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Winchester House Rentals

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    Don't let other travellers get your favourite Winchester area holiday rental. You're so close to securing your perfect getaway. Book today.
    10 Matching Rentals in the Winchester AreaView all 25 rentals
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    Charming Historic Home in Shenandoah Valley Wine Country near Skyline Drive1 / 71
    (4)Excellent
    Winchester
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    The following rentals are within 40 kilometres of Winchester.
    Valley Vista Cabin - Shenandoah River & Massanutten/Allegheny Mt view w/ hot tub1 / 27
    (14)Excellent
    Linden
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Celebration Retreat, a fun venue in Wine Country1 / 64
    (14)Very good
    Front Royal
    4 Bedrooms, 5 Bathrooms, Sleeps 25 Quick View
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    Adventure Inn - Historic Home with Hot Tub, close1 / 38
    (15)Excellent
    Harpers Ferry, WV
    4 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Internet Access
    • Mountain Views
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2018
    Bunch of guys having a reunion using the house as hq for breweries and paintball, amazing house overall
    Reviewed 24 October 2017
    The house was beautiful and comfortable for 10 adults all weekend. We were already talking about our next stay all weekend. This house has everything you could ask for and...
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    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...
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    Location Information
    Harpers Ferry, West Virginia 25425
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 14
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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
    • Cable/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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    Two Rivers Guest House. Walk to rivers, parks, downtown and restaurants1 / 15
    (5)Very good
    Harpers Ferry, WV
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    • Balcony
    • DVD Player
    • Wi-Fi
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 June 2015
    Great house very clean lovely views from the upper deck every thing we needed was supplied.Eric the owner was very helpful.Thanks Stephen Carter
    Reviewed 1 April 2015
    Very clean home. This rental is attached to another home and in a development. No living room and only DVD player in one room. This was not as advertised. Overall, not bad...
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    About this property
    Two Rivers Guest House is centrally located in a fun and relaxing location. Well equiped for all to enjoy. Walking distance to rivers, parks, downtown, restaurants, shops, and Harpers Ferry National Park. The property has a locked storage room to accommodate bikes, kayaks, and other recreational...
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    Location Information
    Harpers Ferry, West Virginia 25425
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ruby Summit Point - Your Home at the Track1 / 19
    (11)Excellent
    Summit Point, WV
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Cable/satellite TV
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 April 2018
    Great place to stay. The cottage is great. The beds are comfy. The shower is hot. The blueberry muffins are awesome. I secretly ate my roommates' muffins. The place is very...
    Reviewed 26 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...
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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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    Markham
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Terrace
    • Central Heating
    • Washer
    • Grill
    • Patio
    • Mountain Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quiet and serene, this Wine Country Retreat is an easy drive from DC. Enjoy the privacy and seclusion of this 4-BR, 8,000 sf home on 11+ acres overlooking the Blue Ridge. Gorgeous views, including from large deck! Perfect for couples, 'girls get-away' weekends, family gatherings, corporate...
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    Location Information
    Markham, Virginia 22643
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Upperville
    7 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Parking
    • Mountain Views
    • Grill
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern house with 6 adult bedrooms, 4 bathrooms, 1 kids' room, dining room, and extra large living/ 'great' room. Close to Middleburg, Bluemont, the Plains (wine country), biking, hiking, hunting, horseback riding, wine tasting, relaxing destination! Park in driveway (fits up to 5 vehicles). 2...
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    Location Information
    Upperville, Virginia 20184
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 14
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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 spring-fed pond and a private section of our unique historic cabin home in Virginia Wine Country! Close to Washington, D.C. but a world apart. Settle in to the original 1776 cabin, a 15x24' log room with enormous stone hearth fireplace and...
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    Location Information
    Bluemont, Loudoun County 20135
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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