
Vacation rentals in Winona
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Top-rated vacation rentals in Winona
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Winona vacation rentals
Vacation rentals with pools in Winona

MINNeSTAY* Riverfront Inn | Hot tub
This property is utterly blissful! The home is luxurious, comfortable, and fully stocked with thoughtful amenities. Every surface, inside and out, was sparkling clean and well cared for. The property is serenely beautiful, and the views will take your breath away. The pool was the finest of any Airbnb pool we have ever had the pleasure of enjoying: pristine, well heated, and meticulously cared for by a kind gentleman who went above and beyond to ensure perfection. The sunsets over the fire pit are priceless. Correspondence with the host was immediate, helpful, and friendly. We are verklempt! Thank you sincerely for sharing this treasure with us!

Bear Creek Lodge w/ Pool and Hot Tub
We had a great stay. Host was very responsive and sent clear instructions for checkin. Location was really good for a family reunion we were attending in Caledonia, MN. Whiel the house is on a highway next to a motel, it was very private and quiet in the house. House has 3 bedrooms (each with a queen size bed) as well as a basement with 2 queen beds, so there was plenty of room for all of us. Most of the house was very clean and neat. There were a ton of amenities and the kitchen was very well stocked. The only bad thing was that someone had put away dirty dishes in the cupboards and drawers. Since the guest is supposed to clean all dishes and put them away before leaving, I am assuming that the previous guests did this. However, the cleaners should probably check for this. I would stay here again if visitng relatives in MN.

The Log Cabin @UpperIowaResort
This was a relaxing stay with a beautiful cabin along the river. It was way from commotion, with the fun sand bottom swimming area for kids plus fishing in the river or canoeing down the river.

3 Bedroom home (sleeps 8)
we loved our stay! the pool was incredible and the house was gorgeous and VERY comfortable!!

Come unwind with us at Kindred Tiny House.
A beautiful, quiet location that's only minutes from town and some nice hiking locations. For anyone wondering about privacy, the big windows have screens, and the neighbors aren't right up next to the unit. I mostly used the screens for heat control :) Natalie was a friendly and helpful host, and the space was comfortable. I'd happily stay here again!

RARE! Pool, hot tub, garden &chickens! 4m to Mayo
Tiffany was extremely responsive and communicated very well! The home was beautiful, especially with the outdoor views. Such a great place to stay at.

Unit 2365J | 2bd/2bth | Single-Family Home
For an extended stay, this home fits the bill. It is in a very handy location with restaurants, grocery stores, gas stations, etc., only a few blocks away. The home is new & in a new area, where the properties are nice , very well maintained & managed. Allison, our coordinator did a very good job of answering our questions any time we called her . If available, we would definitely stay there again should we ever need an extended stay in Rochester.

Cozy, quiet place w/pool/hot tub
Perfect home for a larger family or group! We really enjoyed our time at Mindy’s home. There was plenty of space for everyone and the pool and hot tub were bonuses! We were in town for a wedding and Mindy was very flexible with check-in and very responsive and kind. Beautiful location with a ballpark right across the street. Highly recommended, Thank you!
Other great vacation rentals in Winona

Our Little River House
This was the perfect little gem!! House had a beautiful view of the river and bluffs, right in the heart of Fountain City. The house was super clean, had everything we needed, and the added bonus was that the floors must have been very well insulated because putting our babies to bed upstairs, you couldn’t hear anything happening downstairs! There was a private back yard for our dog to run around in as well which was perfect. Would definitely recommend and I hope to return!

Ridgetop Retreat
The Ridgetop Retreat was just what was promised. It was clean, comfortable and cozy. only thing I'd note, the sun comes up and shines right in the windows so, if you like to sleep in at all, bring a sleep mask!

The Driftless House - Winona, MN
The house was above what was described in words and pictures Celeste was great to work with. Very responsive and flexible Would recommend this property to anyone.

A Stone's Throw Bungalow
Megan was such a friendly and responsive host, and her home was the perfect place for my kiddos and me to stay when we were visiting family in Winona! The home has a beautiful, big fenced-in yard with plenty of grass to play in, all of the amenities that we needed, including smart TVs, all of the kitchen appliances we wanted, games and puzzles, and a nice long driveway. It’d also located just across the street from the lake, which is really convenient and so lovely! All of Megan’s amazing photography lining the walls is an added bonus :) We can’t wait to stay here again the next time we’re in town. Thanks, Megan, for giving my crew such a cozy and comfortable place to land!

Driftless Blufftop Hike-in Outdoor Bed - Celtis
This was a beautiful stay. The hike up was worth it! The area was peaceful and all the listed amenities were great. We enjoyed the Memorial Day weekend additional amenities! Highly recommend for being outdoors without the hassle of setting up camping equipment. The Celtis campsite is perfect.

The Village House Inn
This is the second time we have stayed at this house (refer to my previous review from May-June 2024). It is a great house in a nice quiet area. We really appreciate how every room has its own bathroom, which is nice when you have a larger group of guys like we do. We have nothing but good things to say about the house as well as the host, as Samantha is very nice, responsive, and easy to work with. She was also very flexible with us and took care of us as return customers. At the moment we do not plan to return to Winona next year, but if we ever do come out this way again, we will certainly be staying here again!

The Exchange 14 | Historic Bldg, Studio, Dwntwn
Had such a lovely stay here, it's super close and local to everything you need. The building is lovely and bed is very comfy! Host was amazing and super flexible and accommodating for my last minute extended stay. Would highly recommend staying here anytime and will definitely be back!

Fountain City Loft, hot tub, river views
We have a great stay. Brad was very responsive to any questions we had. Thank you.
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 apartment rentals in Winona?
Experience the best of Winona with our apartment rentals, starting at about $60 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 a bbq area, over 10 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.
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