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Cottages and Self Catering in Winchester, VA and nearby

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    1 / 71
    5 of 5 bubbles (2) Excellent
    Winchester
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    1 / 11
    5 of 5 bubbles (5) Excellent
    Winchester
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 20
    4 of 5 bubbles (1) Very good
    Winchester
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    The following rentals are within 25 miles of Winchester, Virginia.

    1 / 52
    4.5 of 5 bubbles (7) Very good
    Front Royal
    4 Bedrooms, 5 Bathrooms, Sleeps 26 | Quick View
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    • Wi-Fi
    • Mountain Views
    • Satellite TV
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    If you’re looking for the ultimate destination for your upcoming girlfriend’s getaway, family gathering, corporate retreat, bridal event or wedding, you can’t go wrong with the Celebration® retreat. Situated on 5 private acres of gorgeous land in Virginia’s wine country, 'Celebration® Retreat'... View all property information
    Location Information
    Front Royal, Virginia 22630
    5 of 5 bubbles Reviewed August 17, 2016
    We had an incredible experience for our group! The retreat is very clean and the indoor & outdoor amenities are amazing! We loved the home theater and the pinball machines. The...
    5 of 5 bubbles Reviewed June 22, 2015
    The suites are beautifully furnished,the jacuzzi is relaxing & the kitchen is top of the line! We really enjoyed the theater & white robes! You leave feeling like a special type...
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    1 / 38
    5 of 5 bubbles (10) Excellent
    Harpers Ferry, WV
    4 Bedrooms, 2 Bathrooms, Sleeps 14 | Quick View
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    • Washer
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Internet Access
    • Mountain Views
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Harpers Ferry, West Virginia 25425
    5 of 5 bubbles Reviewed January 11, 2016
    A great place conveniently located close to historic Harpers Ferry. My wife and I invited our kids and their spouses here to enjoy an early Christmas. This was our first time...
    5 of 5 bubbles Reviewed September 9, 2015
    House is perfect location to Harpers Ferry, Rivers Riders, Many Historical places. Big House 4 B.R. 2 Baths for my siblings. Had a great time would do it again. Manager was...
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    1 / 18
    Wardensville, WV
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • DVD Player
    • Balcony
    • Grill
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wardensville, West Virginia 26865
    1 / 11
    5 of 5 bubbles (1) Excellent
    Harpers Ferry, WV
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Grill
    • Secure Parking
    • Outdoor Dining Area
    • Mountain Views
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    2 Bedrooms - 2 Full Bathrooms Check-in 4pm / Check-out 10am (may be flexible) This home features a large open living room, a full modern kitchen, laundry room, dining room (6 seat dining table), 2 bedrooms (queen size), 2 full bath, and a large deck with grill. Our second vacation home, our other... View all property information
    Location Information
    Harpers Ferry, West Virginia 25425
    5 of 5 bubbles Reviewed January 3, 2016
    Very cute townhouse with stylish decor and lots of nice touches like leaving snacks, k-cup coffees, and candles for renters' use. The owners also left a bottle of wine since we...
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    1 / 5
    5 of 5 bubbles (2) Excellent
    Harpers Ferry, WV
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Washer
    • Balcony
    • Satellite TV
    • Mountain Views
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    The Space<BR><BR>Enjoy your stay in our family home in Harpers Ferry. This house is well furnished, comfortable, open space overlooks mountains and river. <BR><BR>House is suitable for couples, families with children, group of friends.<BR><BR>Private driveway to accommodate 1 car. There is guest... View all property information
    Location Information
    Harpers Ferry, West Virginia 25425
    5 of 5 bubbles Reviewed August 19, 2016
    The house was well maintained and looks out to the mountains, as advertised. The owner was very helpful. We had a great time.
    5 of 5 bubbles Reviewed October 5, 2015
    This vacation was absolutely perfect and that is no small part to Jacki and this amazing rental. We only had a small window of time to enjoy the rental and wanted to arrive early...
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    1 / 25
    5 of 5 bubbles (6) Excellent
    Harpers Ferry, WV
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
    • Internet Access
    • Parking
    • Balcony
    • Satellite TV
    • Air Conditioning
    • Patio
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Cozy, quiet Potomac River location. Come and play on the river. Kayak, canoe, swim, water ski, tube, float, paddle board, or fish The sleeping quarters is a newly renovated detached garage converted into 2 level guest house. Located near Historic Harper's Ferry. This lovely waterfront bungalow... View all property information
    Location Information
    Harpers Ferry, West Virginia 25425
    5 of 5 bubbles Reviewed September 20, 2016
    The cottage was adorabable. The view of the river, and the sounds of nature were so relaxing. The location was a short drive to everything.
    5 of 5 bubbles Reviewed August 21, 2016
    My 14-year old grandson is a HUGE fishing enthusiast, and he had no problem catching fish here. The owners are VERY accommodating and friendly, the location along the Potomac is...
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    1 / 15
    4.5 of 5 bubbles (5) Very good
    Harpers Ferry, WV
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • Balcony
    • DVD Player
    • Wi-Fi
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Harpers Ferry, West Virginia 25425
    5 of 5 bubbles Reviewed June 15, 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
    3 of 5 bubbles Reviewed April 1, 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 for...
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    1 / 5
    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
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Markham, Virginia 22643
    1 / 33
    Maurertown
    3 Bedrooms, 2 Bathrooms, Sleeps 11 | Quick View
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    • Mountain Views
    • Grill
    • Washer
    • Outdoor Dining Area
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Step back in time when the pace was slower and much quieter. This log cabin features 3 bedroom, 2 full baths and 2 living rooms. Large lake, smaller pond, stream, and stone foundation barn, with over 9 acres to explore. The stone sunroom features a wood stove, bar, ceiling fan and large windows.... View all property information
    Location Information
    Maurertown, Virginia 22644
    1 / 27
    Toms Brook
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Waterfront
    • Internet Access
    • Satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    • Patio
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Oh, Shenandoah… As the traditional folk song depicts, there’s nothing quite like the natural beauty of the rolling Shenandoah River, which winds through the misty Appalachians of West Virginia and Virginia. Not only does this region boast a rich history and incredible natural beauty, it’s also a... View all property information
    Location Information
    Toms Brook, Shenandoah County 22660
    1 / 9
    5 of 5 bubbles (8) Excellent
    Summit Point, WV
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Satellite TV
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • ?
    About this property
    We are listed here on FlipKey/TripAdvisor just to gather reviews. Google us "Ruby Summit Point" to find us. <BR><BR>Stay in a wonderful 3 bedroom house in Summit Point just minutes from the track! Bought, renovated and furnished in winter 2014. Multiple garage spaces and honor tools. Outdoor... View all property information
    Location Information
    Summit Point, West Virginia 25446
    4 of 5 bubbles Reviewed April 15, 2016
    We really enjoyed our 1 night at Ruby Summit Point, great spot very close to the track. Planning to stay here whenever at Summit Point in the future.
    5 of 5 bubbles Reviewed March 24, 2016
    This is a wonderful home away from home while you are visiting the Summit Point raceway. We had a group of 3 adults (2 working on getting their racing credentials), 1 teenager...
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    1 / 15
    Linden
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Mountain Views
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    As the city fades in the distance and the mountains appear on the horizon, you’ll feel the tension melt from your shoulders. Welcome to Apple Mountain View Chalet, where the Blue Ridge Mountains meet the Shenandoah River. Just sixty miles from Washington, D.C. but worlds away from the everyday.... View all property information
    Location Information
    Linden, Virginia 22642
    1 / 21
    Front Royal
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • DVD Player
    • Air Conditioning
    • Mountain Views
    • Waterfront
    • Washer
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Rolling River Farm (com) Private 100 Acre Riverfront Paradise surrounded by water on three sides due to its location on a full bend in the legendary Shenandoah River. -Just one hour from Dulles Airport and the Washington Capitol Beltway -Just one and a quarter hours from Capitol Hill (believe it... View all property information
    Location Information
    Front Royal, Virginia 22630
    1 / 44
    5 of 5 bubbles (40) Excellent
    Front Royal
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Wi-Fi
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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          ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~... View all property information
    Location Information
    Front Royal, Virginia 22642
    5 of 5 bubbles Reviewed 2 weeks ago
    We couldn’t have chosen a better destination for our little getaway! As soon as we arrived, we were immediately impressed with how nice, clean and well-equipped the Rainbow View...
    5 of 5 bubbles Reviewed 3 weeks ago
    The cabin views are amazing! My family loved being here and really enjoyed the hot tub on the cool evenings! It's close to so many things to do that we plan to come back next year...
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    1 / 27
    5 of 5 bubbles (5) Excellent
    Front Royal
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Central Heating
    • Hot Tub
    • Washer
    • Patio
    • Mountain Views
    • DVD Player
    • Balcony
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Front Royal, Virginia 22642
    5 of 5 bubbles Reviewed 5 days ago
    What a view! this is our second visit to Valley Views. The cabin had everything you could think of. The owners provided our family with brochures on places to visit and...
    5 of 5 bubbles Reviewed 6 days ago
    Inside the charming cottage, on the outdoor porch or in the luxurious hot tub, the view of the mountains takes your breath away. We enjoyed cooking in the well equipped kitchen...
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    1 / 5
    Upperville
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • ?
    • ?
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    • x
    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... View all property information
    Location Information
    Upperville, Virginia 20184
    1 / 10
    Chester Gap
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • DVD Player
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Alexina’s Dream is a beautiful property located on sloping land over-looking beautiful Happy Bay and the Bay of Grand Case. A footpath leads directly from the villa down to Happy Bay beach and joins the public footpath over to the more commercialized Friar’s Bay Beach (it is a little hike).... View all property information
    Location Information
    Chester Gap, Virginia 97700
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    1 / 6
    Harpers Ferry, WV
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
    • Air Conditioning
    • Private Yard
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy historic Harpers Ferry and the Appalachian Trail. Marbrun House is within walking distance of lower historic downtown and you can be on the Appalachian Trail within minutes. This private entrance bed and bath includes coffee/tea service, refrigerator and microwave. We also offer shuttle... View all property information
    Location Information
    Harpers Ferry, West Virginia 25425
    1 / 17
    Shepherdstown, WV
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A charming three-bedroom home in historic downtown Shepherdstown, WV, with all of the modern amenities. Enjoy the convenience of walking to the local restaurants, art galleries, and antique shops. Stroll across the street to visit the Opera House or Shepherd University. All sorts of outdoor... View all property information
    Location Information
    Shepherdstown, West Virginia 25443
    1 / 9
    Harpers Ferry, WV
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Air Conditioning
    • Secure Parking
    • DVD Player
    • Waterfront
    • Washer
    • Private Yard
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Peace Ridge Farm is nestled in the Blue Ridge Mountains near the Shenandoah National Forest. Our home was built in 1833 and is on the trail to Antietam. Our property has access to a private quarry lake. Our place is close to Historic Harpers Ferry, Shepherdstown, and Antietam. Wineries, Shenandoah... View all property information
    Location Information
    Harpers Ferry, West Virginia 25425
    1 / 10
    Front Royal
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Satellite TV
    • DVD Player
    • Washer
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    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Front Royal, Virginia 22630
    1 / 12
    2 of 5 bubbles (1) Poor
    Front Royal
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Washer
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Our 9 cabins are located near Front Royal, Virginia, the Canoe Capital of Virginia and where Skyline Drive begins... Only 10 miles from downtown Front Royal and 10 miles off Interstate I-66 - and just 60 miles directly west of Washington, DC. Hot Tub Heaven Vacation Cabins, offer 9 cabins... View all property information
    Location Information
    Front Royal, Virginia 22630
    1 / 11
    4 of 5 bubbles (2) Very good
    Toms Brook
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Porch
    • Washer
    • Internet Access
    • DVD Player
    • Satellite TV
    • Waterfront
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This home is located directly on the Shenandoah River and backs up to the George Washington National Forest. It is located on ten acres and totally private, but just minutes away from many activities. The home was just completed and this is a new listing. When you are sitting on one of the three... View all property information
    Location Information
    Toms Brook, Shenandoah County 22660
    4 of 5 bubbles Reviewed June 20, 2016
    My group of 4 friends rented the Toms Brook house from Mon - Friday for a guys outing of relaxation, BSing, and some fishing. All were accomplished and we really enjoyed ourselves...
    4 of 5 bubbles Reviewed August 17, 2015
    Great house. Great location. Private and fun. The owner responded professionally and timely to our concerns during the stay. The house is modern and well appointed. Getting...
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    Winchester Flight and Weather Info
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    Dulles Intl Airport
    41.2 miles from Winchester
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