
Vacation rentals in Winona
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Winona
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winona vacation rentals
Vacation rentals with pools in Winona

Brand New, 3 Bed/ 2 Bath w/ Parking on UWL Campus
Cute house in a great location on campus!

Come unwind with us at Kindred Tiny House.
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!

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

The Lodge at Heart & Soil Ridge
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!

Cozy, quiet place w/pool/hot tub
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.

The Shack
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.

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

Lost Creek executive home on 200 acre horse ranch
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

A Suite Getaway
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.

Arcadia Cottage
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

Cozy tranquility 6mi from Mayo 4bed/3bath
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

Med Park House
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

Scenic View Cottage on the Great River Road
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.

Comfortable, Hyde Away Home
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

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

Backwaters lodge
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
- Wisconsin River Vacation rentals
- Wisconsin Dells Vacation rentals
- Twin Cities Vacation rentals
- Saint Paul Vacation rentals
- Rochester Vacation rentals
- La Crosse Vacation rentals
- Bloomington Vacation rentals
- Eau Claire Vacation rentals
- Decorah Vacation rentals
- Stillwater Vacation rentals
- Lake Delton Vacation rentals
- Chicago Vacation rentals
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes