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

Holiday Homes in Winchester

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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 Winchester holiday homes

A living room with a fireplace, a sofa, a coffee table, and a dining area with chairs.

1. Quiet Farm Escape | Fishing, Nature & Views

Quiet Farm Escape | Fishing, Nature & Views
Winchester
The price is €619
includes taxes & fees
9 Nov - 10 Nov
Quiet Farm Escape | Fishing, Nature & Views
A small, single-story cabin with a porch, a front door, and a wreath decoration.

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 €188
includes taxes & fees
9 Nov - 10 Nov
“Serenity Now” cozy 2BR country cabin in the heart of Amish Country and hiking
A modern kitchen with a central island, bar stools, a hanging light fixture, and a fireplace.

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 €359
includes taxes & fees
9 Nov - 10 Nov
Grain Bin - Unique Stay
A modern kitchen with a dark wooden table, two bar stools, a built-in oven, and pendant lighting.

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 €153
includes taxes & fees
16 Nov - 17 Nov
1 Bed/1 Bath Guest House
An outdoor patio area with a stone fire pit, a hot tub, and outdoor seating.

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 €249
includes taxes & fees
10 Nov - 11 Nov
Sunset Cabin-Adults Only Hot Tub Getaway
A hot tub on a wooden deck with a view of a river and trees.

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 €322
includes taxes & fees
16 Nov - 17 Nov
Southern Ohio Retreat w/ Private Hot Tub
A living room with a wooden entertainment center, a zebra-patterned rug, and a dining area with a table and chairs.

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 €270
includes taxes & fees
18 Nov - 19 Nov
Experience Peace, Relaxation and Comfort in Kentucky with a touch of KENYA!
A living room with a sofa, a coffee table, and a lamp.

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 €370
includes taxes & fees
12 Nov - 13 Nov
Historic River Town Retreat w/ Screened Porch
A hot tub with water jets, surrounded by stone walls and outdoor seating.

9. The Cabin at 114 Main Street with Hot Tub

The Cabin at 114 Main Street with Hot Tub
Augusta
The price is €325
includes taxes & fees
8 Nov - 9 Nov
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.
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Top Winchester Hotel Reviews

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

10/10 Excellent
"The cabin was great. It was a little difficult to turn a 16ft box trailer in the driveway but I will stay again. I will just try to take a smaller trailer. Perfect cabin for a couple or a family. The owner is great at communicating and was very polite. Highly recommend!"
Sheila P. 8-night trip
Posted 11 hours ago
Rustic Cabin with modern amenities and 1 acre stocked Fishing Lake !

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
85
Accommodation
44 Holiday Homes
Lowest Price
€153
Highest Price
€619