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Winchester Vacation Rentals

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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 15 Rentals in Winchester
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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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    Just Like Heaven Carriage House1 / 24
    (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 - Shenandoah Valley view & hottub1 / 45
    (61)Excellent
    Linden
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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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    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Mountain Views
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 1, 2018
    This was our third time at Valley Vista. We loved it, again. Great place for adults alone, or with kids. Every detail has been considered by the owners. Pluses include a great...
    Reviewed October 4, 2017
    This place is magical. From the time you wake up in the morning and look down on the beautiful views below, to wonderful sites and food during the day including the wineries, to...
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    About this property
    Welcome to this quiet mountaintop getaway in the Blue Ridge Mountains with magnificent views overlooking the Shenandoah Valley! Relax in the hot tub as you gaze out over the Shenandoah River glistening in the sunset, the Massanutten Range and the Alleghenies across the Valley. Get away to an...
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    Location Information
    Linden, Virginia 22642
    Holiday Rental House - 3 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 April 25, 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 July 25, 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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    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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    Front Royal, Virginia 22630
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Celebration Retreat, a fun venue in Wine Country1 / 64
    (16)Very good
    Front Royal
    4 Bedrooms, 5 Bathrooms, Sleeps 25 Quick View
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    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 7, 2018
    Just getting around to writing this review. We rented this property for a long term rental while scouting the area for a business last year. It has Beautiful views from the...
    Reviewed April 2, 2018
    We drove to the lovely little town of Front Royal, knowing nothing of the area. This house was on our destination list the past couple of years. We drove up the long and winding...
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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 25
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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
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 5, 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
    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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    Charles Town, WV
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Air Conditioning
    • Cable/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
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make your next family getaway even better when you stay at this 4-bed, 3-bath vacation rental house that sleeps 8 in Charles Town! Perched on the fairways of Locust Hill, this home boasts sweeping views of grassy hills, vibrant landscape, and an easy-going atmosphere unbothered by the city. Whether...
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    Location Information
    Charles Town, West Virginia 25414
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Charles Town, WV
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/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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    Charles Town, WV
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Patio
    • DVD Player
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Note that the homeowner lives on site, in a completely separate unit ** A peaceful West Virginia getaway awaits at this 1-bedroom, 1-bathroom vacation rental apartment in Charles Town! Accommodating up to 2 guests, with all of the comforts of home, this unit is idyllic for a couple traveling...
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    Location Information
    Charles Town, West Virginia 25414
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Kearneysville, WV
    1 Bedroom, 1 Bathroom, Sleeps 15 Quick View
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    100-acre natural spring, scenic campground, provides many recreational opportunities for visitors. Compound Historic Nature Preserve is also West Virginia premier parks for all seasons. Opportunities for visitors: Brand New Basic for now Camping under the stars (no restrooms & no bedrooms)...
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    Location Information
    Kearneysville, West Virginia 25430
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 15
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