Holiday Homes in Winona

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Find holiday rentals that suit your style

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Cabins
Cabins
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Cottages
Cottages

Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Winona holiday homes

A wooden interior with a bathroom featuring a sink, mirror, and towel rack. A door leads to a kitchen area with a 'GROCERY' sign.

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
9.6 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 NZ$323
includes taxes & fees
7 Nov - 8 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.

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)
"It was the perfect place to stay after a day on the river. Great host and property."
United States
Jeffery L.
The price is NZ$499
includes taxes & fees
8 Nov - 9 Nov
Bungalow with Hot Tub in Birch Tree
A kitchen with dark wooden cabinets, a white refrigerator, a coffee maker, and a window with a view of trees.

3. 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 NZ$501
includes taxes & fees
8 Nov - 9 Nov
Newly renovated early 1900’s farmhouse
A laundry area with two Samsung washing machines, a wicker basket with towels, and a small glass jar.

4. 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 NZ$385
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.

5. 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 NZ$860
includes taxes & fees
18 Nov - 19 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.

6. 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 NZ$350
includes taxes & fees
18 Nov - 19 Nov
Home Near Eleven Point River & Nat'l Forest!
A wooden deck with a railing, a chair, and a view of a forested area.

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, (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 NZ$1,020
includes taxes & fees
12 Nov - 13 Nov
Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12
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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Learn more about Winona

Nestled among the Ozarks, this small town serves as gateway to Rocky Falls where crystal waters cascade over ancient pink granite. Hikers and nature lovers can explore Mark Twain National Forest trails or float the pristine Current River for a perfect outdoor adventure.

See all hotels in Winona
A river surrounded by dense green forest.