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
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 AU$952
includes taxes & fees
23 Sept - 24 Sept
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.
The price is AU$291
includes taxes & fees
28 Sept - 29 Sept
“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 AU$188
includes taxes & fees
27 Sept - 28 Sept
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.
The price is AU$587
includes taxes & fees
23 Sept - 24 Sept
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 AU$441
includes taxes & fees
4 Oct - 5 Oct
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 AU$471
includes taxes & fees
23 Sept - 24 Sept
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 AU$421
includes taxes & fees
24 Sept - 25 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 AU$633
includes taxes & fees
7 Oct - 8 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.
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Top Winchester Hotel Reviews

French Quarter Inn

French Quarter Inn

10/10 Excellent
"Wonderful staff, excellent breakfast, great room"
Thomas 1-night trip
Posted 12 hours ago
French Quarter Inn

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
2,451
Accommodation
40 Holiday Homes
Lowest Price
AU$77
Highest Price
AU$424