Vacation rentals in Winona

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Popular amenities for Winona vacation rentals

Stay near Winona's top sights

Minnesota Marine Art Museum32 locals recommend
Garvin Heights Lookout17 locals recommend
Island City Brewing Company Co14 locals recommend
Blue Heron Coffeehouse15 locals recommend
Acoustic Cafe15 locals recommend
The Boat House Restaurant14 locals recommend

Vacation rentals with pools in Winona

Guest favorite
A modern, single-story house is set among lush greenery, featuring a welcoming front porch with steps leading to the entrance. A driveway accommodates vehicles, while the yard is adorned with well-maintained grass and a variety of plants. Nearby structures are visible, contributing to the neighborhood's charm.
Home in La Crosse
4.96 out of 5 average rating, 28 reviews

Brand New, 3 Bed/ 2 Bath w/ Parking on UWL Campus

JennyRating, 5 stars6 months ago
Cute house in a great location on campus!
Guest favorite
Tiny home in La Crosse
4.9 out of 5 average rating, 162 reviews

Come unwind with us at Kindred Tiny House.

DrewRating, 5 stars4 days ago
Had a great stay here, lots of fun to stay in downtown Lacrosse and a great place to come back to at the end of the day and relax!
Top guest favorite
Two individuals are seated in a green float in the expansive pool, overlooking a vast landscape. The sun shines brightly above, casting reflections on the shimmering water, while rolling hills and trees extend into the distance.
Home in Rochester
5 out of 5 average rating, 38 reviews

RARE! Pool, hot tub, garden &chickens! 4m to Mayo

LezliRating, 5 stars3 months ago
Tiffany’s place was a great location for our annual girls weekend trip. We loved taking advantage of the hiking trails, hot tub and fireplace! The space was perfect for 7 adults, and we enjoyed our time. This is not a complaint but just a heads up for future guests - there is only a Keurig, no coffee maker. We’re big coffee drinkers, so we had to pivot a bit but it was no big deal. 😊 Thanks Tiffany!
Guest favorite
A farmhouse-style kitchen is seen, featuring a large stainless steel sink and a dishwasher. Bright yellow lemon decor hangs on the walls, and a bouquet of colorful flowers rests on a wooden island. The cabinetry is white, complementing the green walls.
Farm stay in Dakota
4.89 out of 5 average rating, 228 reviews

The Lodge at Heart & Soil Ridge

JohnathanRating, 5 stars2 weeks ago
Our stay was wonderful! The family is very friendly and helpful with whatever we needed. We enjoy a farm atmosphere. They have a beautiful farm and friendly animals. We got to meet their animals and especially enjoyed spending time with the horses. The pool and hot tub were amazing! My 4 boys, my nephew, my mom, my husband, and I all had a great time playing in the pool. It felt wonderful to relax in the hot tub as well. The house was very nicely decorated, and the furniture was comfortable. They have a lot of what you need in the kitchen and bathrooms, so you don't have to bring as much extra stuff. It was a good size house for our group. We could do some fun things together yet also have enough space to do our own thing when we wanted to. They have fun things to do inside and outside, which is helpful when you don't know what the MN weather is going to do. They have some games in the living room and a big dining table to play games on. Thanks again for an amazing trip!
Guest favorite
An expansive above-ground pool is surrounded by a wooden deck, featuring lounge chairs and poolside seating. Lush greenery and trees are visible in the background, creating a serene outdoor environment. A basketball hoop and wooden surfaces enhance the recreational space.
Home in Onalaska
4.84 out of 5 average rating, 19 reviews

Cozy, quiet place w/pool/hot tub

MonicaRating, 5 stars2 months ago
Mindy was great from the start of the Airbnb and to the end! She was very responsive when we asked for local pizza recommendations in town and confirmed our questions without hesitation even when she was trying to enjoy her own Vacation! She was so nice and her home is amazing! Enjoyed the hot tub and how spacious her whole hole layout was. Would love to stay again here with my girlfriends.
An inviting outdoor swimming pool is framed by a spacious wooden deck. Several blue umbrellas provide shade for the nearby seating area. Lush greenery and hills form a natural backdrop, enhancing the serene atmosphere of the secluded log home.
Home in Alma
4.77 out of 5 average rating, 13 reviews

The Shack

JessicaRating, 5 stars8 months ago
The Shack was exactly what we needed for a quick family getaway. We appreciated the tranquility and scenery of the countryside with the convenience of being just minutes away from restaurants and a picturesque distillery. Our daughters loved the treehouse, slide, and pool. They want to visit again but stay longer next time. :-) Tim was great to work with, attentive and helpful.
Top guest favorite
A blue above-ground pool is surrounded by a wooden deck, with a ladder providing access. The back of the house is visible, featuring large windows and a spacious deck area. Lush greenery and a nearby umbrella enhance the outdoor setting.
Home in La Crosse
4.99 out of 5 average rating, 75 reviews

3BR 3BA w/ Hot Tub, near LaX' Top Rated Activities

WendyRating, 5 stars2 months ago
This was a great place to stay on the south side of La Crosse, WI. Our host, Amber, was great to work with and was super responsive to questions, etc. The kids really enjoyed the hot tub and dual living room areas. Having access to the garage space was another huge plus with the ice fishing gear we had to thaw out. The kitchen was well stocked with nice cookware and utensils - easy to find items and an abundance of space to prep meals! This place was by far the nicest we have ever stayed at! We highly recommend this rental and it would be great in the summer time as it has a really nice pool area and deck space!
A view from a balcony shows a lush, green landscape with rolling hills and a serene stream winding through the vegetation. The foreground features a fenced yard with well-maintained grass, bordered by trees and shrubs.
Farm stay in Chatfield
5 out of 5 average rating, 4 reviews

Lost Creek executive home on 200 acre horse ranch

TinaRating, 5 stars9 months ago
Tyler was a great host. He made things super easy and always responded. A tree went down during a storm and he had it cleared the same night. He allowed our kids to go up to the farm house to pet the horses and farm dogs. The house was very spacious and had plenty of room for 6 kids to run around. My son really like fishing in the stream and might have lost his crocs while he was fishing but over all great stay! I would recommend this house.

Other great vacation rentals in Winona

Guest favorite
A bright living area features a comfortable couch with yellow accents and a decorative area rug. Large windows allow natural light to fill the room, offering views of the surrounding greenery. Wall art adds a touch of color to the light-toned walls.
Barn in Hixton
4.9 out of 5 average rating, 279 reviews

A Suite Getaway

HodaRating, 5 stars2 weeks ago
Beautiful place with a scenic, private and peaceful location. Loved grilling on the fire and hot tub under the stars was amazing and we loved petting and feeding Hunter 🤎 Melanie was very nice and accommodating and made the whole experience smooth and delightful.
Top guest favorite
A spacious man cave features a wooden ceiling and light-colored walls. A comfortable couch faces a large TV, while a poker table equipped with green felt is surrounded by several black chairs. Decorative antler mounts adorn the walls, adding rustic charm.
Home in Arcadia
5 out of 5 average rating, 12 reviews

Arcadia Cottage

MariaRating, 5 stars3 days ago
If I come to Arcadia again I will love to stay at her place again, very responsive and helpful. Very understanding and flexible had to add more nights and she was quick to reply :) definitely recommend staying here! Thanks Christine
Superhost
The interior space features a wooden staircase leading to an open living area. Natural light fills the room through large windows, highlighting a seating area with couch and chairs. The kitchen and dining space are visible in the background, creating a welcoming environment.
Home in Rochester
4.75 out of 5 average rating, 8 reviews

Cozy tranquility 6mi from Mayo 4bed/3bath

KimberlyRating, 5 stars3 months ago
Clean and neat house in family neighborhood. Fenced in backyard which is nice because we had kids that wanted to play in snow. Easy drive to Mayo Clinic for appointments
Guest favorite
A modern kitchen features wooden cabinetry and a spacious island with three stools. Stainless steel appliances are neatly arranged, while flowers in a vase add a touch of color. Ample counter space is available for food preparation and cooking.
Home in Blair
4.97 out of 5 average rating, 31 reviews

Med Park House

MariaRating, 5 stars2 days ago
Very nice place to stay ! Glen and wife really nice people, they reply to you right away. Very nice clean homey I would recommend staying here ! Thank yu glen and wife
Guest favorite
A calm lake is visible under a twilight sky, with soft hues of pink and purple reflecting on the water's surface. Lush greenery frames the scene, highlighted by silhouettes of trees at the water's edge.
Cottage in Pepin
4.85 out of 5 average rating, 74 reviews

Scenic View Cottage on the Great River Road

KariRating, 5 stars7 months ago
We enjoyed our stay in Pepin. Charlie's cottage was close to everything we were interested in, was very quiet even though off the highway and we appreciated the accommodations.
Guest favorite
A single-story home is shown with a white exterior, featuring large windows and a welcoming front door. A well-maintained lawn with freshly mowed grass surrounds the house, complemented by a flowering tree nearby. A white picket fence encloses the yard.
Home in La Crosse
4.93 out of 5 average rating, 44 reviews

Comfortable, Hyde Away Home

KimberleeRating, 5 stars4 days ago
The place was exactly what I was hoping for. We were having a celebration of life and the kitchen enabled me to make all the food with no problem. It was furnished with all the cooking appliances, pot & pan & utensils that I needed. It was a very cute and cozy house. It was close the our event. Would definitely stay there again
Top guest favorite
An inviting game room features a ping pong table, foosball setup, and a retro arcade game. A comfortable seating area with two chairs is positioned beside a wall-mounted television, displaying vibrant graphics. Natural light filters in through large windows, enhancing the playful atmosphere.
Cabin in Alma Center
4.93 out of 5 average rating, 14 reviews

Whispering Pines/170-Acre Retreat-Pond & Game Room

RahmaRating, 5 stars4 days ago
The cabin we stayed in(Whispering Pines/Alma Center )was perfect for our group with kids. There were plenty of rooms and beds for everyone to sleep. All necessary cooking utensils were there. Shampoo, conditioner, and body wash in each bathroom, and plenty of towels.The game room was nice expirience.We spent majority of our time outdoors in beautiful nature. The hosts were very responsive and accomidating. Highly recommend staying here.
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

EmilyRating, 5 stars3 weeks ago
the Backwaters Lodge was the perfect place for our trip. It was my companion’s first time in Wisconsin and he got the most perfect representation of it at this place. The host, Dan, was excellent! Made sure we had everything we needed and was always one text away if we needed him! We will absolutely book this place again.

Quick stats about vacation rentals in Winona

  • Total rentals

    80 properties

  • Nightly prices starting at

    $20 before taxes and fees

  • Total number of reviews

    8.7K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Winona?

    Yes! Work meets play with ease at over 30 vacation rentals in Winona featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Winona?

    Four-legged friends are welcome in Winona. Choose from more than 10 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in house rentals in Winona?

    Experience the best of Winona with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Winona have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Winona. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winona have self check-in?

    Absolutely! We offer over 10 house rentals with self check-in in Winona. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Winona?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with self check-in, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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