Vacation rentals in Winona County

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Top-rated vacation rentals in Winona County

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Guest favorite

A serene lakefront view is captured at dusk, showcasing a gradient of purple and pink hues in the sky. Two trees frame the scene on either side, reflecting gently in the calm water, creating a peaceful atmosphere.

Cottage in Onalaska

4.82 out of 5 average rating, 348 reviews

Lake Onalaska Cabin surrounded by Wildlife Refuge

Two bedroom cabin 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 have access to hiking, biking, kayaking, canoeing, and fishing steps from your door. There are two public boat landings less than a mile away. This cabin has a full kitchen but if you prefer there are several restaurants nearby. Stay and experience all that "God's Country" has to offer. Wi-Fi DVD player *No cleaning fees

Guest favorite

Apartment in Winona

4.94 out of 5 average rating, 253 reviews

2nd Floor Retreat - 7 Blocks from WSU

Our one-bedroom apartment is perfect for two guests. * NO cleaning fee/deposit required * Spacious bedroom with queen size bed, couch and workspace * Fully kitchen with oven, refrigerator, microwave + coffee/tea station * TV, board games and books * All amenities needed for a comfortable stay * Walking distance to WSU and Cotter * Your own washer dryer in the apartment * Easy self-check-in process We want you to love your time in Winona and are here to make your stay as pleasant as possible.

Guest favorite

The living area features a spacious couch paired with a patterned area rug. A flat-screen TV is mounted on a wall, opposite a wooden entertainment unit. A dining table surrounded by four chairs is positioned near the kitchen area, with soft lighting from a nearby lamp.

Farm stay in Dakota

4.92 out of 5 average rating, 275 reviews

The Cottage at The Healing Refuge

Welcome to The Healing Refuge! 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, chat with the horses, observe the numerous farm animals, or learn about regenerative farming. We want your experience at our farm to be relaxing and refreshing!

Guest favorite

A serene view of the Mississippi River is captured, featuring a boat and a paddleboarder on calm waters. Lush green trees line the riverbanks, while gentle hills rise in the background under a cloudy sky.

Home in Fountain City

4.96 out of 5 average rating, 141 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.

Top 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

4.92 out of 5 average rating, 226 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.

Guest favorite

A cozy cabin interior features natural wood paneling throughout. A spacious bed is positioned near a window with views of the surrounding greenery. A leather couch and a rocking chair add to the seating options, complemented by a small table.

Tiny home in Plainview

4.95 out of 5 average rating, 153 reviews

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.

Top guest favorite

A view of the Mississippi River is seen from the apartment, with lush green bluffs in the background. Nearby buildings exhibit charming architecture, and parked cars line the streets. A light post adorned with an American flag stands in the foreground.

Apartment in Trempealeau

4.98 out of 5 average rating, 133 reviews

Small Town Vibes with Amazing River & Bluff Views

Enjoy gorgeous view of the Mississippi River, bluffs, and trains, entertain yourself with the live music (occasionally late) from neighboring establishments, stargaze on the deck, or revel in the passing trains. This apartment is the perfect place to get away and relax. Bring up your boat as you'll have parking available in the driveway too! NOTE: this is an upstairs apartment, but we promise you won't be disappointed and want to come back again and again. NON SMOKING. No pets.

Top guest favorite

A modern kitchen features sleek white cabinetry and stainless steel appliances, including a full stove and dishwasher. An island with seating options is present, with utensils neatly arranged on the wall. Natural light enters through a large window, illuminating the polished wooden floors.

Apartment in Winona

4.98 out of 5 average rating, 155 reviews

~ Third Street Suites ~ #3

This beautiful 2nd story loft suite (accessed by stairs only) is conveniently located in the heart of downtown Winona MN on Third Street! Everything Winona and the downtown area has to offer is within close proximity. Examples include: Coffee, restaurants, bars, brewery, Winona State University, Mississippi River, Lake Winona, hiking trails, Shakespeare Festival, Minnesota Marine Art Museum, and much more! Please allow us to make your next stay in beautiful Winona a memorable one!

Top guest favorite

A private deck is seen on the upper level, adorned with vibrant flower pots and surrounded by greenery. The view extends towards the Mississippi River and distant bluffs, framed by trees that provide natural shade.

Home in Fountain City

4.97 out of 5 average rating, 153 reviews

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.

Superhost

A fire pit with a stone tabletop is positioned on a patio, featuring glowing flames and natural stone. In the background, rolling green fields and grazing cattle are visible under a soft evening sky, creating a rural ambiance.

Tiny home in Dakota

4.84 out of 5 average rating, 105 reviews

Pleasant Pastures, Dakota MN

Get cozy and settle into this rustic space. Spend some time at our farm in SE MN enjoy watching the cattle graze, beautiful Ridge top sunrises & sunsets and enjoy an outdoor meal with one of our delectable steaks! This is a true working farm, our family operates 600 acres of crop land along with 200 head beef cattle, go ahead and check out the cattle and pigs, or take a hike through our 3 miles of trails through our woodland!!

Top guest favorite

The expansive home is nestled among a vibrant forest of fall foliage, showcasing a rich palette of oranges, yellows, and greens. Large windows reflect the natural beauty surrounding the property, offering a serene view of the landscape.

Home in Winona

4.97 out of 5 average rating, 173 reviews

Beautiful Views of the Mississippi river

This spacious 6300 sf home sits on 18 wooded acres and overlooks the Mississippi and is ideal for large groups. We can accommodate up to 14 guests. 5 bedrooms with 10 total beds. 2 kings, 3 queens, 5 twins. There’s also a pull out couch and additional mattresses. Large, fully stocked kitchen. 2 refrigerators and 3 large living rooms. Coffee maker and coffee. We have one outdoor security camera. Sorry, No pets.

Guest favorite

The exterior of a contemporary tiny house is shown, featuring a mix of wood and metal siding. A small patio area includes a black seating arrangement and a storage box. A covered grill area is visible nearby, surrounded by grassy landscaping.

Tiny home in Winona

4.93 out of 5 average rating, 100 reviews

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.