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All 4 Winchester B&Bs / inns

Old Waterstreet Inn

217 W. Boscawen St, Winchester, VA 22601
Hotel amenities
Old Waterstreet Inn
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75 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 (15)
Date | Rating
  • English first
  • French first
  • Any
English first
2 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 2 weeks ago 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
12 reviews 12 reviews
5 hotel reviews
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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washington dc
Senior Reviewer
9 reviews 9 reviews
3 hotel reviews
5 helpful votes 5 helpful votes
5 of 5 stars Reviewed November 7, 2013

I selected the inn from a city website and we were not disapointed. The house was beautiful, well decorated to the period, and well taken care of. Our room was large and comfortable with a porch for relaxing. The owners were very cordial and the breakfast was quite good. The inn is just a short walk from the pedestrian thoroughfare... More

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Duncansville, Pennsylvania
2 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed September 7, 2013

I've stayed in this Inn several times over the years and have had an extremely satisfying experience every time. This house was restored from the baseboards up. It is a pleasure to explore the house and discover the differences in each of the rooms. There is a sitting area upstairs for reading or just relaxing. Only one suite has a... More

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Washington, DC
20 reviews 20 reviews
4 hotel reviews
15 helpful votes 15 helpful votes
5 of 5 stars Reviewed September 5, 2013

We spent one night in the Cortland Room, which was large and very clean. The bathroom is just outside in the hallway, and there are robes in the closet for your use. The bathroom is just for the Cortland room. If you are only staying one night, you might not have a choice of all the rooms because Jeannie gets... More

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Columbia, Maryland
Senior Reviewer
6 reviews 6 reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed August 18, 2013

We spent two nights last week in the Winesap Room, on the second floor. It is a very spacious room, with two comfortable reading chairs (unlike some other bed and breakfasts, which value preciousness over comfort). Everything was extremely clean. The innkeeper does an excellent job of anticipating the needs of her guests, because nearly everything we might reasonably have... More

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Poquoson, Virginia, United States
1 review
5 of 5 stars Reviewed August 17, 2013

We went to Winchester for our 20th Anniversary. The Old Waterstreet Inn is in a large, old, restored house. The pictures on line don't do it justice! We stayed in Mr. Moore's study, the only downstairs room. We had the whole house to ourselves both nights. The living room was spacious and comfortable, and there were snacks and drinks on... More

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Albany, NY
Senior Reviewer
6 reviews 6 reviews
6 hotel reviews
18 helpful votes 18 helpful votes
4 of 5 stars Reviewed August 12, 2013

Overall, a nice stay, but not wonderful. Stayed in the Cortland Room - in the back with a nice porch for sitting. Huge room, comfortable bed. Bathroom was private but I had to go down the hall a few feet to get there. There are no locks on the individual rooms, if that is an issue for you. Nice furnishings... More

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oldwaterstreet, Owner at Old Waterstreet Inn, responded to this review

Thanks for the compliments to our Inn. We appreciate that you chose us on your route as a stopover. Regarding the temperature of the room, yes, this particular room temperature will fluctuate when the door to the porch is open. The central air is running all the time, but having the door open causes the temperature to rise and fall.... More

15 reviews 15 reviews
8 hotel reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed August 9, 2013

As soon as we entered we felt at home. the service was really great, welcoming us and putting on the hot water jug straight away. We were the only ones staying one this particular night so the house was quite and spacious. Our room was very nice and big enough for two. There is great history on the block of... More

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Toronto, Canada
13 reviews 13 reviews
9 hotel reviews
19 helpful votes 19 helpful votes
5 of 5 stars Reviewed July 24, 2013

a lovely inn with gorgeous rooms, well appointed and a gorgeous living and dining communal area. It is perfectly located nearby to shops and many restaurants and Jeannie was very helpful despite being very busy. We were very happy with our choice and hope to visit again. Highly recommend this Inn. Shannon was very efficient in taking our reservation and... More

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Additional Information about Old Waterstreet Inn

Address: 217 W. Boscawen St, Winchester, VA 22601
Location: United States > Virginia > Winchester
Free High Speed Internet ( WiFi ) Free Parking
Hotel Style:
Ranked #2 of 4 B&Bs / Inns in Winchester
Price Range (Based on Average Rates): $$
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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