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
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Winona vacation rentals

A living room with a black sofa, a patterned throw pillow, a flat-screen TV displaying 'Clemson,' a wooden wall, and a patterned rug.

1. 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)
"This property was exactly what we needed during a difficult time, and the hosts were wonderful and communicative. They installed a/cs in the bedrooms, and even surprised us with some goodies from their garden! The place was spotless, cool and updated and the bed and sofa are comfortable. I hope it's not booked when I return, because I will be!"
United States
Jennifer H.
The price is AED 441
AED 588 total
includes taxes & fees
14 Nov - 15 Nov
CountryComfortRetreat!!! 2-bedroom mobile home with AC in Birch Tree
A kitchen with wooden cabinets, a dining table, a chandelier, and a sign labeled "GROCERY".

2. 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, (30 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 463
AED 700 total
includes taxes & fees
9 Nov - 10 Nov
Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride
A hot tub with a wooden deck and a view of trees and a house in the background.

3. Bungalow with Hot Tub in Birch Tree

Bungalow with Hot Tub in Birch Tree
Birch Tree
10.0 out of 10, Exceptional, (6 reviews)
"It was the perfect place to stay after a day on the river. Great host and property."
United States
Jeffery L.
The price is AED 657
AED 1,043 total
includes taxes & fees
9 Nov - 10 Nov
Bungalow with Hot Tub in Birch Tree
A cabin with a wooden deck, two doors, and a small porch area.

4. 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
Hogan's Hideout Cottage #7
A kitchen with dark wooden cabinets, a white refrigerator, a coffee maker, and a window with a view of trees.

5. Newly renovated early 1900’s farmhouse

Newly renovated early 1900’s farmhouse
Birch Tree
10.0 out of 10, Exceptional, (32 reviews)
"It was perfect and we enjoyed the hospitality and community."
United States
Colleen
The price is AED 625
AED 1,047 total
includes taxes & fees
9 Nov - 10 Nov
Newly renovated early 1900’s farmhouse
A cabin with a wooden deck, a covered porch, and a gravel driveway.

6. Hogan's Hideout Cozy Cottage #5

Hogan's Hideout Cozy Cottage #5
Eminence
9.6 out of 10, Exceptional, (10 reviews)
"All we needed was a place to shower and a comfortable place to sleep after playing/floating the river all day. This place was perfect!"
United States
Mandy M.
Hogan's Hideout Cozy Cottage #5
A wooden deck with a metal railing overlooking a lake, surrounded by trees.

7. 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, (16 reviews)
"Perfect for a river trip"
United States
Jeremy H.
The price is AED 918
AED 1,211 total
includes taxes & fees
9 Nov - 10 Nov
New cabin located on the jacks fork river front.
A cabin with a wooden exterior, two windows, a door, and a porch with railings.

8. 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
Hogan's Hideout Cottage #8
A wooden cabin with a porch, surrounded by trees and grass.

9. 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 1,027 total
includes taxes & fees
9 Nov - 10 Nov
Nat's Cozy River Cabin Quiet 2-bedroom cabin with Current River views
A bedroom with a bed, a nightstand, a dresser, a window with curtains, and a ceiling fan.

10. Peaceful Farm Stay in Alton w/ Private Patio

Peaceful Farm Stay in Alton w/ Private Patio
3.0 star property
Alton
The price is AED 261
AED 542 total
includes taxes & fees
9 Nov - 10 Nov
Peaceful Farm Stay in Alton w/ Private Patio
A rustic cabin with a wooden exterior, a porch, and a picnic table.

11. 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 364
AED 586 total
includes taxes & fees
28 Nov - 29 Nov
Cozy quiet country getaway just minutes from the Current River
A cabin with a deck, a staircase, and a fire pit.

12. Easy Street Apartment

Easy Street Apartment
Van Buren
10.0 out of 10, Exceptional, (4 reviews)
"Great place. Would definitely go again."
United States
Jeramy T.
The price is AED 523
AED 777 total
includes taxes & fees
9 Nov - 10 Nov
Easy Street Apartment
Room

13. Cozy Corner

Cozy Corner
Van Buren
9.8 out of 10, Exceptional, (10 reviews)
"Great property! Very clean and close to town."
United States
Mindy R.
The price is AED 547
AED 802 total
includes taxes & fees
9 Nov - 10 Nov
Cozy Corner
A laundry area with two Samsung washing machines, a wicker basket with towels, and a small glass jar.

14. 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
9.2 out of 10, Wonderful, (12 reviews)
"Perfect spot to get away with the family!"
United States
Jennifer P.
The price is AED 532
AED 790 total
includes taxes & fees
9 Nov - 10 Nov
Family-Friendly 3BR/2BA Van Buren Home w/ Fire Pit & Starlink WiFi!
A single-story house with a gravel driveway leading to a wooden deck.

15. 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 1,794 total
includes taxes & fees
9 Nov - 10 Nov
3-bedroom/2 bath house in Van Buren MO located on the Current River
A kitchen with granite countertops, wooden cabinets, a stainless steel sink, and a wooden chair.

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

Home Near Eleven Point River & Nat'l Forest!
Alton
8.6 out of 10, Excellent, (4 reviews)
"Very convenient and quite."
United States
Stephen G.
The price is AED 290
AED 734 total
includes taxes & fees
9 Nov - 10 Nov
Home Near Eleven Point River & Nat'l Forest!
A rural property with a large yellow house, a fenced yard, and various animals including ducks and a cat.

17. Peaceful Farm Stay in Alton w/ Private Patio

Peaceful Farm Stay in Alton w/ Private Patio
Alton
The price is AED 275
AED 669 total
includes taxes & fees
9 Dec - 10 Dec
Peaceful Farm Stay in Alton w/ Private Patio
A wooden deck with a railing, a chair, and a view of a forested area.

18. 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 1,210
AED 2,029 total
includes taxes & fees
9 Nov - 10 Nov
Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12
A wooden bench with a white pillow featuring a bird, overlooking a calm lake with daffodils and a wooden structure in the background.

19. #ContemplationCabin on the Jacks Fork River!

#ContemplationCabin on the Jacks Fork River!
Summersville
10.0 out of 10, Exceptional, (89 reviews)
"The location is amazing! Private and secluded Jacks Fork experience! Would definitely love to return!"
United States
Mike S.
The price is AED 918
AED 1,263 total
includes taxes & fees
12 Nov - 13 Nov
#ContemplationCabin on the Jacks Fork River!
A kitchen with granite countertops, wooden cabinets, a stainless steel sink, and a wooden chair.

20. 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
9 Nov - 10 Nov
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.
View all properties

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Top Winona Hotel Reviews

A large, multi-story building with a prominent central tower, multiple balconies, and a landscaped front yard with trees and shrubs.
Echo Bluff State Park

Echo Bluff State Park

Echo Bluff State Park
Eminence

10/10 Excellent

This was comparable to any top luxury hotel in a large city. The duplex we stayed in was beautiful and very large.
United States
Mary
Reviewed July 30, 2022
Echo Bluff State Park

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.