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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sep - 13 Sep

Our top choices for Winchester vacation 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 AED 496
AED 805 total
includes taxes & fees
21 May - 22 May
Mountain View Bungalow in Front Royal
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 AED 727
AED 1,294 total
includes taxes & fees
21 May - 22 May
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 AED 647
AED 1,178 total
includes taxes & fees
1 Jun - 2 Jun
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 503
AED 1,329 total
includes taxes & fees
25 May - 26 May
Bluemont home just minutes to wineries, breweries, hiking and more!
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 AED 529
AED 1,114 total
includes taxes & fees
26 May - 27 May
Newly renovated Farm cottage with Mountain views
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, (11 reviews)
"Roomy, well stocked kitchen, and great view. Appreciated the chopsticks!"
United States
Brian T.
⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
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
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 AED 529
AED 1,360 total
includes taxes & fees
9 Jun - 10 Jun
Greek Spa on private acreage! Stonefire pizza oven
Dining

Comfy Getaway in Strasburg, VA!

Comfy Getaway in Strasburg, VA!
Strasburg
The price is AED 625
AED 1,488 total
includes taxes & fees
3 Jun - 4 Jun
Comfy Getaway in Strasburg, VA!
4 bedrooms, desk, iron/ironing board, travel crib

4BR Golf Retreat • 3 Courses • Pool Table

4BR Golf Retreat • 3 Courses • Pool Table
Front Royal
The price is AED 955
AED 1,886 total
includes taxes & fees
28 May - 29 May
4BR Golf Retreat • 3 Courses • Pool Table
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 AED 496
AED 1,174 total
includes taxes & fees
22 May - 23 May
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
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, (26 reviews)
"Host was helpful and everything was wonderful."
United States
Karen
The price is AED 961
AED 1,925 total
includes taxes & fees
22 May - 23 May
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Outdoor dining

Cozy Lakeside Homestead

Cozy Lakeside Homestead
Wardensville
10.0 out of 10, Exceptional, (213 reviews)
"Paula was very welcoming and told us everything we needed to know! We had a wonderful and relaxing weekend."
United States
Stephanie H.
The price is AED 826
AED 1,133 total
includes taxes & fees
2 Jun - 3 Jun
Cozy Lakeside Homestead
3 bedrooms, iron/ironing board, travel crib, WiFi

Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (34 reviews)
"Very nice home to enjoy a weekend away at! "
United States
Jessica W.
The price is AED 610
AED 1,574 total
includes taxes & fees
21 May - 22 May
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
TV, fireplace

Chalet in Harpers Ferry

Chalet in Harpers Ferry
Harpers Ferry
10.0 out of 10, Exceptional, (3 reviews)
"Great time. In the mountains. Clean. Ease of communication. Would stay again"
United States
Courtney C.
Chalet in Harpers Ferry
Terrace/patio

Modern luxury, walk to Washington St and downtown, EV, Movie room, Spa bathroom

Modern luxury, walk to Washington St and downtown, EV, Movie room, Spa bathroom
Bolivar
10.0 out of 10, Exceptional, (50 reviews)
"We appreciated the excellent communication with our host, spotless accommodations, bright lighting, well-appointed kitchen—and the provided coffee. "
United States
Cara B.
The price is AED 533
AED 1,265 total
includes taxes & fees
21 May - 22 May
Modern luxury, walk to Washington St and downtown, EV, Movie room, Spa bathroom
Exterior

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Harpers Ferry
10.0 out of 10, Exceptional, (160 reviews)
"Had a great stay at Jay's Spy House. Super location and nicely modernized house in the very heart of Harper's Ferry historic district. Jay was very attentive to anything we needed, which turned out to be very little, since everything was provided. Definitely recommend at stay here if visiting HF. "
United States
Bob S.
The price is AED 698
AED 1,473 total
includes taxes & fees
21 May - 22 May
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Interior

Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!

Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
Harpers Ferry
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful home. Very attentive hosts, great location. We enjoyed every minute at this home. "
United States
Katrina
The price is AED 832
AED 1,755 total
includes taxes & fees
11 Jun - 12 Jun
Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
3 bedrooms, travel crib, WiFi, bed sheets

Rustic Barn Retreat w Hot Tub, Game Room & FirePit

Rustic Barn Retreat w Hot Tub, Game Room & FirePit
Wardensville
Rustic Barn Retreat w Hot Tub, Game Room & FirePit
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 AED 555
AED 1,142 total
includes taxes & fees
2 Jun - 3 Jun
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
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

Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"Great."
Richard 4-night trip
Posted 4 hours ago
Quality Inn Winchester

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