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

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Price
    per night
    |||
    |||
    $0
    $306 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Payment
    Book Online
    View Map
    More filters
    loading...
    Don't let other travellers get your favourite Winchester area vacation rental. You're so close to securing your perfect getaway. Book today.
    Applied filters:
    Nearby
    Clear All
    1 / 11
    5 of 5 stars (5) Excellent
    Winchester
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    From
    $292
    / Night
    Payment Protection
    View Details
    View Details
    Winchester
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other traveller has booked this property
    From
    $278
    / Night
    Payment Protection
    View Details
    View Details
    Winchester
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
    other travellers have booked this property
    From
    $209
    / Night
    Payment Protection
    View Details
    View Details

    The following rentals are within 30 kilometres of Winchester, Virginia.

    Berryville
    3 Bedrooms, 2 Bathrooms, Sleeps 13 | Quick View
    From
    $411
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Porch
    • Mountain Views
    • Parking
    • Air Conditioning
    • Patio
    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
    Location Information
    Berryville, Virginia 22611
    1 / 24
    4.5 of 5 stars (4) Very good
    Front Royal
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    From
    $383
    / Night
    Payment Protection
    View Details
    View Details
    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
    Location Information
    Front Royal, Virginia 22630
    4 of 5 stars Reviewed 7 October 2015
    We stayed at this location during the weekend of the immense rainfalls. Couldn't have asked for a better location as 8 adults snuggled in to this inviting retreat. We had a...
    4 of 5 stars Reviewed 3 March 2015
    I rented this cabin with a group of friends for my husband's birthday. We had 8 guests staying overnight and we had another ten or so people come over during the day to celebrate...
    See all reviews
    1 / 36
    4.5 of 5 stars (6) Very good
    Front Royal
    3 Bedrooms, 5 Bathrooms, Sleeps 20 | Quick View
    other travellers have booked this property
    From
    $411
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Ideal for groups, small family gatherings or a romantic escape! The Celebration retreat is located just under an hours drive from Washington DC on 5 beautiful acres with breathtaking views! Escape the hustle & bustle of the city. Imagine stunning sunrises, sunsets, entertainment, amazing local... View all property information
    Location Information
    Front Royal, Virginia 22630
    5 of 5 stars Reviewed 22 June 2015
    The suites are beautifully furnished,the jacuzzi is relaxing & the kitchen is top of the line! We really enjoyed the theater & white robes! You leave feeling like a special type...
    5 of 5 stars Reviewed 7 July 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
    1 / 13
    3 of 5 stars (1) Average
    Berryville
    4 Bedrooms, 2 Bathrooms, Sleeps 16 | Quick View
    other travellers have booked this property
    From
    $480
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Air Conditioning
    • Patio
    • Washer
    • Mountain Views
    • Porch
    • Parking
    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
    Location Information
    Berryville, Virginia 22611
    3 of 5 stars Reviewed 6 December 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...
    See all reviews
    Upperville
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    $271
    / Night
    Payment Protection
    View Details
    View Details
    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
    Location Information
    Upperville, Virginia 20184
    Wardensville, WV
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    From
    $138
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • DVD Player
    • Balcony
    • Grill
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Traditional log cabin of 1br and 1ba with sleeping loft and queen futon. Newly renovated. Cable TV and WiFi included. Ice cold AC and wood stove. Full kitchen with electric stove/oven, and ice maker. Second refrigerator in basement - as well as washer and dryer. All linens supplied. Gas grill. Fire... View all property information
    Location Information
    Wardensville, West Virginia 26865
    1 / 9
    5 of 5 stars (5) Excellent
    Summit Point, WV
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $557
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Balcony
    • Satellite TV
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    We are listed here on FlipKey/TripAdvisor just to gather reviews. Google us 'Ruby Summit Point' to find us. Stay in a wonderful 3 bedroom house in Summit Point just minutes from the track! Bought, renovated and furnished in winter 2014. Multiple garage spaces and honor tools. Outdoor... View all property information
    Location Information
    Summit Point, West Virginia 25446
    5 of 5 stars Reviewed 13 November 2015
    We rented Ruby for the PCA Club Race Weekend and could not have been happier! 5 minutes away from Summit Point Raceway and you are sitting in the lap of luxury after having...
    5 of 5 stars Reviewed 1 August 2015
    I don't often take the time to write online reviews but our extended family (three-generations) had such a great weekend staying at Ruby Summit Point. It truly felt like home away...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Berryville
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    $230
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Air Conditioning
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This is a guest bedroom within the Civil War Union Guest House (also known as the Philip Sheridan Guest Cottage). The bedroom sleeps 2-4 people with a private bath. One queen bed, and one set of single bunk beds. Located in historic Berryville, VA on the site of a Civil War battlefield, and... View all property information
    Location Information
    Berryville, Virginia 22611
    1 / 12
    Front Royal
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    From
    $244
    / Night
    View Details
    View Details
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Washer
    • Parking
    • Grill
    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... View all property information
    Location Information
    Front Royal, Virginia 22630
    Front Royal
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $1,183
    / Week
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Patio
    • Satellite TV
    • DVD Player
    • Washer
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    At Skyline Ranch Resort, through family-friendly entertainment and activities, we strive to accommodate those of all ages. Be it horseback riding, the limitless amount of fun that our activities director plans for the children, to the ability to wade in our salt water walk-in pool, there’s... View all property information
    Location Information
    Front Royal, Virginia 22630
    Berryville
    6 Bedrooms, 3 Bathrooms, Sleeps 19 | Quick View
    other traveller has booked this property
    From
    $550
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Parking
    • Mountain Views
    • Air Conditioning
    • Porch
    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
    Location Information
    Berryville, Virginia 22611
    1 / 21
    Front Royal
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    From
    $277
    / Night
    View Details
    View Details
    Amenities & Details
    • Grill
    • DVD Player
    • Internet Access
    • Mountain Views
    • Waterfront
    • Washer
    • Air Conditioning
    • Satellite TV
    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
    Location Information
    Front Royal, Virginia 22630
    Linden
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $209
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Patio
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Mountain Views
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    As the city fades in the distance and the mountains appear on the horizon, you’ll feel the tension melt from your shoulders. Welcome to Apple Mountain View Chalet, where the Blue Ridge Mountains meet the Shenandoah River. Just sixty miles from Washington, D.C. but worlds away from the everyday.... View all property information
    Location Information
    Linden, Virginia 22642
    1 / 44
    5 of 5 stars (24) Excellent
    Front Royal
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    From
    $188
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Mountain Views
    • DVD Player
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    (To check availability & rates just click the 'Request Booking' button.)                                    Rainbow View Cabin             Warren County Conditional Use Permit 1012●10●01              Member: Shenandoah Lodging & Tourism Alliance... View all property information
    Location Information
    Front Royal, Virginia 22642
    5 of 5 stars Reviewed 4 weeks ago
    My fiance, myself, and our dog visited the cabin this past weekend and everything was amazing! Chris and Steve made sure everything that we could possibly need was readily...
    4 of 5 stars Reviewed 18 December 2015
    Had a wonderful stay at your cabin in the mountains of VA. The large landscape windows along the kitchen and dining space allow you to enjoy the spectacular views! We really took...
    See all reviews