Photo by Jessica Richter

Search Vacation Homes in Winona

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Vacation Homes in Winona

Unique cabins in the woods<br>Not friendly for Street Bikes.
Fridge, microwave, oven, stovetop

Unique cabins in the woods<br>Not friendly for Street Bikes.

10.0 out of 10, Exceptional, (103)
"We loved our stay at this property. As other reviews have mentioned the cabin is very well appointed with everything we needed. The beds were very comfortable and the shower was great, two very important things after a long day at the river!"
Unique cabins in the woods<br>Not friendly for Street Bikes.
4-bedroom RIVER FRONT home located on the beautiful Current River in Van Buren
Property grounds

4-bedroom RIVER FRONT home located on the beautiful Current River in Van Buren

10.0 out of 10, Exceptional, (2)
"The propertyb was great spacious and very accomodating "
4-bedroom RIVER FRONT home located on the beautiful Current River in Van Buren
RIVER FRONT HOUSE
Property grounds

RIVER FRONT HOUSE

9.6 out of 10, Exceptional, (39)
"House was in a great location for a family stay."
RIVER FRONT HOUSE
The Loft on the River with Private Gravel bar!!
Property grounds

The Loft on the River with Private Gravel bar!!

8.4 out of 10, Very Good, (17)
"We had a great time and other than there was no broom so hard to sweep the sand from the beach, but that was very minor. Overall it was clean and we all enjoyed it! Will come back again next year!"
The Loft on the River with Private Gravel bar!!
Unbeatable convenience in amazing Eminence!
Dining

Unbeatable convenience in amazing Eminence!

10.0 out of 10, Exceptional, (14)
Unbeatable convenience in amazing Eminence!
Whole house, secluded getaway near Alley Springs, Eminence , Missouri.
Exterior

Whole house, secluded getaway near Alley Springs, Eminence , Missouri.

10.0 out of 10, Exceptional, (3)
"This location was a perfect place for a large family gathering. There was adequate space for a couple of families to stay overnight! Close to Harvey’s canoe/raft rentals! The host was very helpful!"
Whole house, secluded getaway near Alley Springs, Eminence , Missouri.
Private scenic Ozark Mountain retreat near beautiful Current River; sleeps 1-10!
Terrace/patio

Private scenic Ozark Mountain retreat near beautiful Current River; sleeps 1-10!

10.0 out of 10, Exceptional, (20)
"Cute house, great accommodations, great location!"
Private scenic Ozark Mountain retreat near beautiful Current River; sleeps 1-10!
Triple H Properties
Property grounds

Triple H Properties

8.6 out of 10, Excellent, (27)
"Lori’s place was a nice spot for a two night stay"
Triple H Properties
Guests enjoy their own one bedroom apartment in the Ozarks
Property grounds

Guests enjoy their own one bedroom apartment in the Ozarks

10.0 out of 10, Exceptional, (68)
"Second time staying there! Great location!"
Guests enjoy their own one bedroom apartment in the Ozarks
The Cabin on Current River with Private Gravel Bar!!
Outdoor dining

The Cabin on Current River with Private Gravel Bar!!

8.6 out of 10, Excellent, (25)
"Due to a situation beyond the property owners control we weren’t able to stay at the original cabin but they acted quickly and moved us to another. Great service and we had a great time. "
The Cabin on Current River with Private Gravel Bar!!
Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12
Terrace/patio

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

2.0 star property
10.0 out of 10, Exceptional, (6)
"Loved this property. New home near town and hiking trails of the Ozark National Scenic Wayerways. Conveniences near by. Homes is in excellent condition and recently constructed with all new interior furnishings. Owner is excellent to work with. Responded to needs and questions immediately. "
$543 nightly
The price is $567
Aug 11 - Aug 12
Total includes taxes and fees
Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12
5-bedroom house just outside of Big Spring-Ozark National Scenic Riverways!
Living area

5-bedroom house just outside of Big Spring-Ozark National Scenic Riverways!

6.0 out of 10, (2)
"Paige was great! Very prompt with a fridge issue we had. Great hospitality! Left us snacks!!"
5-bedroom house just outside of Big Spring-Ozark National Scenic Riverways!
Barn by The Creek- Barn turned bnb on a creek in Eminence, sleeps 10
Property grounds

Barn by The Creek- Barn turned bnb on a creek in Eminence, sleeps 10

10.0 out of 10, Exceptional, (3)
"It was a very good place to stay.It had everything we needed.None of the kids complained and it was comfortable."
Barn by The Creek- Barn turned bnb on a creek in Eminence, sleeps 10
Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride
Outdoor dining

Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride

9.4 out of 10, Exceptional, (13)
"Decent place, lots of ladybugs in the house!"
$240 nightly
The price is $240
Aug 25 - Aug 26
Total includes taxes and fees
Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride
The Jacks Fork Town House in Eminence
2 bedrooms, free WiFi, bed sheets

The Jacks Fork Town House in Eminence

9.6 out of 10, Exceptional, (16)
"Easy to find. We will stay again next year"
The Jacks Fork Town House in Eminence
Serene and cozy Ozark home - 3 mins to Alley Spring and the Jack's Fork river!
3 bedrooms, free WiFi, bed sheets

Serene and cozy Ozark home - 3 mins to Alley Spring and the Jack's Fork river!

2.0 star property
10.0 out of 10, Exceptional, (2)
"Lovely quiet cottage. Would love to stay again"
Serene and cozy Ozark home - 3 mins to Alley Spring and the Jack's Fork river!
Quaint Haven
Dining

Quaint Haven

9.6 out of 10, Exceptional, (8)
"Its close to food, stores and the river."
Quaint Haven
Sunshine Shack at Clearwater Lake (sleeps 6)
Property grounds

Sunshine Shack at Clearwater Lake (sleeps 6)

8.8 out of 10, Excellent, (10)
"Loved staying a week at Sunshine Shack. The screened in deck is perfect to watch the deer at dusk."
Sunshine Shack at Clearwater Lake (sleeps 6)
2-bedroom vacation home near Mark Twain National Forest
Interior

2-bedroom vacation home near Mark Twain National Forest

2.0 star property
10.0 out of 10, Exceptional, (8)
"We all really enjoyed our stay. "
2-bedroom vacation home near Mark Twain National Forest
The Big Beautiful Build
Spa

The Big Beautiful Build

The Big Beautiful Build
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.
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

Cute and comfy bedroom with 1 queen bed/private bath

Cute and comfy bedroom with 1 queen bed/private bath

10/10 Excellent
"Absolutely perfect!"
William R. 2-night trip
Posted 2 days ago
Cute and comfy bedroom with 1 queen bed/private bath