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Old Waterstreet Inn

217 W. Boscawen St, Winchester, VA 22601
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89 Reviews from our TripAdvisor Community

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Traveler rating
    75
    8
    3
    1
    2
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3
67
8
4
Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    4.5 of 5 stars
  • Rooms
    5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    4.5 of 5 stars
  • Cleanliness
    5 of 5 stars
Traveler tips help you choose the right room.   Room tips (18)
Date | Rating
  • English first
  • French first
  • Any
English first
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    (89)
  • Mar-May only
    (31)
  • Jun-Aug only
    (24)
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    (20)
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    (14)
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Herndon
1 review
3 of 5 stars Reviewed 1 week ago

My husband and I have been visiting B&B's for almost 20 years so I think we've seen the good and the bad. This B&B is neither, we were not impressed. Our bathroom was separate from the room, which we knew ahead of time, but there were plumbing problems in that bathroom from the time we arrived. We were asked to... More 

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West Milford, New Jersey
Level Contributor
60 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 20 helpful votes
5 of 5 stars Reviewed July 22, 2015

A beautiful structure, conveniently located within walking distance of Old Town. The room and bed were comfortable and this was one of the rare instances where we did not bring our own pillows in from the car because their pillows were excellent. Breakfast was delicious and presented very nicely. We only wish that we had the time on this trip... More 

Was this review helpful? Yes 1
Crown Point, New York
2 reviews
5 of 5 stars Reviewed May 20, 2015

Great place, beautifully decorated, central location, terrific breakfast. We booked the room with a private terrace and the only issue (minor) was privacy, with a wall of windows in the B&B's common area overlooking the terrace. It was a quiet weekday so not a big issue.

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Woodbine, Maryland
Level Contributor
3 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed May 4, 2015

For our 33rd wedding anniversary, my husband and I booked two nights at the Old Waterstreet Inn. We arrived just before the streets were blocked off for the festivities. It was wonderful for two days to have no worries as the guests of the Inn with a beautiful (spotless!) room with art on the walls and books on the shelves,... More 

Was this review helpful? Yes 1
Level Contributor
32 reviews
10 hotel reviews
common_n_hotel_reviews_1bd8 17 helpful votes
5 of 5 stars Reviewed February 18, 2015

On short notice, we enjoyed a brief stay in Winchester, one of our favorite cities in VA. Our room was warm, cozy, very clean and oh what a bathroom! Jeannie made us feel welcome and cared for, and made sure we were set for dinner plans. This was part of our valentine weekend getaway, and the historic setting (but with... More 

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Asheville, North Carolina
Level Contributor
100 reviews
39 hotel reviews
common_n_hotel_reviews_1bd8 162 helpful votes
5 of 5 stars Reviewed October 10, 2014

A beautiful old home in the heart of the charming historic section of Winchester. The inn is perfectly located within a short walk of great shops, bars and restaurants. That is a huge advantage because there is so much to discover in downtown Winchester. The style of the house is architecturally unique, with high ceilings and an unusual ornate staircase... More 

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Pittsburgh, Pennsylvania
Level Contributor
28 reviews
5 hotel reviews
common_n_hotel_reviews_1bd8 17 helpful votes
5 of 5 stars Reviewed August 24, 2014

The Old Waterstreet Inn is a gem. It is very tastefully decorated and has obviously had a lot of tender loving care. As owners of an old home we know how tough it is to maintain the high standards that were very much in evidence throughout the B & B. The B & B has a great location in that... More 

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Greensboro, North Carolina
Level Contributor
16 reviews
6 hotel reviews
common_n_hotel_reviews_1bd8 8 helpful votes
5 of 5 stars Reviewed July 17, 2014

The Old Waterstreet Inn is a lovely 1840's home and innkeeper Jeanie is terrific! We stayed in the Braeburn Room in a comfortable bed. The home is decorated in perfect colors and furnishings, and breakfast was a delicious sausage and French toast. She made us reservations at La Nicoise, a couple of blocks away, where we had a delicious French... More 

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Alburgh, Vermont
Level Contributor
14 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 9 helpful votes
5 of 5 stars Reviewed June 6, 2014

The Old Waterstreet Inn is a beautiful and elegant home within easy walking distance of numerous good restaurants and points of interest. Our room (The Braeburn Room) was spacious, attractively decorated in soothing colors and clean, with a very comfortable bed, a sitting area for two, and a fireplace. Jeannie’s excellent breakfasts were served in a lovely dining room with... More 

Was this review helpful? Yes 2
Crozet, Virginia
Level Contributor
3 reviews
3 hotel reviews
5 of 5 stars Reviewed May 24, 2014

Lovely lodging in a historic home, very hospitable, excellent rooms & food. We will definitely be back for a longer stay. The innkeeper sent us a list of local restaurants ahead of our arrival so we could find something enticing and make reservations. We visited the Museum of the Shenandoah Valley and the adjacent Glen Burnie house and gardens. It... More 

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Amenities