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Winchester Vacation Rentals

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    $206 Average
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    Don't let other travellers get your favourite Winchester area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 16 Rentals in Winchester
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    Beautiful home in the heart of Old Town Winchester1 / 11
    (5)Excellent
    Winchester
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Charming Historic Home in Shenandoah Valley Wine Country near Skyline Drive1 / 71
    (3)Excellent
    Winchester
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Just Like Heaven Carriage House1 / 19
    (1)Very good
    Winchester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    The following rentals are within 30 kilometres of Winchester.
    Rainbow View Cabin - ShenandoahValleyview & hottub1 / 45
    (52)Excellent
    Front Royal
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Certificate of Excellence
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    Amenities & Details
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Wi-Fi
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    This was easy to book via trip advisor. This is a 5 star cabin with wonderful facilities and views to match. The area is full of great walks and attractions and a multitude of...
    Reviewed 4 weeks ago
    Truly enjoyed our stay at Rainbow View Cabin. Steve and Chris were exceptional hosts. Although we never had the need or opportunity to meet them, we knew they were just a text...
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    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          ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~...
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    Location Information
    Front Royal, Virginia 22642
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Valley Vista Cabin - ShenandoahRiver view & hottub1 / 27
    (11)Excellent
    Front Royal
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Mountain Views
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2017
    Had a wonderful weekend, at this cabin near Linden. Easy to get to, with great privacy and views when you get there. This was the best appointed resort property we have ever...
    Reviewed 19 July 2017
    My friends and I wanted to take a girls trip closer to home (we live outside of Baltimore) and I had never been to Shenandoah Valley. I am so glad that we picked the Valley...
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    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...
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    Location Information
    Front Royal, Virginia 22642
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bluemont
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    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, gorgeous natural swimming pool 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. Send an email and we can discuss your needs and long term rates....
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    Location Information
    Bluemont, Loudoun County 20135
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    Ruby Summit Point - Your Home at the Track1 / 19
    (10)Excellent
    Summit Point, WV
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Satellite TV
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2017
    I happened to find Ruby Summit point, when searching for a hotel when traveling north for my first motorcycle roadrace at Summit Point raceway in early 2016. (i have been racing...
    Reviewed 21 July 2017
    Going to Summit Point for a track event? Ruby is an amazing place to stay -- the new cottage is incredible, and you are only about 6 minutes to the track. The decor is modern...
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    About this property
    We are listed here on FlipKey/TripAdvisor just to gather reviews. Google us "Ruby Summit Point" to find us. The two story cottage is comprised of The Loft (King and Two Twins), the Full bedroom downstairs, a living area with sofabed and TV, a kitchenette, and a bathroom with separate shower...
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    Location Information
    Summit Point, West Virginia 25446
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Wardensville, WV
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    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...
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    Location Information
    Wardensville, West Virginia 26865
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Front Royal
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Washer
    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Grill
    • Outdoor Dining Area
    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...
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    Location Information
    Front Royal, Virginia 22630
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Capon Springs, WV
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Private Garden
    • Satellite TV
    • DVD Player
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly, renovated bungalow nestled just inside George Washington National Forest. Steps away from the historic Capon Springs Farms Resort. Just a short drive to hiking trails; fishing and kayaking are are also available at Cacapon River, Trout Pond and Warden Lake. Relax on the porch while listening...
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    Location Information
    Capon Springs, West Virginia 26823
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Charles Town, WV
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    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...
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    Location Information
    Charles Town, West Virginia 25414
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Charles Town, WV
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    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...
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    Location Information
    Charles Town, West Virginia 25414
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2BDRM Skyline Ranch Chalet Summer Vacation1 / 10
    (1)Excellent
    Front Royal
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Satellite TV
    • DVD Player
    • Washer
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 June 2017
    I stayed because I had a long stay in Front Royal for business, it was perfect. It had all the accommodations and was much nicer than staying at a hotel. I was even able to do...
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    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...
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    Location Information
    Front Royal, Virginia 22630
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Upperville
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    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...
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    Location Information
    Upperville, Virginia 20184
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    CelebrationR Retreat, a fun venue in Wine Country1 / 65
    (10)Very good
    Front Royal
    4 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2017
    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...
    Reviewed 17 April 2017
    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...
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    About this property
    If you’re looking for the ultimate, fun & luxurious destination for your upcoming getaway to wine country such as a girlfriend’s getaway, family gathering or boutique family wedding you can’t go wrong with the Celebration® Retreat LT rental or their membership program. They rent to only one...
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    Location Information
    Front Royal, Virginia 22630
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 18
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    Front Royal
    2 Bedrooms, Sleeps 4 Quick View
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    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...
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    Location Information
    Front Royal, Virginia 22630
    Holiday Rental House - 2 Bedrooms, Sleeps 4
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