A river surrounded by dense green forest.

Winona Holiday Rentals

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Our top choices for Winona holiday rentals

1. Newly renovated early 1900’s farmhouse

Newly renovated early 1900’s farmhouse
Birch Tree
10.0 out of 10, Exceptional, (28 reviews)
"One of the best places I have ever stayed! Marsha was a wonderful host! "
United States
Devon J.
The price is NZ$500
includes taxes & fees
1 Sept - 2 Sept
Newly renovated early 1900’s farmhouse

2. Bungalow with Hot Tub in Birch Tree

Bungalow with Hot Tub in Birch Tree
Birch Tree
10.0 out of 10, Exceptional, (5 reviews)
The price is NZ$480
includes taxes & fees
1 Sept - 2 Sept
Bungalow with Hot Tub in Birch Tree

3. Hogan's Hideout Cozy Cottage #5

Hogan's Hideout Cozy Cottage #5
Eminence
9.8 out of 10, Exceptional, (7 reviews)
"The cabin was clean and had everything we needed. We did not spend a lot of time there during the day but it was just what we needed, especially with the heat! The A/C unit worked great. "
United States
Shawna C.
The price is NZ$358
includes taxes & fees
1 Sept - 2 Sept
Hogan's Hideout Cozy Cottage #5

4. New cabin located on the jacks fork river front.

New cabin located on the jacks fork river front.
Eminence
8.8 out of 10, Excellent, (15 reviews)
"Great location"
United States
Trent B.
The price is NZ$568
includes taxes & fees
7 Sept - 8 Sept
New cabin located on the jacks fork river front.

5. 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
9.6 out of 10, Exceptional, (27 reviews)
"Nice little place. Great amenities. Great host. Perfect for a weekend getaway to kayak and hike."
United States
Kent L.
The price is NZ$386
includes taxes & fees
1 Sept - 2 Sept
Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride

6. The Western

The Western
Eminence
9.6 out of 10, Exceptional, (7 reviews)
"Cute decor, comfortable beds, covered patio with grill and clean hot tub!"
United States
Robert
The price is NZ$255
includes taxes & fees
6 Sept - 7 Sept
The Western

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

Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12
Van Buren
10.0 out of 10, Exceptional, (17 reviews)
"Amazing place for our crew of 7 adults and 6 kids to stay. Everything was clean and perfectly located for exploring current river."
United States
Dillion
The price is NZ$982
includes taxes & fees
1 Sept - 2 Sept
Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12

8. Peaceful Stay Near Current River

Peaceful Stay Near Current River
Van Buren
10.0 out of 10, Exceptional, (4 reviews)
"We had a great stay at this house! Super clean, and easy find! Will definitely stay here again!"
United States
Danni H.
The price is NZ$872
includes taxes & fees
1 Sept - 2 Sept
Peaceful Stay Near Current River

9. White Family Suite

White Family Suite
Eminence
The price is NZ$774
includes taxes & fees
10 Sept - 11 Sept
White Family Suite

10. Cozy Corner

Cozy Corner
Van Buren
9.8 out of 10, Exceptional, (8 reviews)
"Host was amazing and extremely responsive!! Close to everything we wanted to do"
United States
Dierdre
The price is NZ$400
includes taxes & fees
1 Sept - 2 Sept
Cozy Corner

11. #ContemplationCabin on the Jacks Fork River!

#ContemplationCabin on the Jacks Fork River!
Summersville
10.0 out of 10, Exceptional, (84 reviews)
"Cabin was clean and cosy. Took a little bit of patience to get the fire going but it warmed up the cabin quite nicely once going."
United States
Teagan B.
The price is NZ$603
includes taxes & fees
7 Sept - 8 Sept
#ContemplationCabin on the Jacks Fork River!

12. Hogan's Hideout Cottage #8

Hogan's Hideout Cottage #8
Eminence
8.0 out of 10, Very good, (4 reviews)
"Nice private and rustic"
United States
Anonymous traveller
The price is NZ$371
includes taxes & fees
1 Sept - 2 Sept
Hogan's Hideout Cottage #8

13. Hogan's Hideout Cottage #7

Hogan's Hideout Cottage #7
Eminence
8.6 out of 10, Excellent, (14 reviews)
"Very helpful with anything we needed!"
United States
Janice
The price is NZ$371
includes taxes & fees
1 Sept - 2 Sept
Hogan's Hideout Cottage #7

14. Easy Street Apartment

Easy Street Apartment
Van Buren
10.0 out of 10, Exceptional, (3 reviews)
"The property was clean and comfortable. It had everything we needed for a weekend stay innVan Buren."
United States
Tara W.
The price is NZ$400
includes taxes & fees
1 Sept - 2 Sept
Easy Street Apartment

15. Home Near Eleven Point River & Nat'l Forest!

Home Near Eleven Point River & Nat'l Forest!
3.0 star property
Alton
The price is NZ$348
includes taxes & fees
4 Sept - 5 Sept
Home Near Eleven Point River & Nat'l Forest!

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

Family-Friendly 3BR/2BA Van Buren Home w/ Fire Pit & Starlink WiFi!
Van Buren
9.0 out of 10, Wonderful, (10 reviews)
"Perfect spot to get away with the family!"
United States
Jennifer P.
The price is NZ$422
includes taxes & fees
1 Sept - 2 Sept
Family-Friendly 3BR/2BA Van Buren Home w/ Fire Pit & Starlink WiFi!

17. Quiet 2 story Cabin on 32 acres near eleven point river

Quiet 2 story Cabin on 32 acres near eleven point river
Alton
10.0 out of 10, Exceptional, (23 reviews)
"This was one of the best trips we’ve ever had! The cabin was beautiful and stocked with so many nice surprises. We loved our stay!"
United States
Lisa B.
The price is NZ$382
includes taxes & fees
1 Sept - 2 Sept
Quiet 2 story Cabin on 32 acres near eleven point river

18. Nice 2-bedroom cottage with AC in Mountain View

Nice 2-bedroom cottage with AC in Mountain View
Mountain View
10.0 out of 10, Exceptional, (3 reviews)
"What a great, off the beaten path and away from people noise cabin. Wonderful views and very relaxing! Clean, new and comfortable. Will be back!"
United States
Deena P.
The price is NZ$282
includes taxes & fees
1 Sept - 2 Sept
Nice 2-bedroom cottage with AC in Mountain View

19. 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, (45 reviews)
"Would stay here again"
United States
Steve A.
The price is NZ$248
includes taxes & fees
1 Sept - 2 Sept
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock

20. Home Near Eleven Point River & Nat'l Forest!

Home Near Eleven Point River & Nat'l Forest!
Alton
7.0 out of 10, Good, (2 reviews)
"We had a great stay! The getaway was clean and inviting. Its super artsy and creative-just a really fun place. Amber and Marc were very informative. Any and all questions we had were answered. Everything was ready and available. Amber is super helpful and just a really great person. Will be back and highly recommend!!!"
United States
Amy
The price is NZ$348
includes taxes & fees
4 Sept - 5 Sept
Home Near Eleven Point River & Nat'l Forest!
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winona holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winona. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winona. Seeing all the best attractions is bound to make you fall in love with Winona. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winona short-term rentals, that won’t be hard to do.

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.