A river surrounded by dense green forest.

Winona Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winona vacation rentals

Coffee/tea maker, fridge, microwave, oven

1. Newly renovated early 1900’s farmhouse

Newly renovated early 1900’s farmhouse
Birch Tree
10.0 out of 10, Exceptional, (30 reviews)
"One of the best places I have ever stayed! Marsha was a wonderful host! "
United States
Devon J.
The price is AED 625
AED 1,098 total
includes taxes & fees
24 Sep - 25 Sep
Newly renovated early 1900’s farmhouse
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, (6 reviews)
"This is the best VRBO we have ever stayed at as a couple. Cute, clean and all the amenities plus more. House and outside activities was perfection in this small town but not too far away from local sites!"
United States
Christina V.
The price is AED 657
AED 1,094 total
includes taxes & fees
24 Sep - 25 Sep
Bungalow with Hot Tub in Birch Tree
Exterior

3. Hogan's Hideout Cottage #7

Hogan's Hideout Cottage #7
Eminence
8.8 out of 10, Excellent, (15 reviews)
"Very helpful with anything we needed!"
United States
Janice
The price is AED 533
AED 818 total
includes taxes & fees
24 Sep - 25 Sep
Hogan's Hideout Cottage #7
Smart TV

4. CountryComfortRetreat!!! 2-bedroom mobile home with AC in Birch Tree

CountryComfortRetreat!!! 2-bedroom mobile home with AC in Birch Tree
Birch Tree
9.6 out of 10, Exceptional, (5 reviews)
"Property is newly updated and well maintained. We came down to float Jacks k and didn't want to stay at a campground. This place is peaceful and away from town. Beds are comfortable, shower was warm, and house was cozy. The only thing to note is house is not centra air and bedrooms get hot. Host provides box fans however with doors closed room still stays warm."
United States
Kim R.
The price is AED 367
AED 539 total
includes taxes & fees
27 Sep - 28 Sep
CountryComfortRetreat!!! 2-bedroom mobile home with AC in Birch Tree
Property grounds

5. 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 weekend on the Jack's fork River. The cabin was exactly as advertised. Nice location, comfortable. No complaints."
United States
Amanda S.
The price is AED 918
AED 1,270 total
includes taxes & fees
24 Sep - 25 Sep
New cabin located on the jacks fork river front.
Interior

6. 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 AED 562
AED 849 total
includes taxes & fees
2 Oct - 3 Oct
Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride
Coffee/tea maker, fridge, microwave, stovetop

7. 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 AED 290
AED 760 total
includes taxes & fees
24 Sep - 25 Sep
Home Near Eleven Point River & Nat'l Forest!
Terrace/patio

8. 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, (19 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 AED 1,157
AED 2,155 total
includes taxes & fees
24 Sep - 25 Sep
Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12
House (3 Bedrooms) | Interior

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

Home Near Eleven Point River & Nat'l Forest!
3.0 star property
Alton
The price is AED 426
AED 756 total
includes taxes & fees
24 Sep - 25 Sep
Home Near Eleven Point River & Nat'l Forest!
Outdoor dining

10. Cozy quiet country getaway just minutes from the Current River

Cozy quiet country getaway just minutes from the Current River
Van Buren
10.0 out of 10, Exceptional, (5 reviews)
"Great little place"
United States
Nancy C.
The price is AED 496
AED 771 total
includes taxes & fees
24 Sep - 25 Sep
Cozy quiet country getaway just minutes from the Current River
Exterior

11. 3-bedroom/2 bath house in Van Buren MO located on the Current River

3-bedroom/2 bath house in Van Buren MO located on the Current River
Van Buren
The price is AED 826
AED 1,882 total
includes taxes & fees
24 Sep - 25 Sep
3-bedroom/2 bath house in Van Buren MO located on the Current River
Private kitchen

12. 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 AED 1,194
AED 1,914 total
includes taxes & fees
24 Sep - 25 Sep
Peaceful Stay Near Current River
Exterior

13. Nat's Cozy River Cabin Quiet 2-bedroom cabin with Current River views

Nat's Cozy River Cabin Quiet 2-bedroom cabin with Current River views
van buren
The price is AED 569
AED 1,130 total
includes taxes & fees
24 Sep - 25 Sep
Nat's Cozy River Cabin Quiet 2-bedroom cabin with Current River views
Exterior

14. Hogan's Hideout Cozy Cottage #5

Hogan's Hideout Cozy Cottage #5
Eminence
9.6 out of 10, Exceptional, (10 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 AED 533
AED 790 total
includes taxes & fees
24 Sep - 25 Sep
Hogan's Hideout Cozy Cottage #5
Exterior

15. 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 AED 547
AED 876 total
includes taxes & fees
24 Sep - 25 Sep
Easy Street Apartment
Property grounds

16. 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 traveler
The price is AED 533
AED 818 total
includes taxes & fees
24 Sep - 25 Sep
Hogan's Hideout Cottage #8
Property grounds

17. #ContemplationCabin on the Jacks Fork River!

#ContemplationCabin on the Jacks Fork River!
Summersville
10.0 out of 10, Exceptional, (87 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 AED 918
AED 1,311 total
includes taxes & fees
6 Oct - 7 Oct
#ContemplationCabin on the Jacks Fork River!
WiFi

18. Cozy Corner

Cozy Corner
Van Buren
9.8 out of 10, Exceptional, (10 reviews)
"Host was amazing and extremely responsive!! Close to everything we wanted to do"
United States
Dierdre
The price is AED 547
AED 876 total
includes taxes & fees
24 Sep - 25 Sep
Cozy Corner
Outdoor dining

19. 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, (24 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 AED 496
AED 922 total
includes taxes & fees
27 Sep - 28 Sep
Quiet 2 story Cabin on 32 acres near eleven point river
Coffee/tea maker, fridge, microwave, oven

20. 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 AED 441
AED 539 total
includes taxes & fees
24 Sep - 25 Sep
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock
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

“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.

10/10 Excellent
"This is a great place to stay. Roomy, well furnished, well equipped kitchen. Beautiful views, and super clean inside. Would recommend."
Daniel C. 2-night trip
Posted 3 days ago
“The Cabin”@ Serenity Ranch. Centrally located to all the wonders of Shannon co.

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?

Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!: Visitors give good reviews to this Winona vacation home rental, which 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 dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a 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 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.