Photo by Jessica Richter
Search Vacation Homes in Winona
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 33 Vacation Homes in Winona with updated reviews, rates, and availability.

Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!
Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!
10.0 out of 10, Exceptional, (60)

Whole house, secluded getaway near Alley Springs, Eminence , Missouri.
Whole house, secluded getaway near Alley Springs, Eminence , Missouri.
10.0 out of 10, Exceptional, (2)

Unbeatable convenience in amazing Eminence!
Unbeatable convenience in amazing Eminence!

2 Bedroom Home less than 2 miles to Jacks Fork River
2 Bedroom Home less than 2 miles to Jacks Fork River
10.0 out of 10, Exceptional, (20)

The Cabin on Current River with Private Gravel Bar!!
The Cabin on Current River with Private Gravel Bar!!
8.6 out of 10, Excellent, (25)

Unique cabins in the woods<br>Not friendly for Street Bikes. Beautifulin FALL!
Unique cabins in the woods<br>Not friendly for Street Bikes. Beautifulin FALL!
10.0 out of 10, Exceptional, (95)

Triple H Properties
Triple H Properties
8.8 out of 10, Excellent, (23)

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
10.0 out of 10, Exceptional, (2)
The price is SAR 938
SAR 1,832 total
includes taxes & fees
24 Apr - 25 Apr
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
Other property types in Winona

Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!
Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!
10.0 out of 10, Exceptional, (60)

Unique cabins in the woods<br>Not friendly for Street Bikes. Beautifulin FALL!
Unique cabins in the woods<br>Not friendly for Street Bikes. Beautifulin FALL!
10.0 out of 10, Exceptional, (95)

Secluded Ozarks Tiny House cabin in Eminence, MO
Secluded Ozarks Tiny House cabin in Eminence, MO
9.6 out of 10, Exceptional, (93)
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.
Recent reviews of Winona hotels
Recent reviews of Winona hotels

Secluded Ozarks Bunk House Cabin at Old Desperado Ranch
5/5 Excellent
Personal retreat
"Despite the constant, drenching rain, I enjoyed my quiet solitude retreat. The picture made me think it was more isolated than it is (there are other cabins and the trail-riding stables right across the road), but given the weather and time of year, I pretty much had the place to myself. The cabin itself is tiny, but very clean and well supplied. The hosts are very friendly and responsive and I would highly recommend if you’re in the area. The dirt road in May be a little intimidating for a small car, but was no problem for my Outback, despite the rainy conditions and minor rain runoff damage. "
A verified traveler stayed at Secluded Ozarks Bunk House Cabin at Old Desperado Ranch
Posted 10 days ago