Search Holiday Rentals in Winona

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Top Holiday Rentals in Winona

Greenwood Studio Cottage < 1 Mi to Downtown!

3.5 star property
6.8 out of 10, (3)
"Every thing was great except the bed mattress was very uncomfortable, and the door to the bathroom was sticking when you open and closed it. Overall iitwas an excellent stay,"
Greenwood Studio Cottage < 1 Mi to Downtown!

Modern Greenwood Studio < 1 Mi to Downtown!

3.0 star property
Modern Greenwood Studio < 1 Mi to Downtown!

Homey Greenwood Getaway w/ Patio & Backyard

3.0 star property
Homey Greenwood Getaway w/ Patio & Backyard

Updated Greenwood Cottage Apt < 1 Mi to Dtwn!

3.0 star property
10.0 out of 10, Exceptional, (2)
"We can't say enough positive about the property and especially the manager/owner. The property is an updated apartment for sure. Clean, well equipped, and spacious. She texted us twice in our four night stay to make sure everything was going well. We highly recommend this property!!! Thank you!!"
Updated Greenwood Cottage Apt < 1 Mi to Dtwn!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

Are there holiday rentals in Winona?

Yes, there are holiday rentals close to the most popular sights in Winona, or you can select a more secluded option if you're looking for a relaxing stay. Winona is known for its coffee shops and baseball games. Make sure you have time to check out the restaurants while you're in the area.

What can I see and do in Winona?

Take time out to visit local sights such as Montgomery County Performing Arts Center, Winona Country Club, and Winona - Montgomery County Library. In the wider area, you’ll find Winona City Hall and Middleton Cemetery.

What are holiday rentals like in Winona?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winona. Holiday rentals feature extras such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family trip.