onto the front porch to enjoy the views of the bluffs and watch people stroll and bike past. Close to hiking and biking trails of Bluffside Park and St. Mary's University, and just a 15 minute scenic bike ride to the center of town.

Cozy 1 bed 1 bath cabin #12

UNDER NEW MANAGEMENT! 1 bed 1 bath fully furnished private unit in the quiet, safe, and quaint town of Dresbach with scenic views of the Mississippi River just across the street. All units are professionally cleaned. Off street parking available. Coin operated laundry available on the premises. Max of 2 house broken, well behaved pets with current vaccinations are welcome for a fee.

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.

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.