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All 4 Winchester B&Bs / inns

Old Waterstreet Inn

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217 W. Boscawen St, Winchester, VA 22601
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Old Waterstreet Inn
Ranked #1 of 4 Winchester B&B and Inns
Certificate of Excellence 2014
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83 people have reviewed this hotel

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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
Pittsburgh, Pennsylvania
13 reviews 13 reviews
3 hotel reviews
7 helpful votes 7 helpful votes
5 of 5 stars Reviewed 1 week ago

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
16 reviews 16 reviews
6 hotel reviews
6 helpful votes 6 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
14 reviews 14 reviews
8 hotel reviews
9 helpful votes 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

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Crozet, Virginia
2 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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Washington, DC
3 reviews 3 reviews
3 hotel reviews
5 of 5 stars Reviewed May 20, 2014

We stayed at Old Waterstreet Inn the week end of May 10. Jeannie, the innkeeper, was very helpful giving us information about things to do and see and restaurant recommendations. The rooms and breakfasts are excellent. This was our second visit to the Inn. We will be back again.

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Chantilly, Virginia
1 review
5 of 5 stars Reviewed May 15, 2014

This lovely historic home has been carefully transformed into a delightful bed and breakfast. The innkeepers were gracious from the very beginning, helping me with room choices and weekend options over the phone. Check-in was a breeze, and we had a reservation for dinner within minutes. Old Town Winchester is literally two blocks away (we left our car in the... More

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Naples, Florida
17 reviews 17 reviews
6 hotel reviews
10 helpful votes 10 helpful votes
4 of 5 stars Reviewed May 9, 2014

On a fast drive from Naples Fl to Marblehead Ma--alone. Didn't want a highway evening😆 So I found this B&B on this site and decided to see Winchester. Neat old historic town with lots of pretty cool restaurants and pubs. The hosts were very nice and the Inn was a pretty walk from the downtown. Pretty cool I'd do it... More

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Bolton, United Kingdom
Senior Reviewer
8 reviews 8 reviews
5 hotel reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed May 3, 2014

Visited the Old Waterstreet Inn with my Husband as part of our US roadtrip. We were made very welcome by Jeannie and felt completely at home during our stay. The Inn is very well located close to the historic part of town and there are several lovely bars and restaurants within walking distance (5mins). There was lots of information available... More

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2 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed March 30, 2014 via mobile

Jeannie, the innkeeper, was very welcoming. Informative, helpful. Our room and bath super clean and a comfortable bed. Two inviting sitting rooms with different atmospheres. Delicious breakfasts. Perfect location for dining and walking through town. Definitely would visit again. Thank you Jeannie!

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Salisbury, Maryland
Senior Contributor
21 reviews 21 reviews
8 hotel reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed December 17, 2013

My boyfriend and I stayed here to celebrate our anniversary. Jeannie (the proprietor) was prompt in responding to my email inquiries, friendly without being nosy during breakfast, and accommodating to special requests. She had fires going in the fireplace at night, and the whole house was decorated with touches of Christmas (including a beautiful tree). There is also a CD... More

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Additional Information about Old Waterstreet Inn

Address: 217 W. Boscawen St, Winchester, VA 22601
Location: United States > Virginia > Winchester
Price Range (Based on Average Rates): $$

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Free High Speed Internet ( WiFi ) Free Parking
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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  • Can tickets for local attractions be purchased at the front desk?
  • Do you have to pay extra for a mini-fridge?
  • At what time does the pool open each day?

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