Photo by Jessica Richter

Holiday Rentals in Winona

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Winona

Charming 2-bedroom house with AC, WiFi in serene Van Buren

2.0 star property
8.6 out of 10, Excellent, (7)
"The place was cozy. Everything worked. The amenities were plenty. We decided to take a day trip, never been to the area and we couldn’t have picked a more perfect place to stay, especially during the busy months you get to avoid the more touristy spots and stay in a very comfortable secluded space."
The price is €142
includes taxes & fees
16 Jul - 17 Jul
Charming 2-bedroom house with AC, WiFi in serene Van Buren

Cozy Studio

9.0 out of 10, Wonderful, (9)
"There were a few issues but Jessica took care of them. Thank you Jessica!"
The price is €108
includes taxes & fees
16 Jul - 17 Jul
Cozy Studio

Newly renovated early 1900’s farmhouse

10.0 out of 10, Exceptional, (16)
"Great little house. "
The price is €258
includes taxes & fees
16 Jul - 17 Jul
Newly renovated early 1900’s farmhouse

Hilltop House #1 with AMAZING views

The price is €303
includes taxes & fees
22 Jul - 23 Jul
Hilltop House #1 with AMAZING views

Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12

2.0 star property
10.0 out of 10, Exceptional, (3)
"Perfect location and beautiful house"
The price is €500
includes taxes & fees
17 Jul - 18 Jul
Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12

Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride

9.2 out of 10, Wonderful, (11)
"Decent place, lots of ladybugs in the house!"
Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride
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.
Save an average of 15% on thousands of hotels when you're signed in

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.

What are some of the best holiday rentals that Winona has to offer?

Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!: This highly rated holiday home rental in Winona is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

What’s there to see and do in Winona?

Rocky Falls and Ozark National Scenic Riverways are a couple of lovely local spots to get outside and enjoy nature. While here, Mark Twain National Forest and Current River are other places worth a visit.

What’s a holiday rental in Winona like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winona. Holiday rentals offer amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family trip or a small group gathering.