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“A Most Comfortable Spot” 4 of 5 stars
Review of Old Waterstreet Inn

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Old Waterstreet Inn
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217 W. Boscawen St, Winchester, VA 22601   |  
Hotel amenities
Ranked #1 of 4 Winchester B&B and Inns
Certificate of Excellence 2014
Bethesda, Maryland
Senior Contributor
45 reviews 45 reviews
3 hotel reviews
Reviews in 21 cities Reviews in 21 cities
12 helpful votes 12 helpful votes
“A Most Comfortable Spot”
4 of 5 stars Reviewed October 22, 2012

This upscale, beatifully restored B&B just off the center of this well-kept and historic town is beautifully propotioned inside, with high ceilings, generously-sized bedrooms, two sitting romms and a pantry where you can make your own hot beverages, keep your wine cool and pick up complimentary snacks.
It is within walking distance of just about everything in Winchester, there is off-street parking and a garden to sit out in.
Jeannie, your host, prepares interesting breakfast dishes and will help you with restaurant reservations and local information.
We were there to play golf and we played at Rock Harbor, 10 minutes away, and enjoyed it - a course with some unusual and challenging holes, undulating fairways, a good deal of water, spectacular rocks and resaonable green-fees.

Room Tip: Rooms vary in cost and size so book early and make sure you get the one that suits you best. Most ro...
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  • Stayed October 2012, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 4 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
oldwaterstreet, Owner at Old Waterstreet Inn, responded to this review, October 24, 2012
We very much appreciate you complimentary review. Glad that you enjoyed the two sitting rooms, and the yard/terrace - great spaces to relax I think!
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85 reviews from our community

Traveler rating
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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 (17)
Date | Rating
  • English first
  • French first
  • Any
English first
Williamsburg, Virginia
Senior Reviewer
8 reviews 8 reviews
3 hotel reviews
Reviews in 7 cities Reviews in 7 cities
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed September 29, 2012

My wife and I stayed here recently for one night to break up our trip home. The inn is located on a side street in old town Winchester. Our room was beautifully wood panelled with a private bath. The room had both natural light and good reading lights. In addition, there was a downstairs communal living room and a wonderful sun room upstairs for other reading options. The breakfast was very good and freshly prepared. The inn has offstreet parking and is only a short walk from restaurants and museums in old town Winchester. The owner was very helpful with restaurant suggestions and directions. A very pleasant surprise and nice break to our trip. We will definately stay here again when in the Winchester area.

  • Stayed September 2012, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
oldwaterstreet, Owner at Old Waterstreet Inn, responded to this review, October 24, 2012
Thanks! yes, I think our location is perfect for enjoying Old Town, and I am always glad to make suggestions for dinner. We're lucky to have several great restaurant choices and good variety too, all within walking.
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Frederick, Maryland
Reviewer
4 reviews 4 reviews
3 hotel reviews
Reviews in 4 cities Reviews in 4 cities
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed August 14, 2012

A friend had recommended we go to Winchester for a little getaway. Not knowing much about the area I found the Old Waterstreet Inn on line and read the reviews. The b and b was absolutely stunning. Large, spacious, beautifully decorated, and charming. The location was perfect. Within walking distance of historic Winchester. Since we were the only guests, we the priviledge of viewing all the rooms and each and every one of them was charming and beautifully appointed. The hosts Jeanie and Erik were lovely. They were available for questions if we had any and offered fun suggestions of things to see, do, and eat in the area. The breakfast was ample and very delicious. Definetely worth a stay!

Room Tip: All the rooms are beautifully appointed. We stayed in the Brayburn room. The sage green color sche...
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  • Stayed August 2012, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Alexandria, Virginia
Reviewer
3 reviews 3 reviews
5 of 5 stars Reviewed June 26, 2012

I was looking for a quiet place where I could catch up on my reading and get refreshed. This was the perfect place. I stayed two nights in the Cortland room, which was very charming, as was the entire house. I especially liked the porch outside my room, where I spent most of the day reading. The only downside was that the private bathroom was not inside the room, but the porch was well worth it and made up for the less convenient bathroom. The breakfast each day was great. I enjoyed sitting at the large table in the dining room, getting to know some of the other guests.
It was my first time to Winchester. The Inn is conveniently located near all the restaurants and pubs. I will definitely go back again.

Room Tip: The Cortland room is located on the back side of the house and was very quiet. The porch was a grea...
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  • Stayed June 2012, traveled solo
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 4 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
oldwaterstreet, Owner at Old Waterstreet Inn, responded to this review, August 4, 2012
Thanks so much for your positive comments. Cortland is a lovely room, especially in warm months when you can enjoy the porch. It is perfect for relaxing and finding a little serenity.
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Alexandria, Virginia
1 review
5 of 5 stars Reviewed June 11, 2012

Two thumbs up for this historic house full of character and souther charn. We stayed in the Cortland Room- the room is huge and has a private bathroom. The best part was the private porch off our room. It is the perfect place to enjoy a glass of wine or a cup of coffee. The host is extremely hospitable and knowledgable about local restraunts, wineries and shopping. Breakfast was delicious! Don't think twice- make your reservation now!

  • Stayed June 2012, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
oldwaterstreet, Owner at Old Waterstreet Inn, responded to this review, August 4, 2012
Thanks so much! I try to keep up with what's going on locally, and we regularly eat out so we can receommend the best ones, whether it's fine dining or a cafe or a pub restaurant. We want our guests to have a great total experience in Winchester with a wonderful dinner and interesting things to do.
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Paw Paw, West Virginia
Top Contributor
101 reviews 101 reviews
39 hotel reviews
Reviews in 34 cities Reviews in 34 cities
68 helpful votes 68 helpful votes
5 of 5 stars Reviewed May 15, 2012

My wife and I stayed at the Old Waterstreet Inn on a get-a-way weekend. While the owners were away, they had a woman there who provided excellent hosting, and took care of all our needs. The Old Waterstreet Inn is the essence of hospitality. It is immaculate despite being an old building with the quirks of age. The breakfast was excellent. We will return.

Room Tip: The Cortland Room's bathroom off the hall, not the room. The web site lets you know this, but...
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  • Stayed May 2012, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Bethesda, MD
Top Contributor
176 reviews 176 reviews
19 hotel reviews
Reviews in 55 cities Reviews in 55 cities
40 helpful votes 40 helpful votes
3 of 5 stars Reviewed May 7, 2012

Best part of our stay was not having to drive anywhere for 2 days. This place is in walking distance of all the activities we enjoyed at a recent event. Room was large and my wife loved all the lamps. Bed was comfortable, but noise from the street was steady and significant. Sure would have liked to watch the news at night, but no tv in room. Breakfast was ordinary except for good juice & coffee. Hostess very friendly.

  • Stayed May 2012, traveled as a couple
    • 3 of 5 stars Value
    • 5 of 5 stars Location
    • 3 of 5 stars Sleep Quality
    • 3 of 5 stars Rooms
    • 3 of 5 stars Cleanliness
    • 4 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
oldwaterstreet, Owner at Old Waterstreet Inn, responded to this review, August 4, 2012
Thank you for your feedback. We do have a wonderful location in Old Town, but unfortunately that means we do get street traffic. generally it is not bad, and we do not get many complaints, since guests expect some noise when they are in the center of the town.

As for breakfast, I really am sorry it didn't meet your expectations. They had Almond Amaretto french Toast one day, and Smoked Gouda Asparagus Quiche the other, and these are two favorites of my guests.

Only one of our rooms has a television, and that is noted on our website. Some guests miss that for sure, but others feel it's a nice break from the routine of watching tv, and they tell me they read more, talk to each other more, and enjoy relaxing together.
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Additional Information about Old Waterstreet Inn

Address: 217 W. Boscawen St, Winchester, VA 22601
Location: United States > Virginia > Winchester
Amenities:
Hotel Style:
Ranked #1 of 4 B&Bs / Inns in Winchester
Price Range (Based on Average Rates): $$
Number of rooms: 5
Official Description (provided by the hotel):
A lovely 1840 home in the heart of Winchester's historic district. Walk to the quaint pedestrian street in Old Town, where you'll find shops, great restaurants, and nightlife. The casual elegance creates a charming, relaxed atmosphere. A full breakfast is included, as well as complimentary soft drinks, tea, and light snacks. Wine and cheese package available. ... more   less 

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