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Our top choices for Winchester vacation homes

1. Quiet Farm Escape | Fishing, Nature & Views

Quiet Farm Escape | Fishing, Nature & Views
Winchester
The price is ¥73,337
¥109,834 total
includes taxes & fees
Dec 3 - Dec 4
Quiet Farm Escape | Fishing, Nature & Views

2. “Serenity Now” cozy 2BR country cabin in the heart of Amish Country and hiking

“Serenity Now” cozy 2BR country cabin in the heart of Amish Country and hiking
West Union
10.0 out of 10, Exceptional, (2 reviews)
"Clean, peaceful and relaxing!"
United States
April V.
The price is ¥21,536
¥34,505 total
includes taxes & fees
Nov 10 - Nov 11
“Serenity Now” cozy 2BR country cabin in the heart of Amish Country and hiking

3. Grain Bin - Unique Stay

Grain Bin - Unique Stay
Peebles
9.2 out of 10, Wonderful, (26 reviews)
"Very nice stay. "
United States
Jennifer J.
The price is ¥43,019
¥63,782 total
includes taxes & fees
Nov 12 - Nov 13
Grain Bin - Unique Stay

4. 1 Bed/1 Bath Guest House

1 Bed/1 Bath Guest House
Hillsboro
10.0 out of 10, Exceptional, (13 reviews)
"Very clean and neat! Very comfortable place to stay. We enjoyed out visit and would definitely book this property again."
United States
Brenda
The price is ¥18,899
¥26,774 total
includes taxes & fees
Nov 18 - Nov 19
1 Bed/1 Bath Guest House

5. Sunset Cabin-Adults Only Hot Tub Getaway

Sunset Cabin-Adults Only Hot Tub Getaway
Hillsboro
9.8 out of 10, Exceptional, (7 reviews)
"Great weekend thank you"
United States
Kris S.
The price is ¥28,503
¥43,863 total
includes taxes & fees
Nov 10 - Nov 11
Sunset Cabin-Adults Only Hot Tub Getaway

6. Southern Ohio Retreat w/ Private Hot Tub

Southern Ohio Retreat w/ Private Hot Tub
Georgetown
9.2 out of 10, Wonderful, (10 reviews)
"I truly enjoyed how clean and stocked the cabin was they had everything you could possibly need and some me and my family fully enjoyed the stay "
United States
Austin C.
The price is ¥44,960
¥57,244 total
includes taxes & fees
Dec 3 - Dec 4
Southern Ohio Retreat w/ Private Hot Tub

7. Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!

Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!
Dover
9.8 out of 10, Exceptional, (15 reviews)
"Great place and lots of space. "
United States
Amy M.
The price is ¥37,278
¥47,498 total
includes taxes & fees
Nov 10 - Nov 11
Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!

8. Historic River Town Retreat w/ Screened Porch

Historic River Town Retreat w/ Screened Porch
Ripley
9.4 out of 10, Exceptional, (12 reviews)
"Really enjoyed our stay here! Very relaxing!!"
United States
Beth B.
The price is ¥39,684
¥65,337 total
includes taxes & fees
Nov 12 - Nov 13
Historic River Town Retreat w/ Screened Porch

9. The Cabin at 114 Main Street with Hot Tub

The Cabin at 114 Main Street with Hot Tub
Augusta
The price is ¥28,458
¥57,220 total
includes taxes & fees
Nov 10 - Nov 11
The Cabin at 114 Main Street with Hot Tub
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.

Learn more about Winchester

Check out Adams Lake State Park and Serpent Mound—just a couple of the sights around Winchester.

A historic downtown area with a prominent clock tower and a green-roofed building.

Top reviews in Winchester