We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Winchester, VA and nearby

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 22 Rentals in the Winchester Area
loading...
From
$195
Per Night
1 / 12
Payment Protection
Winchester
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Details Reviews (2) Make Inquiry Similar Properties
From
$125
Per Night
1 / 11
Payment Protection
Winchester
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Details Make Inquiry Similar Properties

The following rentals are within 25 miles of Winchester, Virginia.

From
$210
Per Night
1 / 13
Payment Protection
Harpers Ferry, WV
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (3) Make Inquiry Similar Properties
From
$275
Per Night
1 / 38
Payment Protection
Harpers Ferry, WV
4 Bedrooms, 2 Bathrooms, Sleeps 14
Bookings
Details Reviews (6) Make Inquiry Similar Properties
5 of 5 stars Reviewed May 28, 2014
We traveled to Harpers Ferry with our adult children for an extended weekend of hiking, water sports and adventure. The house was absolutely perfect. It is very close to River...
4 of 5 stars Reviewed September 13, 2013
We stayed as a party of ten extended family members for a week at the end of August, and over all it was an excellent experience. The booking process was very simple, on line...
See all reviews
From
$140
Per Night
1 / 44
Payment Protection
Front Royal
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (16) Make Inquiry Similar Properties
5 of 5 stars Reviewed November 14, 2014
We stayed in November 2014 and had a great stay. The property was as advertised and the hot tub was awesome after hiking! Saw a shooting star from the hot tub - would be really...
4 of 5 stars Reviewed September 29, 2014
Very well-stocked and appointed cabin with great views and dog-friendly.You need bring only food and drink.Only 15 minutes into Front Royal for restaurants and near a dozen...
See all reviews
From
$195
Per Night
1 / 34
Payment Protection
Front Royal
3 Bedrooms, 5 Bathrooms, Sleeps 10
Bookings
Details Reviews (4) Make Inquiry Similar Properties
5 of 5 stars Reviewed July 7, 2014
As our host showed us around, demonstrating the sound systems, home theater, pinball machines, popcorn machine, kitchen gadgets, etc etc etc the jaws on our teenagers kept...
See all reviews
From
$195
Per Night
1 / 5
Payment Protection
Upperville
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry Similar Properties
From
$275
Per Night
1 / 24
Payment Protection
Front Royal
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Details Reviews (2) Make Inquiry Similar Properties
5 of 5 stars Reviewed October 21, 2014
Six of us stayed at this house for a long weekend. It's a big, beautiful house from the outside and inside. There is plenty of room and it's very inviting. Fyi...one of the...
5 of 5 stars Reviewed August 1, 2014
Wayne was super communicative, and his house is incredible. Warm decor, very spacious, and suited my party of 7 perfectly, with couch space to spare.
See all reviews
From
$345
Per Night
1 / 13
Payment Protection
Berryville
4 Bedrooms, 2 Bathrooms, Sleeps 16
Booking
Details Make Inquiry Similar Properties
From
$295
Per Night
1 / 10
Payment Protection
Berryville
3 Bedrooms, 2 Bathrooms, Sleeps 13
Details Make Inquiry Similar Properties
Get the List
From
$395
Per Night
1 / 9
Payment Protection
Berryville
6 Bedrooms, 3 Bathrooms, Sleeps 19
Booking
Details Make Inquiry Similar Properties
From
$199
Per Night
1 / 22
Front Royal
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Inquiry Similar Properties
From
$175
Per Night
1 / 14
Payment Protection
Dryfork, WV
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Details Make Inquiry Similar Properties
From
$99
Per Night
1 / 6
Harpers Ferry, WV
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (1) Make Inquiry Similar Properties
4 of 5 stars Reviewed September 11, 2013
This is a convenient 1 bedroom house about 1 mile from downtown Harpers Ferry. Parking is available. There is a deck and a yard. It's cozy and quiet. The only reason it did not...
See all reviews
From
$200
Per Night
1 / 1
Harpers Ferry, WV
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Reviews (3) Make Inquiry Similar Properties
5 of 5 stars Reviewed July 5, 2014
we were extremely happy with this rental..it was secluded yet close enough to walk to everything we wanted to see..The house was clean and everything we needed was provided. We...
5 of 5 stars Reviewed July 21, 2012
Beyond our expectations and worthy of many returns. We couldn't have asked for a better location or the views.
See all reviews
From
$150
Per Night
1 / 4
Harpers Ferry, WV
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (1) Make Inquiry Similar Properties
4 of 5 stars Reviewed August 11, 2013
The house had the feel of historic Harpers Ferry with all the amenities we were looking for. Fast wi-fi, huge kitchen and living space and a huge backyard. The front porch full of...
See all reviews
From
$200
Per Night
1 / 6
Harpers Ferry, WV
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Reviews (2) Make Inquiry Similar Properties
5 of 5 stars Reviewed September 20, 2012
At the risk of this place being unavailable next time I want it, I would like to say that it was everything I was looking for. I needed 2) walking distance to AT Conservatory and...
See all reviews
From
$36
Per Night
1 / 19
Linden
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry Similar Properties
From
$195
Per Night
1 / 33
Delaplane
3 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Inquiry Similar Properties
From
$275
Per Night
1 / 11
Toms Brook
4 Bedrooms, 3 Bathrooms, Sleeps 9
Details Make Inquiry Similar Properties
From
$58
Per Night
1 / 22
Front Royal
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Inquiry Similar Properties
From
$175
Per Night
1 / 12
Front Royal
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry Similar Properties
This feature is currently in development. Please try again later.
Go to map view
Book Online(12)
Use filters to find the best results!

Suitability

  • Wheelchair access (0)
  • Elder access (6)
  • Suitable for children (12)
  • Pet friendly (12)
  • Smoking allowed (1)

Amenities

  • Air Conditioning (20)
  • Other outdoor space (20)
  • Washer/Dryer (16)
  • Grill (15)
  • Internet (15)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Filter search results by:
Book Online(12)

Suitability

  • Wheelchair access (0)
  • Elder access (6)
  • Suitable for children (12)
  • Pet friendly (12)
  • Smoking allowed (1)

Amenities

  • Air Conditioning (20)
  • Other outdoor space (20)
  • Washer/Dryer (16)
  • Grill (15)
  • Internet (15)
  • View all amenities