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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Winchester vacation homes

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 AED 1,405
AED 1,773 total
includes taxes & fees
14 Jul - 15 Jul
Mountain Retreat with Hot Tub Near Shenandoah National Park, Virginia
Exterior

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

Mountain Views w/Hot Tub, 95” TV & Trail Access
Shenandoah Farms
The price is AED 690
AED 1,217 total
includes taxes & fees
14 Jul - 15 Jul
Mountain Views w/Hot Tub, 95” TV & Trail Access
Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (31 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is AED 496
AED 814 total
includes taxes & fees
12 Jul - 13 Jul
Mountain View Bungalow in Front Royal
Fridge, microwave, oven, stovetop

Bend of Brothers’ | Riverfront Cottage Shenandoah

Bend of Brothers’ | Riverfront Cottage Shenandoah
Front Royal
The price is AED 764
AED 1,485 total
includes taxes & fees
12 Jul - 13 Jul
Bend of Brothers’ | Riverfront Cottage Shenandoah
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 AED 529
AED 1,114 total
includes taxes & fees
20 Jul - 21 Jul
Newly renovated Farm cottage with Mountain views
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 AED 605
AED 1,128 total
includes taxes & fees
14 Jul - 15 Jul
Mountain home w/ hot tub & sunroom
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 AED 624
AED 1,449 total
includes taxes & fees
4 Aug - 5 Aug
Bluemont home just minutes to wineries, breweries, hiking and more!
Living area

Luxury Riverfront Home Getaway with Hot Tub

Luxury Riverfront Home Getaway with Hot Tub
Warren County
Luxury Riverfront Home Getaway with Hot Tub
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.
Cameron Charmer pristine downtown apt with double master suites
Smart TV, fireplace, video games, foosball

⭐️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 AED 1,349
AED 2,719 total
includes taxes & fees
12 Jul - 13 Jul
⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
Fridge, microwave, oven, stovetop

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 AED 389
AED 1,213 total
includes taxes & fees
13 Jul - 14 Jul
Greek Spa • Private Acreage • Stonefire pizza oven
Dining

Comfy Getaway in Strasburg, VA!

Comfy Getaway in Strasburg, VA!
Strasburg
The price is AED 624
AED 1,476 total
includes taxes & fees
9 Aug - 10 Aug
Comfy Getaway in Strasburg, VA!
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, (13 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 Royal Cabin | Private Getaway w/ Hot Tub, Game Room, Historic Log Cabin
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)
The price is AED 830
AED 2,119 total
includes taxes & fees
15 Jul - 16 Jul
4BR Golf Retreat | 3 Courses | Pool Table
Outdoor dining

Cozy Lakeside Homestead

Cozy Lakeside Homestead
Wardensville
10.0 out of 10, Exceptional, (218 reviews)
"Great place! We enjoyed the large family table, cute rooms, hot tub, and the mountain air! "
United States
Megan M.
The price is AED 826
AED 1,161 total
includes taxes & fees
22 Jul - 23 Jul
Cozy Lakeside Homestead
Terrace/patio

Harpers Ferry Luxury, Spa Bathroom, Movie Room, high-end design and furnishings

Harpers Ferry Luxury, Spa Bathroom, Movie Room, high-end design and furnishings
Bolivar
9.8 out of 10, Exceptional, (39 reviews)
"Great place to stay for the weekend."
United States
Bea G.
The price is AED 595
AED 1,366 total
includes taxes & fees
12 Jul - 13 Jul
Harpers Ferry Luxury, Spa Bathroom, Movie Room, high-end design and furnishings
TV, fireplace, stereo, offices

Modern Cabin w Hot Tub & Indoor Pool/Gym Access!

Modern Cabin w Hot Tub & Indoor Pool/Gym Access!
The Woods
8.8 out of 10, Excellent, (11 reviews)
The price is AED 805
AED 1,631 total
includes taxes & fees
13 Jul - 14 Jul
Modern Cabin w Hot Tub & Indoor Pool/Gym Access!
2 bedrooms, travel crib, WiFi, bed sheets

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
Harpers Ferry
10.0 out of 10, Exceptional, (17 reviews)
"Great spot"
China
Clara
The price is AED 661
AED 1,145 total
includes taxes & fees
12 Jul - 13 Jul
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
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 AED 380
AED 1,032 total
includes taxes & fees
13 Jul - 14 Jul
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Interior

Cozy Farmhouse by Shenandoah with Mountain Views

Cozy Farmhouse by Shenandoah with Mountain Views
2, East Luray
10.0 out of 10, Exceptional, (17 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.
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

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"This is a beautiful B&B. Perfect location & very helpful staff. I highly recommend it."
Bryan 1-night trip
Posted 6 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG

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