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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 28 Rentals in Upperville
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    Upperville
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    The following rentals are within 30 kilometers of Upperville.
    Rainbow View Cabin - ShenandoahValleyview & hottub1 / 45
    (53)Excellent
    Front Royal
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Valley Vista Cabin - ShenandoahRiver view & hottub1 / 27
    (12)Excellent
    Front Royal
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    NEW! 'Anny's Farm House' 4BR Round Hill Home1 / 24
    (1)Excellent
    Round Hill
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Satellite TV
    • Washer
    • Internet Access
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2017
    A family visiting from the UK, we had a glorious two week stay in the farm house.accommodation was a really good size and very well equipped, and so peaceful!A haven if you...
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    About this property
    Embrace the peace, quiet, and tranquility of the rolling Central Virginia hills when you and your companions stay at this completely renovated 4-bedroom, 2-bathroom late 19th Century vacation rental farmhouse that sleeps 7. Remodeled with elegance and charm, 'Anny's Farm House' is located in Round...
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    Location Information
    Round Hill, Loudoun County 20141
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    • Balcony
    • Satellite TV
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    Beautiful home in the heart of Old Town Winchester1 / 11
    (6)Excellent
    Winchester
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Internet Access
    • Patio
    • Air Conditioning
    • Washer
    • Shared Garden
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Beautiful historic home that has been lovingly restored, centrally located in a charming, historic town full of great restaurants and shops. What more could you want?
    Reviewed 10 December 2015
    Picture telling your best friend that you're bringing your family to stay for a week, but when you get there you find a note from your friend saying "I had to leave. Make...
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    About this property
    Step back in time with a stay in the historic, completely renovated Peter Miller house, esta. 1802. It is like having the run of your very own Bed and Breakfast in the heart of historic Old Town Winchester. The three bedroom (1 K, 1 Q & 2 F) home has been restored and furnished with antiques and...
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    Winchester, Virginia 22601
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Charles Town, WV
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • 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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    Charles Town, West Virginia 25414
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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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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    • Housekeeping Included
    • Mountain Views
    • Hot Tub
    • Waterfront
    • Satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 7 March 2016
    This house is amazing. From the beautiful land around it, to the spacious rooms that were beautifully furnished. We LOVED this location. Well worth the money.
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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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    Leesburg
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    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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    Location Information
    Bluemont, Loudoun County 20135
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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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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    Aldie
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Washer
    • Air Conditioning
    • Grill
    • Balcony
    • 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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    Aldie, Loudoun County 20105
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    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.<BR><BR>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...
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    Location Information
    Winchester, Virginia 22601
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Markham, Virginia 22643
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Monet Suite, elegnt lrg 2rm suite/blcny in villa1 / 26
    (4)Excellent
    Purcellville
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Housekeeping Included
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2017
    This was the perfect way to get away DC and be close to all of the local vineyards. Maud was an excellent host. This place provides everything you would need. A ton of space...
    Reviewed 11 May 2017
    I booked this for my son and his wife for their wedding night. They loved the suite as it was very spacious and enjoyed petting the horses nearby. A quick get away in the...
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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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    Location Information
    Purcellville, Loudoun County 20132
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Waterford
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Inn At Waterford is a 4 bedroom Bed and Breakfast Inn, 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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    Vista Magnifique, a private 50 acre mountain-top estate in wine country1 / 24
    (1)Excellent
    Hume
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Washer
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Hot Tub
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 June 2017
    The house is on top of a little hill but very easy to drive in and out. The arrival instruction from the management is very handy and we got in without any difficulties. The...
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    About this property
    My place is close to vineyards, mountains, parks and horse country. You’ll love my place because of beautiful mountain-top views, the attention to detail, large space, and the peace and quiet.. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry...
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    Location Information
    Hume, Virginia 22643
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Charles Town, WV
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • 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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    Celebration Retreat, a fun venue in Wine Country1 / 64
    (10)Very good
    Front Royal
    4 Bedrooms, 5 Bathrooms, Sleeps 25 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 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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    • 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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    TyroleanGardenSuite/prvt wiz patio in art villa1 / 17
    (2)Excellent
    Purcellville
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Garden
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 June 2017
    I spent three nights in Mauds comfortable and very tastefully arranged suite. Comfortable bed and bedding, beautiful views from both inside the suite and the large patio. Maud...
    Reviewed 29 May 2017
    I went there with my family, my husband and my little girl 16 months old. The owner was very nice, and she did everything to accommodate us, including toys for the baby. She did...
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    About this property
    Elegant ground floor furnished spacious suite with full bathroom; private entrance and deck with Adirondack seating with table looking our on magnificent views of Blue Ridge Mountains, pasture and pool, in artist villa located in the heart of Loudoun's wine and Virginia hunt and horse country....
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    Purcellville, Loudoun County 20132
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The Van Gogh Room in Private Villa1 / 15
    (2)Excellent
    Purcellville
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Patio
    • Satellite TV
    • Housekeeping Included
    • Private Garden
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2017
    I highly recommend this place to anyone. So very polite and outgoing. Beautiful view from our room. Anything we needed was taken care of. We are planning another trip and...
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    About this property
    Van Gogh's Room is an elegantly furnished spacious room with breathtaking views of the Blue Ridge Mountains and foothills in artist villa in Philomont, located in the heart of Loudoun's wine n Virginia hunt n horse country. Second kitchen is available upon special request for lite cooking, at an...
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    Location Information
    Purcellville, Loudoun County 20132
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Green room - suite at Loudoun Valley Manor1 / 21
    (1)Excellent
    Waterford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Parking
    • Satellite TV
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    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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    Location Information
    Waterford, Loudoun County 20197
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Turquoise room at Loudoun Valley Manor - near Leesburg off Route 91 / 28
    (2)Excellent
    Waterford
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Patio
    • Parking
    • Grill
    • Housekeeping Included
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 25 May 2017
    Loudon Valley Manor is a wonderful place to stay--clean, spacious, and nicely decorated. Olga is an outstanding host. Our party of six greatly enjoyed our stay in this beautiful...
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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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    Location Information
    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
    (1)Excellent
    Waterford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
    • Parking
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2017
    We stayed at this fairly new Inn over the weekend while on a quick get-away to wine country. The house and grounds are beautiful, and the host Olga is delightful and made us...
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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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    Location Information
    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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    • Air Conditioning
    • Private Garden
    • Mountain Views
    • Wi-Fi
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Rose Room is one of the rooms of The Inn At Waterford, a luxurious Bed and Breakfast Inn. The Inn At Waterford 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...
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    Location Information
    Waterford, Loudoun County 20197
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sienna Room at Loudoun Valley Manor - off Route 9 near Leesburg1 / 23
    (1)Excellent
    Waterford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Parking
    • Private Garden
    • 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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    Location Information
    Waterford, Loudoun County 20197
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Waterford
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Parking
    • 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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