Photo by Jessica Richter

Winona Holiday Rentals

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Holiday Rentals in Winona

Holiday Home in Van Buren

2.0 star property
9.0 out of 10, Wonderful, (15)
"It was beautiful and homey. We really enjoyed our stay. "
United States
Jessica
The price is AU$259
includes taxes & fees
4 Dec - 5 Dec
Charming 2-bedroom house with AC, WiFi in serene Van Buren

Cabin in Piedmont

10.0 out of 10, Exceptional, (33)
"Beautiful property, I’d recommend to anyone going here to stay here."
United States
tom
The price is AU$208
includes taxes & fees
4 Dec - 5 Dec
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock

Cabin in Alton

10.0 out of 10, Exceptional, (16)
"Beautiful property, lots of fun stuff to do. Wild life was really cool, and the sky at night is insane. Can’t wait to come back next year for our eleven point trip!"
United States
Anonymous traveller
The price is AU$356
includes taxes & fees
3 Jan - 4 Jan 2026
Quiet 2 story Cabin on 32 acres near eleven point river

Cabin in Van Buren

9.4 out of 10, Exceptional, (3)
"Beautiful property. Would stay again."
United States
Sharon P.
The price is AU$398
includes taxes & fees
10 Dec - 11 Dec
Hilltop House #2

Apartment in Van Buren

10.0 out of 10, Exceptional, (2)
"The property was clean and comfortable. It had everything we needed for a weekend stay innVan Buren."
United States
Tara W.
The price is AU$343
includes taxes & fees
15 Dec - 16 Dec
Easy Street Apartment

Apartment in Van Buren

10.0 out of 10, Exceptional, (3)
"The cutest place to stay after a long day on the river! Natalie was great, and the place was very clean and comfortable."
United States
Krista M.
The price is AU$343
includes taxes & fees
4 Dec - 5 Dec
Cozy Corner

Cabin in Van Buren

2.0 star property
The price is AU$217
includes taxes & fees
4 Dec - 5 Dec
Cozy quiet country getaway just minutes from the Current River

Cabin in Summersville

10.0 out of 10, Exceptional, (70)
"Wanted an escape before starting back to school for the fall and this was exactly what we got. Easy communication with owner and got quick response. Beautiful and quiet property! Great spot on the river!"
United States
Erin A.
The price is AU$522
includes taxes & fees
7 Dec - 8 Dec
#ContemplationCabin on the Jacks Fork River!

Holiday Home in Birch Tree

10.0 out of 10, Exceptional, (21)
"Place was perfect for our stay. Beautiful property. "
United States
Drew W.
The price is AU$417
includes taxes & fees
2 Jan - 3 Jan 2026
Newly renovated early 1900’s farmhouse

Holiday Home in Van Buren

2.0 star property
The price is AU$306
includes taxes & fees
14 Dec - 15 Dec
Family-Friendly 3BR/2BA Van Buren Home w/ Fire Pit & Starlink WiFi!

Holiday Home in Mountain View

The price is AU$455
includes taxes & fees
10 Dec - 11 Dec
Newly renovated family/pet-friendly Mountain View home

Holiday Home in Eminence

9.4 out of 10, Exceptional, (18)
"Would stay here again. Description accurate, easy to find, clean, no contact check-in, owner quick to respond. "
United States
dottie c.
The price is AU$370
includes taxes & fees
31 Dec - 1 Jan 2026
Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride

Holiday Home in Van Buren

2.0 star property
10.0 out of 10, Exceptional, (10)
"Wonderful stay. Good location. Very enjoyable experience."
United States
Thomas H.
The price is AU$873
includes taxes & fees
11 Dec - 12 Dec
Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12

Cabin in Van Buren

10.0 out of 10, Exceptional, (1)
"Absolutely perfect in every way, beautiful view! Host were very kind and helpful!!"
United States
Loretta B.
The price is AU$528
includes taxes & fees
14 Dec - 15 Dec
Hilltop House #1 with AMAZING views
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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Top Winona Hotel Reviews

Find out more about Winona

Everything you need to know about Winona holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winona holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winona holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winona holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winona. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winona holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona holiday rentals we have selected for you start as low as AU$208 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winona rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winona holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winona. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

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