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Holiday Rentals in Upperville

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    Don't let other travellers get your favourite Upperville area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 29 Rentals in Upperville
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    Upperville
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Upperville
    7 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    The following rentals are within 30 kilometers of Upperville.
    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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    Rainbow View Cabin - Shenandoah Valley view & hottub1 / 45
    (61)Excellent
    Linden
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    It rained every day but there was so much to do indoors that it didn't dampen (excuse the pun) our spirits. A wonderful, charming cabin and a great vacation.
    Reviewed 11 August 2018
    The owners thought of everything. Notes all over explaining things. Left us a very nice bottle of wine as well. Also gave great recommendations on things to do and places to eat...
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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
    Linden, Virginia 22642
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Monet Suite, elegnt lrg 2rm suite/blcny in villa1 / 31
    (6)Excellent
    Purcellville
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Housekeeping Included
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2018
    Beautiful landscaping. Clean rooms. Comfortable. Lovely countryside. Great pool. Absolutely wonderful hostess! Thank you, Maud!
    Reviewed 28 May 2018
    We loved our weekend getaway. The suite was spacious and comfortable. The views were amazing! We loved sitting out on the balcony each evening just listening to the sounds of...
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    About this property
    Artist's Villa on over 12 manicured acres with spectacular views looking out on Blue Ridge Mountains, located in heart of Loudoun County wine country and equestrian estates, in quaint village of Philomont; charming, serene, country setting, with well maintained roads, an hour from Washington D.C....
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    Purcellville, Loudoun County 20132
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Turquoise room at Loudoun Valley Manor - near Leesburg off Route 91 / 28
    (3)Excellent
    Waterford
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Patio
    • Parking
    • Grill
    • Housekeeping Included
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 December 2017
    Hated to leave... beautiful place! Comfortable, clean & nice layout! A glass of wine or just relaxing outside watching the sunset... happy place & lovely owner.
    Reviewed 10 July 2017
    Olga gave us a warm and friendly welcome; our visit was more like visiting an old friend than simply a host at a bed and breakfast. The Turquoise room, and the whole manor, was...
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    About this property
    Turquoise room (loft) is one of the several cozy bedrooms that Loudoun Valley Manor (Bed and Breakfast) offers in a luxurious house conveniently located a quarter mile off Route 9, in the outskirt of Waterford, between Leesburg and Purcellville in Loudoun County, Virginia. Wonderful serene views of...
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    Waterford, Loudoun County 20197
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Golden Room at Loudoun Valley Manor near Leesburg1 / 29
    (4)Excellent
    Waterford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2018
    Our stay in the Golden Suite was very comfortable. Loudoun Manor has a lovely, picturesque country setting in Virginia farmland and wine country, but is very close to Dulles...
    Reviewed 7 July 2018
    Our brief stay at Loudon Valley Manor could not have been more enjoyable!! The expansive property is impressive! We were warmly greeted by Olga, our delightful Hostess, upon...
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    About this property
    Loudoun Valley Manor (Bed and Breakfast) offers several cozy bedrooms in a luxurious house conveniently located a quarter mile off Route 9, in the outskirt of Waterford, between Leesburg and Purcellville in Loudoun County, Virginia. Wonderful serene views of surrounding landscape. Each room has a...
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    Waterford, Loudoun County 20197
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sienna Room at Loudoun Valley Manor - off Route 9 near Leesburg1 / 25
    (1)Excellent
    Waterford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Parking
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2017
    Olga made us feel at home in this beautiful house. The room was very nice and comfortable. Breakfast was awesome. We had a blast, lots of fun stuff to do in the area. I would...
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    About this property
    Sienna room is one of the several cozy bedrooms that Loudoun Valley Manor (Bed and Breakfast) offers in a luxurious house conveniently located a quarter mile off Route 9, between Leesburg and Purcellville in Loudoun County, Virginia. Stay for business or leisure! The property is located on a...
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    Waterford, Loudoun County 20197
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Green room - suite at Loudoun Valley Manor1 / 25
    (1)Excellent
    Waterford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 October 2017
    Husband and I stay at Loudoun Valley Manor from Thursday, Sept 28th till Sat Sept 30th 2017. Our room was very clean, spacious and quite, Olga the owner made us feel at home...
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    About this property
    Green room (suite) is one of the several cozy bedrooms that Loudoun Valley Manor (Bed and Breakfast) offers in a luxurious house conveniently located a quarter mile off Route 9, in the outskirt of Waterford, between Leesburg and Purcellville in Loudoun County, Virginia. Wonderful serene views of...
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    Waterford, Loudoun County 20197
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Waterford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My B&B is close to Leesburg, Virginia. Quarter mile off Route 9. Close to Purcellville. Stay for business or leisure! The depictured room is one of several private rooms Loudoun Valley Manor (B&B) offers for guests. Over 20 wineries around. 50-minute drive from Washington, DC. 25 miles to Dulles...
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    Location Information
    Waterford, Loudoun County 20197
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    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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    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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    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 7 September 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 3 April 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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    Leesburg
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious house with a private fenced backyard with deck, patio, and mature trees. Several shopping centers nearby, close to the Greenway (toll road) Battlefield exit, less than a mile to Leesburg Airport (private airplanes), 10 minutes to Dulles International Airport, 5 minutes to Loudoun One. 1...
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    Location Information
    Leesburg, Loudoun County 20175
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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 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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    Front Royal, Virginia 22630
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Amenities & Details
    • Housekeeping Included
    • Mountain Views
    • Hot Tub
    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2018
    A charming and warm home and a great place for a family or friends to gather. Carla, the owner, is such a warm and accommodating hostess. I would highly recommend this home...
    Reviewed 14 July 2017
    The photos of this property do not do it justice. The house is huge and at no point did 8-12 people in the house feel like too many. The dining room seated our large party of 10...
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    About this property
    Blue Hill is a charming historic 5 bedroom country house on 36 acres of wooded land located in the Shenandoah Valley Wine Country in scenic and historic Clarke County, Virginia. Blue Hill is about an hour and a half west of Washington, DC. Blue Hill is ideal for: •Weekend Getaways •Vineyard...
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    Location Information
    Winchester, Virginia 22620
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Markham
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • 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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    Waterford
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Private Garden
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Inn At Waterford has 4 bedrooms and 2.5 baths, and sits on nine beautiful acres overlooking rolling hills and picturesque views. We are located near the historic village of Waterford in the heart of Northern Virginia horse and wine country. We are conveniently located fifty miles from...
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    Location Information
    Waterford, Loudoun County 20197
    Private Room - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Bluemont
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • 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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    Bluemont, Loudoun County 20135
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    Paeonian Springs
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the country for peace and quiet. Watch the sunrise or sunset on the porches as deer walk through the field. Enjoy the relaxation or visit the many wineries, breweries, distilleries in Loudoun country. Hiking, biking, country fairs, wonderful restaurants, attend weddings...do as little...
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    Paeonian Springs, Loudoun County 20129
    Private Room - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    Amenities & Details
    • Air Conditioning
    • Washer
    • Shared Garden
    • Porch
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 May 2016
    We spent four nights at Just Like Heaven Carriage House in Winchester and loved every minute! The cottage is equipped with all you need to relax and enjoy the solitude and...
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    About this property
    We use ALL organic non-scented cleaning products. Our home is within Winchester city limits but has the peacefulness of the country. If it's a quiet safe neighborhood you're looking for you've found it! The perfect spot to rest and regroup amongst nature. Come enjoy the beauty of the Shenandoah...
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    Location Information
    Winchester, Virginia 22601
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
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    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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    Restoration B&B -  Master Bed1 / 26
    (2)Excellent
    Paeonian Springs
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    My wife and I stayed here for our first anniversary and we had a blast! Vickie and Richard were terrific hosts and put together a wonderful and delicious breakfast for us...
    Reviewed 12 July 2018
    This was by far the best bed and breakfast my husband and I have ever stayed at. From the moment we arrived we felt like we were staying with friends . Vickie and Richard are...
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    About this property
    Escape to the country for peace and quiet. Watch the sunrise or sunset on the porches as deer walk through the field. Enjoy the relaxation or visit the many wineries, breweries, distilleries in Loudoun country. Hiking, biking, country fairs, wonderful restaurants, attend weddings...do as little...
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    Location Information
    Paeonian Springs, Loudoun County 20129
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Paeonian Springs
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Patio
    • Central Heating
    • Balcony
    • Hot Tub
    • Grill
    • DVD Player
    • Mountain Views
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the country for peace and quiet. Watch the sunrise or sunset on the porches as deer walk through the field. Enjoy the relaxation or visit the many wineries, breweries, distilleries in Loudoun country. Hiking, biking, country fairs, wonderful restaurants, attend weddings...do as little...
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    Location Information
    Paeonian Springs, Loudoun County 20129
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Restoration B&B - Washington Room1 / 22
    (1)Excellent
    Paeonian Springs
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 June 2018
    All the reviews on here are 100% accurate. We found this place by accident on a last minute search to make a wedding event an opportunity to also be a weekend get away for us...
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    About this property
    Escape to the country for peace and quiet. Watch the sunrise or sunset on the porches as deer walk through the field. Enjoy the relaxation or visit the many wineries, breweries, distilleries in Loudoun country. Hiking, biking, country fairs, wonderful restaurants, attend weddings...do as little...
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    Location Information
    Paeonian Springs, Loudoun County 20129
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Aldie
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Washer
    • Air Conditioning
    • Grill
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note that the minimum stay is 2 nights* Welcome to the 'House Above the Barn' at MEA Haven Farm, a working horse farm nestled in the rolling hills of Aldie VA only minutes from historic Middleburg, Upperville, Leesburg and other quaint townships in the heart of Virginia's Horse Country....
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    Location Information
    Aldie, Loudoun County 20105
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Warrenton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Housekeeping Included
    • Patio
    • Central Heating
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This private suite in a 1940-built home offers a great getaway for couples or solo adventurers vacationing in Virginia Horse Country. The area is thick with wineries, breweries, horseback riding, historic sites and natural splendor. The suite includes a full bedroom, walk-in closet with private...
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    Location Information
    Warrenton, Virginia 20186
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
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    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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    Warrenton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Private Garden
    • Grill
    • Housekeeping Included
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Thoughtful design and idyllic light make this room a perfect retreat for couples or solo adventurers in Virginia's Horse Country. Long hikes, quiet bike rides, horseback riding, wine tasting... Enjoy the best that the Piedmont region has to offer, and come home to peaceful privacy. The room is...
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    Location Information
    Warrenton, Virginia 20186
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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