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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Winchester holiday homes

Exterior

Mountain Views w/Hot Tub, 95” TV & Trail Access

Mountain Views w/Hot Tub, 95” TV & Trail Access
Shenandoah Farms
The price is £240
includes taxes & fees
15 Jul - 16 Jul
Mountain Views w/Hot Tub, 95” TV & Trail Access
Property grounds

Mountain Retreat with Hot Tub Near Shenandoah National Park, Virginia

Mountain Retreat with Hot Tub Near Shenandoah National Park, Virginia
Shenandoah Valley
The price is £349
includes taxes & fees
15 Jul - 16 Jul
Mountain Retreat with Hot Tub Near Shenandoah National Park, Virginia
Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (32 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is £169
includes taxes & fees
15 Jul - 16 Jul
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, (47 reviews)
"What an absolutely lovely and peaceful place to stay! We had a wonderful visit. "
United States
Stephanie T.
The price is £233
includes taxes & fees
19 Jul - 20 Jul
Newly renovated Farm cottage with Mountain views
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 £284
includes taxes & fees
3 Aug - 4 Aug
Bluemont home just minutes to wineries, breweries, hiking and more!
Fridge, microwave, oven, stovetop

Bend of Brothers’ | Riverfront Cottage Shenandoah

Bend of Brothers’ | Riverfront Cottage Shenandoah
Front Royal
The price is £305
includes taxes & fees
15 Jul - 16 Jul
Bend of Brothers’ | Riverfront Cottage Shenandoah
Coffee/tea maker, fridge, microwave, oven

Greek Spa • Private Acreage • Stonefire pizza oven

Greek Spa • Private Acreage • Stonefire pizza oven
Front Royal
6.0 out of 10, (2 reviews)
"Wonderful!"
United States
jmichaelcopas
The price is £238
includes taxes & fees
15 Jul - 16 Jul
Greek Spa • Private Acreage • Stonefire pizza oven
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 £234
includes taxes & fees
15 Jul - 16 Jul
Mountain home w/ hot tub & sunroom
Dining

Comfy Getaway in Strasburg, VA!

Comfy Getaway in Strasburg, VA!
Strasburg
The price is £258
includes taxes & fees
13 Aug - 14 Aug
Comfy Getaway in Strasburg, VA!
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, (9 reviews)
"Nice house in a good central location. "
United States
Mitchell V.
The price is £266
includes taxes & fees
2 Aug - 3 Aug
Cameron Charmer pristine downtown apt with double master suites
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, (12 reviews)
"Roomy, well stocked kitchen, and great view. Appreciated the chopsticks!"
United States
Brian T.
The price is £562
includes taxes & fees
15 Jul - 16 Jul
⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
Interior

4BR Golf Retreat | 3 Courses | Pool Table

4BR Golf Retreat | 3 Courses | Pool Table
Front Royal
10.0 out of 10, Exceptional, (1 review)
"Home was clean and looked like it had recently been remodeled/updated. The host was very responsive and when the oven wasn't working properly, they went to Lowes and purchased a new one immediately! Made our short trip much easier not having to eat out or find a last minute option for our kids/babysitter on Friday evening. We were only in town from Thursday-Sunday, and it was perfect for the 5 of us. The pool table was a fun addition for the kids. The only minor complaint I have is that I wish I...
United States
Crystal H.
The price is £425
includes taxes & fees
6 Aug - 7 Aug
4BR Golf Retreat | 3 Courses | Pool Table
Terrace/patio

The Royal Cabin | Private Getaway w/ Hot Tub, Game Room, Historic Log Cabin

The Royal Cabin | Private Getaway w/ Hot Tub, Game Room, Historic Log Cabin
Front Royal
9.8 out of 10, Exceptional, (14 reviews)
"House was very clean and well stocked. Great outdoor games for all ages. Perfect for our family and friends as we celebrated a wedding."
United States
mollie g.
The price is £1,291
includes taxes & fees
31 Jul - 1 Aug
The Royal Cabin | Private Getaway w/ Hot Tub, Game Room, Historic Log Cabin
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, (24 reviews)
"Host was super nice and location was pretty. "
United States
Kimberly B.
The price is £205
includes taxes & fees
19 Jul - 20 Jul
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
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
9.8 out of 10, Exceptional, (7 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 £310
includes taxes & fees
16 Jul - 17 Jul
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
9.0 out of 10, Wonderful, (26 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 £205
includes taxes & fees
19 Jul - 20 Jul
Modern, family-friendly, nature packed getaway
Outdoor dining

New Playground•Fenced Yard•Hot Tub•King Bed•Pets

New Playground•Fenced Yard•Hot Tub•King Bed•Pets
Harpers Ferry
10.0 out of 10, Exceptional, (29 reviews)
"Host was helpful and everything was wonderful."
United States
Karen
The price is £306
includes taxes & fees
15 Jul - 16 Jul
New Playground•Fenced Yard•Hot Tub•King Bed•Pets
Fridge, oven, stovetop, dishwasher

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
The price is £247
includes taxes & fees
27 Jul - 28 Jul
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Smart TV, fireplace, DVD player, books

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Harpers Ferry
9.6 out of 10, Exceptional, (109 reviews)
"Wonderful place to stay. Comfotable beds and big enough for a large crowd. The property owners are incredibly kind and responsive. Our family loved our stay. "
United States
Jenn C.
The price is £294
includes taxes & fees
19 Jul - 20 Jul
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
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

Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"The room was nice & clean. The staff was very helpful. I would definitely stay here again."
Donna 1-night trip
Posted 5 hours ago
Spark by Hilton Winchester

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
203
Accommodation
690 Holiday Homes
Lowest Price
£169
Highest Price
£1,291