Search Holiday Homes in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Winchester holiday homes

Property grounds

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (43 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is £229
includes taxes & fees
31 May - 1 Jun
Newly renovated Farm cottage with Mountain views
Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (25 reviews)
"We had a wonderful time and the amenities were perfect!"
United States
Douglas S.
The price is £166
includes taxes & fees
11 Jun - 12 Jun
Mountain View Bungalow in Front Royal
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 £345
includes taxes & fees
1 Jun - 2 Jun
Bluemont home just minutes to wineries, breweries, hiking and more!
Fridge, microwave, oven, stovetop

Greek Spa • Private Acreage • Stonefire pizza oven

Greek Spa • Private Acreage • Stonefire pizza oven
Front Royal
The price is £249
includes taxes & fees
1 Jun - 2 Jun
Greek Spa • Private Acreage • Stonefire pizza oven
Exterior

Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.6 out of 10, Exceptional, (7 reviews)
"Nice house in a good central location. "
United States
Mitchell V.
The price is £262
includes taxes & fees
1 Jun - 2 Jun
Cameron Charmer pristine downtown apt with double master suites
TV, offices

Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom
Front Royal
9.0 out of 10, Wonderful, (31 reviews)
"The house itself was clean, the beds are comfortable, and it is in a nice, quiet, and private location. The property manager was very pleasant and responsed to any questions or concerns quickly. "
United States
Elissa S.
The price is £240
includes taxes & fees
1 Jun - 2 Jun
Mountain home w/ hot tub & sunroom
Dining

Comfy Getaway in Strasburg, VA!

Comfy Getaway in Strasburg, VA!
Strasburg
The price is £260
includes taxes & fees
9 Jun - 10 Jun
Comfy Getaway in Strasburg, VA!
Interior

4BR Golf Retreat • 3 Courses • Pool Table

4BR Golf Retreat • 3 Courses • Pool Table
Front Royal
The price is £444
includes taxes & fees
9 Jun - 10 Jun
4BR Golf Retreat • 3 Courses • Pool Table
Living area

Luxury Riverfront Home Getaway with Hot Tub

Luxury Riverfront Home Getaway with Hot Tub
Warren County
The price is £402
includes taxes & fees
15 Jun - 16 Jun
Luxury Riverfront Home Getaway with Hot Tub
Smart TV, fireplace, video games, table football

⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!

⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
Front Royal
10.0 out of 10, Exceptional, (11 reviews)
"Roomy, well stocked kitchen, and great view. Appreciated the chopsticks!"
United States
Brian T.
The price is £555
includes taxes & fees
3 Jun - 4 Jun
⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
Property grounds

Virginia Mirror Cabin

Virginia Mirror Cabin
Linden Virginia
Virginia Mirror Cabin
Dining

Completely private suite with tub,kitchen, living room, & private entrance

Completely private suite with tub,kitchen, living room, & private entrance
Washington
10.0 out of 10, Exceptional, (20 reviews)
"Short walk to Inn at Little Washington and Pattyo's which we didn't realize and a reasonable way to drive Skyline Drive and visit in Ruckersville. Host was very helpful. "
United States
David
The price is £200
includes taxes & fees
1 Jun - 2 Jun
Completely private suite with tub,kitchen, living room, & private entrance
Exterior

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Martinsburg
9.8 out of 10, Exceptional, (23 reviews)
"Host was super nice and location was pretty. "
United States
Kimberly B.
The price is £191
includes taxes & fees
3 Jun - 4 Jun
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
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
9.8 out of 10, Exceptional, (11 reviews)
"Great tiny home by the owner’s house. Beautiful area (but not super convenient to shopping or restaurants). I thought it was great."
United States
John Mark
Charming tiny home only 15 mins from Town of Warrenton & Town of Culpeper
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, (50 reviews)
"Amazing stay in Luray, VA. House was very clean and up kept "
United States
Shedrick J.
The price is £249
includes taxes & fees
31 May - 1 Jun
Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly
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 £290
includes taxes & fees
1 Jun - 2 Jun
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Terrace/patio

Huckleberry Hills | Hot Tub & Fire Pit & Dogs

Huckleberry Hills | Hot Tub & Fire Pit & Dogs
Harpers Ferry
9.8 out of 10, Exceptional, (11 reviews)
"We had a great stay "
United States
Lauren O.
The price is £301
includes taxes & fees
15 Jun - 16 Jun
Huckleberry Hills | Hot Tub & Fire Pit & Dogs
Property grounds

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
Harpers Ferry
9.6 out of 10, Exceptional, (4 reviews)
"House was beautiful and fully equipped for our stay. The host was very communicative and we really enjoyed our time here. If in the area again would definitely stay here. "
United States
Maeve K.
The price is £297
includes taxes & fees
3 Jun - 4 Jun
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
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 £202
includes taxes & fees
30 May - 31 May
Modern, family-friendly, nature packed getaway
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, (89 reviews)
"We really enjoyed our stay! Great and clean space! "
United States
Emily S.
The price is £194
includes taxes & fees
31 May - 1 Jun
Historical home, walkable to many restaurants and shops.
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

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

6/10 Okay
"There is no restaurant. The lack of mirrors was irritating. There were hand mirrors in some rooms and not in others and they said they ran out. No fans in the bathrooms. Beds were nice."
Caroline 2-night trip
Posted less than an hour ago
Courtyard by Marriott Winchester

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
212
Accommodation
664 Holiday Homes
Lowest Price
£166
Highest Price
£555