Vacation rentals in Winona County

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Top-rated vacation rentals in Winona County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Minnesota City

4.98 out of 5 average rating, 296 reviews

✨Vintage Lustron Home✨

Li-EnRating, 5 stars1 week ago
We stayed here a second time as it was a great overall experience. Wendy communicated well and was accomodating to our request. It was clean and well furnished. They have a new lazy chair and installed new carpeting.
Guest favorite

Farm stay in Dakota

4.92 out of 5 average rating, 260 reviews

The Cottage at Heart & Soil Ridge

WilliamRating, 5 stars1 month ago
We really enjoyed our short stay. Lance was wonderful and willing to answer questions and show us around the farm. My daughter lived him showing and telling her about the horses. The space was nice. We were meeting with my wives friends for the day and gathered at the farm rekindling of friendships. It was cozy and met our needs. There was plenty of space for the 3 adults, 1 child, and 2 dogs that were staying in the cottage. My daughter really enjoyed the loft and the relative privacy. We would definitely stay again if we are in the area again.
Guest favorite

Home in Fountain City

4.96 out of 5 average rating, 127 reviews

River Road Abode: breathtaking river views

AndreaRating, 5 stars1 month ago
We had a great and cozy time. Loved all the thoughtful and creative touches. The trains were close and loud, which was quite amazing. One of us slept poorly due to the trains, the rest of us loved them. The river views are great.
Guest favorite

Cabin in Dakota

4.91 out of 5 average rating, 199 reviews

Secluded cabin in beautiful river valley.

DeborahRating, 5 stars1 month ago
The cabin is a delightful space and location is scenic. The stove with a fireplace feel in the main area adds a lot to the experience. The hosts were responsive and assisted me after I accidentally locked myself outside of the cabin. Thanks for offering me and my guest and wonderful wintery weekend . Debbie also was flexible and allowed me to shift my dates by one day due to scheduling conflicts
Guest favorite

Cottage in Onalaska

4.88 out of 5 average rating, 335 reviews

Northshore Cottage (2 bedrooms) on Lake Onalaska

JesseRating, 5 stars2 weeks ago
Host was great and very communicative. The place was very nice and well priced. Overall great experience.
Guest favorite

Home in Lewiston

4.99 out of 5 average rating, 104 reviews

Rolling Ridge Retreat

ChristopherRating, 5 stars1 month ago
Paul and Katie were wonderful hosts and their Airbnb was perfect in every way. Everything is brand new, immaculate, and they truly care about their guests. I would highly recommend staying there for a quiet and peaceful retreat. Perfect location, close to Winona, and enjoy the beauty of Minnesota.
Guest favorite

Home in Winona

4.9 out of 5 average rating, 234 reviews

Winona, MN- Cozy 3 bdrm bungalow with river view

CeciliaRating, 5 stars1 month ago
This is the second time we have stayed here, both times at Christmas. The house was beautifully decorated for Christmas including a tree and outside lights. This is probably the best stocked kitchen I have ever had at a rental. There were lots of dishes, glassware, and pots and pans to make meals. There were also staples like flour, sugar, Zip-Lock bags, coffee and a vast array of spices!!! There were toys in the basement that my 7 yo granddaughter enjoyed. The beds were comfortable and many throw blankets to snuggle under if you wanted. I had a few questions for Holly and she was super fast at responding to me. We love this place and hopefully will spend more time here!
Guest favorite

Home in Winona

4.98 out of 5 average rating, 155 reviews

~ 71 Johnson Street ~

RhondaRating, 5 stars2 weeks ago
Love this Airbnb!
Guest favorite

Apartment in Onalaska

4.88 out of 5 average rating, 220 reviews

Lakefront Studio

KristinRating, 5 stars4 months ago
Beautiful! My son and I stayed for a soccer tournament in La Crosse and I’m heart broken that we couldn’t spend more of our time at the cabin. The views are breathtaking and so calming. My son that is typically on his phone was watching ducks and enjoying the waves on the lake/river. The cabin itself is cozy and “basic” - perfect! The bed was like sleeping in a cloud!! I cannot wait to come back (without kids) and actually enjoy the space. ❤️
Guest favorite

Cabin in Onalaska

4.93 out of 5 average rating, 100 reviews

Backwaters lodge

KeithRating, 5 stars2 weeks ago
Our stay at Backwaters lodge was a good time, the cabin is really nice and the scenery is beautiful. Dan is absolutely amazing, I have never had a host care about his guest like he does! If going to La Crosse area I highly recommend staying here. Thanks again Dan! I'll definitely be back!!!
Guest favorite

Tiny home in Winona

4.96 out of 5 average rating, 134 reviews

Potluck String Lodge (PSL)

SallyRating, 5 stars4 months ago
Arriving late to the campground, Anne made it very easy for us to slide in after hours . Very accommodating .
Superhost

Home in Onalaska

4.81 out of 5 average rating, 101 reviews

Relaxation on the river!

SamuelRating, 5 stars1 month ago
The stay was just what we needed to gather family for Christmas. Very spacious, and great accommodations for families traveling with kids. Plan to utilize this space again in the future! Communication during the stay was great, but we did have to call the host the day of to get the code for check-in as we didn’t receive a message response. Not necessarily an issue but something to be aware - two of the bedrooms upstairs and the bathroom have skylights.

Popular amenities for Winona County vacation rentals

Other great vacation rentals in Winona County

Guest favorite

Home in Trempealeau

4.85 out of 5 average rating, 20 reviews

Charming home with views of the Mississippi River

MatthewRating, 5 stars3 months ago
Jon was a great and flexible host. Great views of the river, the lock and damn, and MN bluffs. We were holding an early Thanksgiving and the place met our needs well. Some guests thought there should have been a TV in living room (there is a HUGE one downstairs) but others felt it was good to eliminate that a as a potential distraction.
Guest favorite

Guest suite in Fountain City

4.94 out of 5 average rating, 65 reviews

Backwaters Bungalow: waterfront/next to state park

BreannaRating, 5 stars1 month ago
We really enjoyed our stay - what a beautiful place. We felt right at home… thank you so much Lisa, would love to return in the summer!
Guest favorite

Home in Winona

5 out of 5 average rating, 12 reviews

Waterfront | HOT TUB | Sleeps 15

AprilRating, 5 stars6 days ago
This home was just as pictured. It was so cozy and there was so many options for activities to do while there!
Guest favorite

Home in La Crescent

5 out of 5 average rating, 19 reviews

The Castle on the Hill

OlenaRating, 5 stars1 month ago
We stayed in the “Castle on the Hill” for a girlfriends’ retreat and truly enjoyed the property, all the amenities and the hospitality of the hosts. The house is spacious, conveniently located close to the main freeways and local attractions. Everything you could think of for a relaxing stay was provided and the hosts were responsive and gracious!
Guest favorite

Barn in Dakota

4.87 out of 5 average rating, 95 reviews

Renovated Barn Sure To Impress w/ Loft & Game Room

SabrinaRating, 5 stars1 week ago
This was our second time staying at Jaimie’s place and we absolutely loved it! Always clean and close to all the fun downtown LaCrosse has to offer!
Guest favorite

Home in Winona

4.97 out of 5 average rating, 147 reviews

Beautiful Views of the Mississippi river

LoganRating, 5 stars3 weeks ago
What a great find! The home is close to Winona, but very private and secluded, with incredible views. Tons of space, everything was spotless, and check in was a piece of cake. Scott was very proactive with his communication, which made our arrival and departure very simple.
Superhost

Apartment in Winona

4.65 out of 5 average rating, 17 reviews

The Exchange 13 | Historic Bldg, Studio, Dwntwn

ThomasRating, 5 stars6 months ago
We love the Exchange so much, we came back for another visit. It is a really cool historic building and this studio had plenty of room and felt very spacious. The unit is well furnished, has been recently remodeled, clean and feels very safe. #13 is conveniently located on the main level right by the back entrance to the parking lot. The building’s location is awesome! So many bars, restaurants, shops, breweries, movie theater, grocery store, and the Mississippi River walk at Levy Park all with in walking distance (1-4 blocks). Some of our favorites were Bubs Bar and grill next door (great food, affordable drinks), Blooming Ground coffee house (2 blocks), Peter’s Biergarten (outdoor drinks with live music, BYO food, 2 blocks away), Nate & Ally’s Ice-cream Shop (3 blocks away), and Muddled Thyme for some higher class cocktails/wine alone with some great firebrick oven pizza ( 2 blocks away). We highly recommend the Exchange and can’t wait to come back to visit.
Guest favorite

Home in Trempealeau

4.88 out of 5 average rating, 41 reviews

The BRD Nest Mississippi River Home with Views

GinnyRating, 5 stars1 month ago
For the second time my 3 generation family was able to celebrate our annual winter holiday together at the lovely Bird's Nest. We do a traditional Smorgasbord that requires a well equipped kitchen and this certainly meets that need. The house is very clean and nicely decorated. The view is breathtaking, and the hosts are extremely helpful. The Erling's love it there!

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