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

Holiday Homes in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winchester holiday homes

A two-story house with a front porch, a garage with two doors, and a small front yard with a flower decoration.

1. Quiet Farm Escape | Fishing, Nature & Views

Quiet Farm Escape | Fishing, Nature & Views
Winchester
The price is €901
includes taxes & fees
23 Oct - 24 Oct
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 retreat in the heart of Amish Country and hiking

“Serenity Now” cozy 2BR country retreat 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.
“Serenity Now” cozy 2BR country retreat in the heart of Amish Country and hiking
A modern kitchen with a dark wooden table, two bar stools, a built-in oven, and pendant lighting.

3. 1 Bed/1 Bath Guest House

1 Bed/1 Bath Guest House
Hillsboro
9.8 out of 10, Exceptional, (10 reviews)
"New and comfortable and private."
United States
Leigh K.
The price is €119
includes taxes & fees
6 Oct - 7 Oct
1 Bed/1 Bath Guest House
A modern kitchen with a central island, bar stools, a hanging light fixture, and a fireplace.

4. Grain Bin - Unique Stay

Grain Bin - Unique Stay
Peebles
9.2 out of 10, Wonderful, (25 reviews)
"Very nice stay. "
United States
Jennifer J.
Grain Bin - Unique Stay
A dark green wooden building with a black door, a window, and a small balcony with a 'hello' mat.

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 €260
includes taxes & fees
28 Sept - 29 Sept
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
6 Oct - 7 Oct
Southern Ohio Retreat w/ Private Hot Tub
A hot tub with water jets, surrounded by stone walls and outdoor seating.

7. The Cabin at 114 Main Street with Hot Tub

The Cabin at 114 Main Street with Hot Tub
Augusta
The price is €264
includes taxes & fees
23 Sept - 24 Sept
The Cabin at 114 Main Street with Hot Tub
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, (11 reviews)
"Really enjoyed our stay here! Very relaxing!!"
United States
Beth B.
The price is €382
includes taxes & fees
5 Oct - 6 Oct
Historic River Town Retreat w/ Screened Porch
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

French Quarter Inn

French Quarter Inn

10/10 Excellent
"Wonderful staff, excellent breakfast, great room"
Thomas 1-night trip
Posted 11 hours ago
French Quarter Inn

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
40
Accommodation
38 Holiday Homes
Lowest Price
€119
Highest Price
€901