A river surrounded by dense green forest.

Winona Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Winona vacation rentals

Property grounds

1. Hogan's Hideout Cottage #8

Hogan's Hideout Cottage #8
Eminence
8.0 out of 10, Very Good, (3 reviews)
"Nice private and rustic"
United States
Anonymous traveler
The price is SAR 544
SAR 832 total
includes taxes & fees
18 Aug - 19 Aug
Hogan's Hideout Cottage #8
Outdoor spa tub

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 SAR 605
SAR 1,038 total
includes taxes & fees
16 Aug - 17 Aug
Bungalow with Hot Tub in Birch Tree
Coffee/tea maker, fridge, microwave, oven

3. 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 SAR 605
SAR 1,083 total
includes taxes & fees
16 Aug - 17 Aug
Newly renovated early 1900’s farmhouse
Exterior

4. The Western

The Western
Eminence
9.4 out of 10, Exceptional, (3 reviews)
"This was an adorable and clean little place to stay, we enjoyed the hot tub also as a bonus!"
United States
Misty C.
The price is SAR 556
SAR 690 total
includes taxes & fees
24 Aug - 25 Aug
The Western
Interior

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, (25 reviews)
"Very convenient location for us. The cabin is perfect for two people. "
United States
Cynthia A. S.
The price is SAR 574
SAR 867 total
includes taxes & fees
19 Aug - 20 Aug
Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride
Exterior

6. Hogan's Hideout Cottage #7

Hogan's Hideout Cottage #7
Eminence
9.0 out of 10, Wonderful, (12 reviews)
"Very helpful with anything we needed!"
United States
Janice
The price is SAR 544
SAR 836 total
includes taxes & fees
16 Aug - 17 Aug
Hogan's Hideout Cottage #7
Exterior

7. 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 SAR 544
SAR 804 total
includes taxes & fees
19 Aug - 20 Aug
Hogan's Hideout Cozy Cottage #5
Property grounds

8. 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 SAR 939
SAR 1,287 total
includes taxes & fees
6 Sep - 7 Sep
New cabin located on the jacks fork river front.
WiFi

9. Cozy Corner

Cozy Corner
Van Buren
9.8 out of 10, Exceptional, (6 reviews)
"Host was amazing and extremely responsive!! Close to everything we wanted to do"
United States
Dierdre
The price is SAR 559
SAR 899 total
includes taxes & fees
17 Aug - 18 Aug
Cozy Corner
Exterior

10. 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 SAR 574
SAR 919 total
includes taxes & fees
17 Aug - 18 Aug
Easy Street Apartment
House (3 Bedrooms) | Interior

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

Home Near Eleven Point River & Nat'l Forest!
3.0 star property
Alton
The price is SAR 436
SAR 773 total
includes taxes & fees
16 Aug - 17 Aug
Home Near Eleven Point River & Nat'l Forest!
Interior

12. 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
9.4 out of 10, Exceptional, (8 reviews)
"Perfect spot to get away with the family!"
United States
Jennifer P.
The price is SAR 657
SAR 1,025 total
includes taxes & fees
8 Sep - 9 Sep
Family-Friendly 3BR/2BA Van Buren Home w/ Fire Pit & Starlink WiFi!
Outdoor dining

13. 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, (21 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 SAR 428
SAR 859 total
includes taxes & fees
17 Aug - 18 Aug
Quiet 2 story Cabin on 32 acres near eleven point river
Private kitchen

14. White Family Suite

White Family Suite
Eminence
The price is SAR 1,055
SAR 1,769 total
includes taxes & fees
8 Sep - 9 Sep
White Family Suite
Coffee/tea maker, fridge, microwave, stovetop

15. 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 SAR 297
SAR 769 total
includes taxes & fees
16 Aug - 17 Aug
Home Near Eleven Point River & Nat'l Forest!
Microwave, stovetop

16. 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 SAR 571
SAR 684 total
includes taxes & fees
8 Sep - 9 Sep
Nice 2-bedroom cottage with AC in Mountain View
Property grounds

17. #ContemplationCabin on the Jacks Fork River!

#ContemplationCabin on the Jacks Fork River!
Summersville
10.0 out of 10, Exceptional, (82 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 SAR 939
SAR 1,348 total
includes taxes & fees
7 Sep - 8 Sep
#ContemplationCabin on the Jacks Fork River!
Coffee/tea maker, fridge, microwave, oven

18. 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, (43 reviews)
"Perfect cabin for a fishing trip. My Dad and I loved staying there."
United States
Anonymous traveler
The price is SAR 451
SAR 551 total
includes taxes & fees
14 Aug - 15 Aug
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock
Terrace/patio

19. 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, (16 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 SAR 1,183
SAR 2,203 total
includes taxes & fees
19 Aug - 20 Aug
Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12
Private kitchen

20. Peaceful Stay Near Current River

Peaceful Stay Near Current River
Van Buren
10.0 out of 10, Exceptional, (2 reviews)
"In Van Buren for a family reunion. The house fit the needs for 2 couples, or more. Master bedroom and bath are large, the 2 other bedrooms are ok in size. We used the extra bedroom for our suitcases, which worked out great. Spacious and stocked kitchen. Plenty of towels, and bathrooms were supplied nicely. Enjoyed sitting under the covered drive with coffee in the morning rain. We would certainly stay here again. A few things…the kitchen garbage can was half full on arrival (odd). The king...
United States
Rebecca S.
The price is SAR 1,108
SAR 1,819 total
includes taxes & fees
16 Aug - 17 Aug
Peaceful Stay Near Current River
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winona Hotel Reviews

Cozy Riverfront Cabin on the Current River. Relax, Unwind & Explore the Ozarks

Cozy Riverfront Cabin on the Current River. Relax, Unwind & Explore the Ozarks

10/10 Excellent
"Great place, comfortable, kitchen is stocked with all the pots, pans, and utensils you'll need. Big yard with clover, deer come around at night. Big deck with a great view of the river or the stars/meteors at night. River is beautiful, lots of amazing springs nearby, and Rocky Falls is an excellent place to swim.There are a few nails sticking up on the deck, including on the stairs coming up. No biggie, but you'll want to be careful walking barefooted until those are fixed.And there's a surprisingly large grocery store in Van Buren if you run out of food like we did, haha. They're open relatively late too."
Matthew B. 5-night trip
Posted 1 day ago
Cozy Riverfront Cabin on the Current River. Relax, Unwind & Explore the Ozarks

Frequently asked questions

Are there vacation rentals in Winona?

Yes, we give you a choice of vacation rentals near the most popular attractions in Winona, or you can select a more remote option if you're looking for a relaxing stay.

What's the top vacation rental in Winona?

Unique cabins in the woods
Not friendly for Street Bikes. : Visitors like this Winona vacation home rental. It is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 vacation rental in Winona like?

Vacation rentals are private properties you can stay in for short or long periods in Winona. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for families.