Vacation rentals in Winona County

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Top-rated vacation rentals in Winona County

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Guest favorite

A vintage Lustron Home is showcased with a light blue exterior and a front yard fenced with metal fencing. Green grass surrounds the home, and a spacious garden can be seen in front, accented by flower beds. Large windows allow natural light to fill the interior.

Home in Minnesota City

4.98 out of 5 average rating, 296 reviews

✨Vintage Lustron Home✨

Enjoy a stay in this vintage Lustron Home. It is a unique home. It has two bedrooms, and a sofa sleeper in the living room. The master bedroom has a queen size bed. The second bedroom has two twin beds. This home offers a washer and dryer for your convenience. It has a large fenced yard to enjoy during your stay. Off street parking and Wi-Fi included. This home is in a very peaceful neighborhood. Located close to Winona State University and St. Mary's University. There are State Parks close also

Top guest favorite

Farm stay in Rushford

5 out of 5 average rating, 16 reviews

Country Chic, Hovde Home at Labrador Farm

Come enjoy the peaceful surroundings of this rustic destination. Surrounded by nature and coupled with many modern luxuries. Breathtaking views from the porches. Cozy up at the fire pit to stargaze or roast some marshmallows. Offload horses, paddock available with water (4-6 with signed waiver). Bring your furry-faced family members ! Do not leave on the property unattended please. Pets are welcome but must be supervised. There is a fee PER pet but all Dogs welcome! Enjoy our hidden gem!

Guest favorite

A well-organized bathroom features light-colored walls and tiled floors. Wooden shelves hold neatly arranged towels and decorative plants. A modern vessel sink sits atop a cabinet, with a mirror above it. Natural light filters in through a window, illuminating the space.

Farm stay in Dakota

4.92 out of 5 average rating, 263 reviews

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!

Guest favorite

A private deck is shown, featuring a small table with two chairs, overlooking a scenic view of the water and trees. Bright blue skies and distant hills are visible in the background. The deck has wooden flooring and a covered roof.

Home in Fountain City

4.96 out of 5 average rating, 128 reviews

River Road Abode: breathtaking river views

Entire 2 bedroom home with amazing views of the Mississippi from every room in the house. 3 unique decks to watch birds, barges, boats, bluffs and trains. Out front you can wave at people passing by on the Great River Road. Located near WI and MN state parks, wineries, breweries, and restaurants. Adventure outdoors or stay in and watch all the Mississippi has to offer from the private patio and decks. Trains pass by property day & night. Home is well insulated & ear plugs are provided.

Guest favorite

A rustic cabin constructed from logs is surrounded by snow-covered ground, featuring a welcoming porch with wooden railings. Red chairs are positioned on the porch, inviting relaxation. The entrance is framed by landscaped bushes, harmonizing with the natural winter scenery.

Cabin in Dakota

4.91 out of 5 average rating, 206 reviews

Secluded cabin in beautiful river valley.

Cozy Cabin in the woods! You can go hiking, cross country skiing, snow showing, bird watching, 5 minutes from the Mississippi River, local shopping in LaCrosse, Wi. and Winona, Mn. Or just simply sitting around the campfire and enjoying the peace and quiet of nature. Great River Bluffs Mn state park is widely known for cross county, and hiking trails! Beautiful views of the Mississippi! Located within minutes. You can enjoy outside dining with our gas grill. Fire wood is available.

Superhost

A circular arrangement of six blue Adirondack chairs surrounds a fire pit set on green grass. Each chair is accented with a red cushion. Trees provide partial shade in the background, with blue tarps covering boats nearby.

Apartment in Winona

4.75 out of 5 average rating, 8 reviews

Port 19

This amazing location is perfect for your getaway! The only home in Winona on the main channel of the Mississippi River! With it's open concept, it features a sunken living room, full kitchen, work space area, W/D, private deck, grill, huge yard, fire pit, and all of this is just waiting for YOU! Trailering your boat? Not a problem! (Must be approved). Boat ramps for launching near by! And walking distance to down town and your favorite watering hole! Come relax and enjoy!

Guest favorite

An attached deck offers a view of Lake Onalaska, featuring a patio table surrounded by four chairs under a large umbrella. A charcoal grill is positioned nearby, and lush greenery lines the edge of the deck, creating a serene outdoor space.

Cottage in Onalaska

4.89 out of 5 average rating, 344 reviews

Northshore Cottage (2 bedrooms) on Lake Onalaska

Come stay at our cozy and comfortable two bedroom cottage located in a quiet neighborhood with views and access to Lake Onalaska. Walk across the street to hiking/biking trails. Near the Great River State Bike Trail. The Lake Onalaska canoe/kayak trail goes past our shoreline. Two sit on top kayaks and two easy ride bicycles are included. There are fishing boat rentals nearby or you can fish from the shore while enjoying Lake Onalaska's famous sunsets. No cleaning fee!

Guest favorite

A spacious window with multiple panes offers views of the Mississippi River and surrounding greenery. Candles are placed along the wooden ledge, providing a serene ambiance. Natural light fills the room, highlighting the tranquil setting beyond.

Home in Winona

4.9 out of 5 average rating, 241 reviews

Winona, MN- Cozy 3 bdrm bungalow with river view

Our home/cabin is up along the bluffs allowing eagle eye views of the Mississippi River. A perfect quiet place to take everything in. There are three bedrooms intended for large families or group get-aways. Everything is at your fingertips from beaches, to hikes in the bluffs. It is 3 miles south of Winona. While you can see the river, there is easy access to public landing if you choose to bring a boat to partake in the various islands and water sports.

Top guest favorite

A second-level view showcases polished hardwood flooring and exposed brick walls. A stylish chandelier hangs from the dark ceiling, illuminating the staircase and landing area. Large windows provide natural light, while a decorative clock and furnishings enhance the inviting hallway.

Home in Winona

4.98 out of 5 average rating, 169 reviews

~ 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!

Guest favorite

A wooden dock extends into Lake Onalaska, surrounded by tall grasses and water vegetation. A simple bench provides a resting spot near the water's edge, with distant hills visible on the horizon under a muted sky.

Apartment in Onalaska

4.88 out of 5 average rating, 227 reviews

Lakefront Studio

Lakefront studio One bedroom studio on the edge of the Upper Mississippi Wildlife Refuge. Surrounded on one side by beautiful Lake Onalaska with prairie walking trails on the other. You will not find a closer view of Lake Onalaska. There are two public boat landings less than a mile away. Stay and experience all that "God's Country" has to offer. Now sleeps three: We’ve added a new folding cot to accommodate an extra guest. *No cleaning fees*

Guest favorite

A serene view of a pond reflects the surrounding greenery and the cabin perched on a hill. Lush vegetation and trees frame the area, with a variety of plants visible along the water's edge, contributing to a tranquil outdoor setting.

Cabin in Onalaska

4.93 out of 5 average rating, 101 reviews

Backwaters lodge

This cabin sits overlooking a beautiful view of the water where you will see all types of wildlife. The eagles sit in the giant oak trees just off the porch. Walk down to the dock and drop a line in for fishing. .The state bike/snowmobile/hiking trail is within 3 minutes. The boat landing is 1 mile away. You have your own private dock. We also just added a hatchet throwing target We charge a 25.00 per visit pet fee.

Guest favorite

A serene view of the lush green lawn extends towards the calm waters of the Mississippi River. A patio area with a table and chairs is visible, alongside an umbrella providing shade. A fire pit and grill are included, enhancing outdoor relaxation options.

Tiny home in Winona

4.96 out of 5 average rating, 134 reviews

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.