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Vacation Rentals in Winchester, VA and nearby

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All 22 Rentals in the Winchester Area
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From
$195
/ Night
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1 / 12
5 of 5 stars (2) Excellent
Winchester
3 Bedrooms / 3 Bathrooms / Sleeps 8
travelers have booked this property
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From
$125
/ Night
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1 / 11
Winchester
1 Bedroom / 1 Bathroom / Sleeps 2
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The following rentals are within 25 miles of Winchester, Virginia.

From
$210
/ Night
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1 / 15
4.5 of 5 stars (3) Very good
Harpers Ferry, WV
2 Bedrooms / 2 Bathrooms / Sleeps 6
travelers have booked this property
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$195
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1 / 34
5 of 5 stars (4) Excellent
Front Royal
3 Bedrooms / 5 Bathrooms / Sleeps 20
travelers have booked this property
Overview Reviews (4) Make Inquiry
Amenities & Details
  • Parking
  • Fireplace
  • TV
  • Dishwasher
  • Microwave
  • Gym
  • DVD Player
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Located just under an hours drive from Washington DC is your Celebration™ retreat awaiting for you on 5 beautiful acres with breathtaking views! Escape the hustle & bustle of the city. Imagine stunning sunrises, sunsets, entertainment, amazing local wines & adventurous activities in the... View all property information
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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...
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$195
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1 / 5
Upperville
2 Bedrooms / 2 Bathrooms / Sleeps 4
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Amenities & Details
  • Number Of Bedrooms
  • # Of Bathrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Cute cottage in the heart of Upperviile, VA where the country's oldest horse show takes place in June every year. The town is typical of historic Virginian villages and the countryside is protected from development. This property is a wonderful weekend getaway from the stresses of city life with... View all property information
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From
$345
/ Night
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1 / 13
3 of 5 stars (1) Average
Berryville
4 Bedrooms / 2 Bathrooms / Sleeps 16
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Amenities & Details
  • Stove
  • Patio
  • Refrigerator
  • Parking
  • Dishwasher
  • Microwave
  • Dryer
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Union General Philip Sheridan squared off with Confederate General Jubal Early in the Battle of Berryville, the battle line falling along a ridge just behind the spot where this beautifully restored guest house now sits. The Philip Sheridan Cottage is a four-bedroom, two-bath guest house on a... View all property information
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3 of 5 stars Reviewed December 6, 2014
Very clean and comfortable with well furnished bedrooms. No TV or WiFi. We stayed during a cold weather snap of Thanksgiving 2014 that included snowfall so that we could not...
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From
$295
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1 / 10
Berryville
3 Bedrooms / 2 Bathrooms / Sleeps 13
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Amenities & Details
  • Linens Provided
  • Dishwasher
  • Microwave
  • Patio
  • Porch
  • Air Conditioning
  • Parking
  • Mountain Views
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
John Wayne, the namesake of this quaint guest house, was among many esteemed guests to the Rosemont Estate during its rich 200 year history. The John Wayne Lodge, built in the early 20th century, is surrounded by rare, historic trees and is just a stone's throw from the battle lines of the Battle... View all property information
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From
$395
/ Night
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1 / 9
Berryville
6 Bedrooms / 3 Bathrooms / Sleeps 19
traveler have booked this property
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Amenities & Details
  • Air Conditioning
  • Books
  • Microwave
  • Mountain Views
  • Towels Provided
  • Linens Provided
  • Parking
  • Soap/Shampoo...
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Confederate General Jubal Early squared off against Union General Philip Sheridan in the Battle of Berryville, fought just a stone's throw away from where this beautifully restored guest house now sits. The Jubal Early Cottage is a six-bedroom, 2.5-bath guest house nestled in a secluded, mostly... View all property information
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From
$300
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1 / 38
5 of 5 stars (6) Excellent
Harpers Ferry, WV
4 Bedrooms / 2 Bathrooms / Sleeps 14
travelers have booked this property
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Amenities & Details
  • TV
  • Microwave
  • Hot Tub
  • Fireplace
  • DVD Player
  • Grill
  • Dishwasher
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Historic 4 bedroom home just outside of Harpers Ferry, West Virginia convenient to all Harpers Ferry, Charles Town, and Shepherdstown attractions. Just an hour from the Washington DC and Baltimore, MD beltways; 1 hour from Fairfax, Virginia (VA); relax amidst the Blue Ridge Mountains near... View all property information
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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...
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From
$275
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1 / 24
5 of 5 stars (2) Excellent
Front Royal
3 Bedrooms / 3 Bathrooms / Sleeps 8
travelers have booked this property
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Amenities & Details
  • # Of Bathrooms
  • Number Of Bedrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Beautiful mountain home located on 18 acres. There is $3,000 sq ft of living space! All log home. Prime location!!! Located next to Skyline Drive entrance and right down the road from Skyline Caverns. Also right down the road from a local tubing, kayak, and canoe rental shop and public river... View all property information
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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.
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From
$155
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1 / 44
5 of 5 stars (16) Excellent
Front Royal
2 Bedrooms / 1 Bathroom / Sleeps 4
travelers have booked this property
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Amenities & Details
  • Microwave
  • DVD Player
  • Stove
  • Dishwasher
  • Refrigerator
  • Grill
  • Washer
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
(To check availability & rates just enter your dates above.)           (Or on a smartphone click the 'Book Now' button.) Rainbow View Cabin                                                            Warren County Conditional Use Permit 1012-10-01                    Member: Shenandoah Lodging &... View all property information
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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...
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From
$179
/ Night
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1 / 14
Dryfork, WV
1 Bedroom / 1 Bathroom / Sleeps 2
traveler have booked this property
Overview Make Inquiry
Amenities & Details
  • Stove
  • DVD Player
  • Microwave
  • Washer
  • Hot Tub
  • Dishwasher
  • Parking
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
This luxurious log cabin was designed and built for exclusive use by couples. Whether you are a brand new couple or you are celebrating your 50th wedding anniversary - we'd love to have you spend time in our romantic cabin. We know how important it is to forget the stresses of everyday life and... View all property information
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From
$199
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1 / 22
Front Royal
3 Bedrooms / 2 Bathrooms / Sleeps 8
Overview Make Inquiry
Amenities & Details
  • Garage
  • Washer
  • Stove
  • Refrigerator
  • Fireplace
  • Gym
  • Dryer
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Rolling River Farm (com) Private 100 Acre Riverfront Paradise surrounded by water on three sides due to its location on a full bend in the legendary Shenandoah River. -Just one hour from Dulles Airport and the Washington Capitol Beltway -Just one and a quarter hours from Capitol Hill (believe it... View all property information
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From
$150
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1 / 4
4 of 5 stars (1) Very good
Harpers Ferry, WV
2 Bedrooms / 1 Bathroom / Sleeps 4
Overview Reviews (1) Make Inquiry
Amenities & Details
  • Dishwasher
  • Air Conditioning
  • TV
  • Microwave
  • Refrigerator
  • Grill
  • Ceiling Fans
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
For up-to-date calendar and to book www.harpersferryvacationrentals.com Armory Quarters is a delightful step into the past. The house was built in 1820 to house the workers from the Armory. The house comfortably sleeps 4 with a queen and two twins and one bathroom. There is also a futon. To see up... View all property information
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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...
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$200
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1 / 6
5 of 5 stars (2) Excellent
Harpers Ferry, WV
2 Bedrooms / 2 Bathrooms / Sleeps 5
Overview Reviews (2) Make Inquiry
Amenities & Details
  • Dishwasher
  • TV
  • Washer
  • Grill
  • Dryer
  • Microwave
  • Parking
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
For up-to-calendar and to reserve www.harpersferryvacationrentals.com Moonshine Cottage is circa 1883. This house has a king-size bed, a queen, and pull-out couch. There are two full bathrooms. This house has a lovely claw-foot tub as well as separate shower. House includes washer and dryer. There... View all property information
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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...
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$200
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1 / 1
4.5 of 5 stars (3) Very good
Harpers Ferry, WV
2 Bedrooms / 2 Bathrooms / Sleeps 5
Overview Reviews (3) Make Inquiry
Amenities & Details
  • Dishwasher
  • Parking
  • Refrigerator
  • Grill
  • Fireplace
  • Dryer
  • Ceiling Fans
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
For up-to-date calendar and booking www.harpersferryvacationrentals.com The Butler Burrell House is a charming 1890s house. The property allows you to step back in time with the history of Harpers Ferry while enjoying modern amenities. You are within blocks of ghost tours, restaurants, shops, the... View all property information
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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.
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From
$99
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1 / 6
4 of 5 stars (1) Very good
Harpers Ferry, WV
1 Bedroom / 1 Bathroom / Sleeps 2
Overview Reviews (1) Make Inquiry
Amenities & Details
  • Dryer
  • Refrigerator
  • Porch
  • Satellite TV
  • Air Conditioning
  • Stove
  • Microwave
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
For up-to-calendar and to reserve www.harpersferryvacationrentals.com Canal House Cottage is a romantic one-bedroom cottage for nightly rent. The cottage is equipped with a full kitchen, AC, large deck and yard, Jacuzzi tub, and washer and dryer. Cottage sits amidst tall trees and has views of... View all property information
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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...
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From
$175
/ Night
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1 / 12
Front Royal
2 Bedrooms / 2 Bathrooms / Sleeps 4
Overview Make Inquiry
Amenities & Details
  • Dryer
  • Parking
  • DVD Player
  • Washer
  • Grill
  • Hot Tub
  • Microwave
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Our 9 cabins are located near Front Royal, Virginia, the Canoe Capital of Virginia and where Skyline Drive begins... Only 10 miles from downtown Front Royal and 10 miles off Interstate I-66 – and just 60 miles directly west of Washington, DC. Hot Tub Heaven Vacation Cabins, offer 9 cabins... View all property information
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From
$36
/ Night
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1 / 19
Linden
2 Bedrooms / 1 Bathroom / Sleeps 4
Overview Make Inquiry
Amenities & Details
  • VCR
  • Fireplace
  • Ceiling Fans
  • Dishwasher
  • Stove
  • Grill
  • Stereo System
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Blue Ridge Mountain Top Cabin with breathtaking views of the Shenandoah River, Shenandoah Valley, Mountain Ranges, amazing sunsets and bright starry nights. ONLY ACCEPTING MONTHLY RENTALS AT THIS TIME... Only minutes from Fox Meadow, Barrel Oak, Naked Mountain, Chateau O' Brian, Linden... View all property information
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From
$58
/ Night
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1 / 22
Front Royal
3 Bedrooms / 2 Bathrooms / Sleeps 8
Overview Make Inquiry
Amenities & Details
  • Stove
  • Dishwasher
  • Microwave
  • Refrigerator
  • Stereo System
  • Ceiling Fans
  • Patio
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
**THIS PROPERTY IS AVAILABLE FOR MONTHLY RENTAL OR LONGER** AspenHill Cottage is a charming 3 bedroom 2 full bath home with 2 levels of living space located on 2 acres in the beautiful Shenandoah Valley. It has lovely forest and mountain views overlooking the Shenandoah River Area. The... View all property information
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From
$275
/ Night
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1 / 11
Toms Brook
4 Bedrooms / 3 Bathrooms / Sleeps 9
Overview Make Inquiry
Amenities & Details
  • DVD Player
  • Dryer
  • Stove
  • Fireplace
  • Stereo System
  • Dishwasher
  • Grill
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This home is located directly on the Shenandoah River and backs up to the George Washington National Forest. It is located on ten acres and totally private, but just minutes away from many activities. The home was just completed and this is a new listing. When you are sitting on one of the three... View all property information
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From
$195
/ Night
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1 / 33
Delaplane
3 Bedrooms / 1 Bathroom / Sleeps 6
Overview Make Inquiry
Amenities & Details
  • Microwave
  • Washer
  • DVD Player
  • Air Conditioning
  • Fireplace
  • Grill
  • Parking
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Step back in time while staying at the enchanting and contemporized Moreland Cottage. This home was built at the turn of the 19th Century and underwent a full restoration and modernization in 2011, keeping the charm of the original log, wood and stone home while updating it with amenities such as... View all property information
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