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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sep - 6 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 809 total
includes taxes & fees
13 May - 14 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 AED 529
AED 1,114 total
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.
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 AED 808
AED 1,721 total
includes taxes & fees
13 May - 14 May
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 AED 312
AED 1,111 total
includes taxes & fees
13 May - 14 May
Greek Spa on private acreage! Stonefire pizza oven
Dining

Comfy Getaway in Strasburg, VA!

Comfy Getaway in Strasburg, VA!
Strasburg
The price is AED 436
AED 1,242 total
includes taxes & fees
13 May - 14 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 AED 801
AED 1,716 total
includes taxes & fees
13 May - 14 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 AED 951
AED 1,935 total
includes taxes & fees
13 May - 14 May
Luxury Riverfront Home Getaway with Hot Tub
Property grounds

Virginia Mirror Cabin

Virginia Mirror Cabin
Linden Virginia
The price is AED 1,194
AED 1,379 total
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 AED 327
AED 836 total
includes taxes & fees
13 May - 14 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 AED 430
AED 949 total
includes taxes & fees
13 May - 14 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 AED 559
AED 1,452 total
includes taxes & fees
25 May - 26 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 AED 538
AED 1,467 total
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 AED 459
AED 994 total
includes taxes & fees
18 May - 19 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 AED 566
AED 1,359 total
includes taxes & fees
1 Jun - 2 Jun
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 AED 516
AED 1,113 total
includes taxes & fees
31 May - 1 Jun
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 AED 658
AED 1,313 total
includes taxes & fees
13 May - 14 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 AED 493
AED 1,250 total
includes taxes & fees
13 May - 14 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 AED 661
AED 1,486 total
includes taxes & fees
13 May - 14 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

TRU By Hilton Winchester

TRU By Hilton Winchester

10/10 Excellent
"Property felt safe and convenient during travel. Well lit, clean exterior. Gentlemen at the front desk was professional, polite and quick with check in. Entrances to property were convenient to elevators etc. Very clean lobby and room. We did not partake in the breakfast but it looked clean and well stocked. Very nice stay. Definitely recommend."
Cassandra 1-night trip
Posted 2 hours ago
TRU By Hilton Winchester

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