Holiday Homes in Winchester

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 July - 12 July
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Winchester holiday homes

Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (25 reviews)
"Super cute, super clean and super comfortable!! Close and convenient to Shenandoah NP. Would definitely stay again!"
United States
Brian B.
The price is AU$305
includes taxes & fees
14 May - 15 May
Mountain View Bungalow in Front Royal
Property grounds

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (40 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is AU$423
includes taxes & fees
14 May - 15 May
Newly renovated Farm cottage with Mountain views
Exterior

Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.4 out of 10, Exceptional, (6 reviews)
"Nice house in a good central location. "
United States
Mitchell V.
The price is AU$479
includes taxes & fees
20 May - 21 May
Cameron Charmer pristine downtown apt with double master suites
Interior

Bluemont home just minutes to wineries, breweries, hiking and more!

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
The price is AU$515
includes taxes & fees
2 June - 3 June
Bluemont home just minutes to wineries, breweries, hiking and more!
Fridge, microwave, oven, stovetop

Greek Spa on private acreage! Stonefire pizza oven

Greek Spa on private acreage! Stonefire pizza oven
Front Royal
The price is AU$467
includes taxes & fees
14 May - 15 May
Greek Spa on private acreage! Stonefire pizza oven
Dining

Comfy Getaway in Strasburg, VA!

Comfy Getaway in Strasburg, VA!
Strasburg
The price is AU$459
includes taxes & fees
14 May - 15 May
Comfy Getaway in Strasburg, VA!
Property grounds

4BR Golf Retreat • 3 Courses • Pool Table

4BR Golf Retreat • 3 Courses • Pool Table
Front Royal
The price is AU$682
includes taxes & fees
19 May - 20 May
4BR Golf Retreat • 3 Courses • Pool Table
Exterior

Luxury Riverfront Home Getaway with Hot Tub

Luxury Riverfront Home Getaway with Hot Tub
Warren County
The price is AU$731
includes taxes & fees
18 May - 19 May
Luxury Riverfront Home Getaway with Hot Tub
Property grounds

Virginia Mirror Cabin

Virginia Mirror Cabin
Linden Virginia
The price is AU$505
includes taxes & fees
19 May - 20 May
Virginia Mirror Cabin
Exterior detail

Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper

Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
Rixeyville
9.6 out of 10, Exceptional, (8 reviews)
"Host and everything was very accommodating! Very nice stay"
United States
James G.
The price is AU$313
includes taxes & fees
14 May - 15 May
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
Fridge, microwave, oven, stovetop

Historical home, walkable to many restaurants and shops.

Historical home, walkable to many restaurants and shops.
Luray
9.8 out of 10, Exceptional, (86 reviews)
"Very cute house with lots of charm. Beds were comfortable. Host responded to messages quickly. "
United States
Nicole G.
The price is AU$362
includes taxes & fees
18 May - 19 May
Historical home, walkable to many restaurants and shops.
Smart TV, fireplace

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Harpers Ferry
10.0 out of 10, Exceptional, (7 reviews)
"Welcoming host, great place!"
United States
Amanda M.
The price is AU$553
includes taxes & fees
18 May - 19 May
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Outdoor dining

Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Harpers Ferry
10.0 out of 10, Exceptional, (25 reviews)
"Host was helpful and everything was wonderful."
United States
Karen
The price is AU$545
includes taxes & fees
14 May - 15 May
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Dining

Modern, family-friendly, nature packed getaway

Modern, family-friendly, nature packed getaway
Berkeley Springs
8.8 out of 10, Excellent, (25 reviews)
"House was very clean and well stocked! Very comfortable and within short distance of a lovely town Berkley Springs."
United States
Annie W.
The price is AU$376
includes taxes & fees
14 May - 15 May
Modern, family-friendly, nature packed getaway
Interior

Stone Cabin on Valley View: Fire Pit + Hot Tub

Stone Cabin on Valley View: Fire Pit + Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful scenery! Beautiful home! Wonderful hosts!"
United States
Brian S.
The price is AU$492
includes taxes & fees
17 May - 18 May
Stone Cabin on Valley View: Fire Pit + Hot Tub
Property grounds

Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location

Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
Harpers Ferry
7.6 out of 10, Good, (27 reviews)
"The inside was well done and clean. Even though the neighbors are close, they were quiet. My husband and I were able to relax in a comfortable setting."
United States
Melissa H.
The price is AU$402
includes taxes & fees
1 June - 2 June
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
Fridge, microwave, oven, stovetop

Spring Getaway with Trails & Nature

Spring Getaway with Trails & Nature
Star Tannery
10.0 out of 10, Exceptional, (7 reviews)
"Zepp Trails is a great house and a great location with comfortable beds and wonderful trails. that go through the woods and fields. "
United States
Josh T.
The price is AU$515
includes taxes & fees
14 May - 15 May
Spring Getaway with Trails & Nature
Exterior

Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly

Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly
Luray
9.8 out of 10, Exceptional, (45 reviews)
"Amazing stay in Luray, VA. House was very clean and up kept "
United States
Shedrick J.
The price is AU$466
includes taxes & fees
17 May - 18 May
Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly
Interior

Cozy Farmhouse by Shenandoah with Mountain Views

Cozy Farmhouse by Shenandoah with Mountain Views
2, East Luray
10.0 out of 10, Exceptional, (14 reviews)
"Thank you so much for a great stay. It is an outstanding house in a great location. Close to all local restaurants and activities."
United States
Scott H.
The price is AU$547
includes taxes & fees
14 May - 15 May
Cozy Farmhouse by Shenandoah with Mountain Views
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

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"The staff was helpful and kind. The architecture was incredible."
Allison 1-night trip
Posted 3 hours ago
The George Washington Hotel, A Wyndham Grand Hotel

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
275
Accommodation
665 Holiday Homes
Lowest Price
AU$305
Highest Price
AU$731