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.

Holiday Rentals in Winchester

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.
Check In Check Out
    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}
    View Map
    Price
    per night
    €164 Average
    €0€1,000+
    Suitability
    More filters
    All 17 Rentals in Winchester
    Sort by:
    Default
    Don't let other travellers get your favourite Winchester area holiday rental. You're so close to securing your perfect getaway. Book today.
    Winchester
    5 of 5 bubbles
    5 Reviews
    3 Bedrooms, Sleeps 8Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Winchester
    5 of 5 bubbles
    2 Reviews
    5 Bedrooms, Sleeps 14Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Winchester
    4 of 5 bubbles
    1 Review
    1 Bedroom, Sleeps 2Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    The following rentals are within 30 kilometers of Winchester.
    Front Royal
    5 of 5 bubbles
    46 Reviews
    2 Bedrooms, Sleeps 4Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Wi-Fi
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 15 February 2017
    The cabin was absolutely amazing. Cozy, comfortable and had everything you could possibly need . Most gracious hosts make your stay as easy as possible. Everything is just...
    Excellent of 5 bubbles
    Reviewed 2 January 2017
    Myself and my wife have stayed at Rainbow View on several occasions now. Every time we have stayed, it has been nothing less than perfect. This is the ideal getaway cabin...
    See all reviews
    About this property
    (To check availability & rates just click the "Book Now" button.)                                    Rainbow View Cabin             Warren County Conditional Use Permit 2012●10●01              Member: Shenandoah Lodging & Tourism Alliance          ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~...
    View all property information
    Location Information
    Front Royal, Virginia 22642
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Front Royal
    5 of 5 bubbles
    8 Reviews
    3 Bedrooms, Sleeps 6Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Mountain Views
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 4 days ago
    Valley Vista Cabin had everything this family of mom, dad, 3 teens and a 10-year-old wanted. Far more than what the image of a "cabin" conjures up, this idyllic location made...
    Excellent of 5 bubbles
    Reviewed 16 March 2017
    Are you looking for a unique vacation full of nature, stunning views, and fresh air, and most importantly great hospitality? Well, Valley Vista is where it is at! My boyfriend...
    See all reviews
    About this property
    <span class="italic">(This is a brand new listing for a property that we've just opened, so it has no reviews yet. If you'd like assurance that we are legitimate, caring hosts, please check the reviews on our other existing listing #430119 that's been in operation for 4 years. But then don't forget...
    View all property information
    Location Information
    Front Royal, Virginia 22642
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Summit Point, WV
    5 of 5 bubbles
    8 Reviews
    3 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Satellite TV
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    Reviewed 15 April 2016
    We really enjoyed our 1 night at Ruby Summit Point, great spot very close to the track. Planning to stay here whenever at Summit Point in the future.
    Excellent of 5 bubbles
    Reviewed 24 March 2016
    This is a wonderful home away from home while you are visiting the Summit Point raceway. We had a group of 3 adults (2 working on getting their racing credentials), 1 teenager...
    See all reviews
    About this property
    We are listed here on FlipKey/TripAdvisor just to gather reviews. Google us "Ruby Summit Point" to find us. <BR><BR>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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Front Royal
    4 Bedrooms, Sleeps 6Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Outdoor Dining Area
    • DVD Player
    • Satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *****This Property requires 24 hour notice to book****** Enjoy your next vacation in this luxurious mountain home. Located on 18 acres, this home offers 3,000 sq. ft. of log home luxury. Enjoy the outdoors on any one of the many porches or the back deck. Located minutes from Skyline Drive and...
    View all property information
    Location Information
    Front Royal, Virginia 22630
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Wardensville, WV
    1 Bedroom, Sleeps 6Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • DVD Player
    • Balcony
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 6
    Make Enquiry
    Front Royal
    4.5 of 5 bubbles
    11 Reviews
    2 Bedrooms, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Amenities & Details
    • Grill
    • Parking
    • Air Conditioning
    • Internet Access
    • Hot Tub
    • Mountain Views
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Location Information
    Front Royal, Virginia 22630
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Upperville
    2 Bedrooms, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Capon Springs, WV
    2 Bedrooms, Sleeps 8Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Outdoor Dining Area
    • Air Conditioning
    • Parking
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elevate your next retreat to the countryside when you stay at this adorable 2-bedroom, 1-bathroom High View vacation rental cabin. Offering 640 square feet of charming living space, accommodations for 8 guests, and a quaint bunk house perched on the hill, this West Virginia home is sure to leave...
    View all property information
    Location Information
    Capon Springs, West Virginia 26808
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 8
    Make Enquiry
    Bluemont
    2 Bedrooms, Sleeps 3Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Balcony
    • Parking
    • Patio
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Picturesque setting, amazing views and a unique historic cabin home in Virginia Wine Country! Close to Washington, D.C. but a world apart. Please read the entire description before making your inquiry. This is part of our expanded home, closed off with doors between your space and the owner's...
    View all property information
    Location Information
    Bluemont, Loudoun County 20135
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
    Make Enquiry
    Front Royal
    4.5 of 5 bubbles
    10 Reviews
    4 Bedrooms, Sleeps 18Quick View
    other travellers have booked this property
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 1 week ago
    Our family enjoyed the quiet seclusion of the retreat with all of it's great amenities. Shopping and convenience are not far away and the location is easy to get to. Tammy was...
    Very good of 5 bubbles
    Reviewed 1 week ago
    Overall this was a positive experience, but I do have some mixed feelings. I would rate 3.5 if I could. Pros: -The house is beautiful, especially the views and outdoors...
    See all reviews
    About this property
    If you’re looking for the ultimate destination for your upcoming girlfriend’s getaway, family gathering, corporate retreat, bridal event or wedding, you can’t go wrong with the Celebration® retreat. Situated on 5 private acres of gorgeous land in Virginia’s wine country, 'Celebration® Retreat'...
    View all property information
    Location Information
    Front Royal, Virginia 22630
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 18
    Make Enquiry
    Front Royal
    2 Bedrooms, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Washer
    • Outdoor Dining Area
    • Grill
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Greeted by 2 acres of beautifully of landscaped property in the heart of Virginia wine country, step inside to find your modern mountain oasis. Top of the line HVAC unit for comfort all day long, 42' LCD TV, 2 additional TV's in the house, 2 queen size beds, 2 complete bathrooms, 1 couch with love...
    View all property information
    Location Information
    Front Royal, Virginia 22630
    Holiday Rental House - 2 Bedrooms, Sleeps 4
    Make Enquiry
    Charles Town, WV
    2 Bedrooms, Sleeps 5Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a completely private 2 bedroom condo with your own private entrance, nothing in this unit is shared, it is all yours. The space boasts a master bedroom with a queen sized bed, large closet, nightstands, dresser and all new and clean sheets and blankets. The 2nd bedroom has a twin bed with...
    View all property information
    Location Information
    Charles Town, West Virginia 25414
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Charles Town, WV
    1 Bedroom, Sleeps 4Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely private 1 bedroom condo, located in the heart of Historic Downtown Charles Town very close to some of the best bars and restaurants in the area and above the future Front Porch Brewing Co. This unit is also within walking distance to Hollywood Casino, American Public University, Charles...
    View all property information
    Location Information
    Charles Town, West Virginia 25414
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Front Royal
    2 Bedrooms, Sleeps 6Quick View
    Check In Check Out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Satellite TV
    • DVD Player
    • Washer
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    List your property
    Owner log in