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Holiday Rentals in Winona

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Our top choices for Winona holiday rentals

“The Cabin”@ Serenity Ranch. Centrally located to all the wonders of Shannon co.

“The Cabin”@ Serenity Ranch. Centrally located to all the wonders of Shannon co.
Winona
10.0 out of 10, Exceptional, (16)
"This property is beautiful. It had everything we needed to enjoy our stay. I would highly recommend this cabin. So cute."
United States
Ruth B.
“The Cabin”@ Serenity Ranch. Centrally located to all the wonders of Shannon co.

Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!

Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!
Eminence
10.0 out of 10, Exceptional, (75)
"The house and property is wonderful. The game room in the garage was a lot of fun. The house was very clean. Close to town, but still incredibly peaceful.We hope to stay again. "
United States
Lillie P.
Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!

#ContemplationCabin on the Jacks Fork River!

#ContemplationCabin on the Jacks Fork River!
Summersville
10.0 out of 10, Exceptional, (72)
"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 €296
includes taxes & fees
17 Dec - 18 Dec
#ContemplationCabin on the Jacks Fork River!

Cozy Cabin on the edge of town only 1/2 mile from Current River !

Cozy Cabin on the edge of town only 1/2 mile from Current River !
Van Buren
9.4 out of 10, Exceptional, (8)
"We stay here a couple times a year. In the summer to float the river and in the winter to be near relatives for the holidays. Great experience in both seasons. Very close to the river, gas, and grocery. "
United States
Shelie L.
Cozy Cabin on the edge of town only 1/2 mile from Current River !

Kings Cabin on the edge of town only 1/2 mile from Current River !

Kings Cabin on the edge of town only 1/2 mile from Current River !
Van Buren
9.2 out of 10, Wonderful, (28)
"Nice quiet area"
United States
Tonya F.
Kings Cabin on the edge of town only 1/2 mile from Current River !

Springside Cottage in beautiful Eminence. Great outdoor space - NEW Hot tub!

Springside Cottage in beautiful Eminence. Great outdoor space - NEW Hot tub!
Eminence
9.2 out of 10, Wonderful, (15)
"Very nice place to stay"
United States
Beth S.
Springside Cottage in beautiful Eminence. Great outdoor space - NEW Hot tub!

Fox Pen Cabins Cabin #2 Not friendly for street bikes… Pet-Friendly

Fox Pen Cabins Cabin #2 Not friendly for street bikes… Pet-Friendly
3.0 star property
Eminence
9.2 out of 10, Wonderful, (10)
"Great little cabin, roads to cabin not the best but worth it!"
United States
Pam
Fox Pen Cabins Cabin #2 Not friendly for street bikes… Pet-Friendly

Charming Bunk House Suite in Eminence with AC/Heat, Kitchenette & full bath

Charming Bunk House Suite in Eminence with AC/Heat, Kitchenette & full bath
Eminence
9.6 out of 10, Exceptional, (5)
"It was a very nice place and quiet area definitely going back another time. "
United States
Emily D.
Charming Bunk House Suite in Eminence with AC/Heat, Kitchenette & full bath

Unbeatable convenience in amazing Eminence!

Unbeatable convenience in amazing Eminence!
Eminence
10.0 out of 10, Exceptional, (18)
"Excellent stay place was well kept and clean and had everything we could’ve needed "
United States
Jeremy B.
Unbeatable convenience in amazing Eminence!

Triple H Properties

Triple H Properties
Eminence
8.6 out of 10, Excellent, (27)
"Worked out great for friends to stay for a float trip weekend. "
United States
Kat S.
Triple H Properties

Chasen Summer! 1/2 Mile from Current River!

Chasen Summer! 1/2 Mile from Current River!
Van Buren
9.4 out of 10, Exceptional, (40)
"My Family and I have stayed at this house "
United States
Benjamin D.
Chasen Summer! 1/2 Mile from Current River!

Deadwood Acres cabin #1

Deadwood Acres cabin #1
Eminence
9.8 out of 10, Exceptional, (52)
"Nice quiet cabin"
United States
James H.
Deadwood Acres cabin #1

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

Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride
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 €210
includes taxes & fees
31 Dec - 1 Jan 2026
Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride

Deadwood Acres cabin #2

Deadwood Acres cabin #2
Eminence
9.8 out of 10, Exceptional, (38)
"We loved it, the owners were great, love the little cabin,it had everything we need, we will be going back"
United States
sammie m.
Deadwood Acres cabin #2

The Cabin on Current River with Private Gravel Bar!!

The Cabin on Current River with Private Gravel Bar!!
Van Buren
8.8 out of 10, Excellent, (28)
"Beautiful area, secluded. We enjoyed staying at this property and access to the river was as expected."
United States
Anonymous traveller
The Cabin on Current River with Private Gravel Bar!!

Clearwater Lake, cabin minutes from Bluff View Marina & boat dock

Clearwater Lake, cabin minutes from Bluff View Marina & boat dock
Piedmont
10.0 out of 10, Exceptional, (34)
"Beautiful property, I’d recommend to anyone going here to stay here."
United States
tom
The price is €119
includes taxes & fees
16 Dec - 17 Dec
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock

Family-friendly Cabin w/150 ft Current River frontage in Ozark Scenic River

Family-friendly Cabin w/150 ft Current River frontage in Ozark Scenic River
Van Buren
9.6 out of 10, Exceptional, (57)
"Beautiful property on the current. Had a wonderful Time would definitely stay here again "
United States
Tiler P.
Family-friendly Cabin w/150 ft Current River frontage in Ozark Scenic River

Secluded Ozarks Tiny House cabin in Eminence, MO at Old Desperado Ranch

Secluded Ozarks Tiny House cabin in Eminence, MO at Old Desperado Ranch
Eminence
9.6 out of 10, Exceptional, (103)
"We had so much fun. The hosts were amazing. The food at the whiskey river outpost was delicious. My kids loved the tiny house so much that they wanted to buy it and bring it home with us so we could live in it. "
United States
Alicia J.
Secluded Ozarks Tiny House cabin in Eminence, MO at Old Desperado Ranch

Family-Friendly 3BR/2BA Van Buren Home w/ Fire Pit & Starlink WiFi!

Family-Friendly 3BR/2BA Van Buren Home w/ Fire Pit & Starlink WiFi!
2.0 star property
Van Buren
The price is €175
includes taxes & fees
16 Dec - 17 Dec
Family-Friendly 3BR/2BA Van Buren Home w/ Fire Pit & Starlink WiFi!

Rustic charm with modern amenities, ensuring a comfortable and memorable stay.

Rustic charm with modern amenities, ensuring a comfortable and memorable stay.
Mountain View
10.0 out of 10, Exceptional, (10)
"Our host, Tish, was absolutely wonderful and so accommodating! We will definitely stay there for the next vacation out that way!!"
United States
chanelle e.
Rustic charm with modern amenities, ensuring a comfortable and memorable stay.
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, apart-hotels, 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 favorite 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 depends 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 €119 per night. Entering your travel dates in the search wizard you might find 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.