We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
The latest reviews. The lowest prices. The perfect place to shop for hotels.

“Wonderful Place to Stay” 5 of 5 bubbles
Review of Old Waterstreet Inn

We can't find prices for this accommodation
Our online travel partners don't provide prices for this accommodation, but we can search other options in Winchester
Check In dd/mm/yyyy Check Out dd/mm/yyyy
Old Waterstreet Inn
Ranked #1 of 3 Winchester B&B and Inns
Duncansville, Pennsylvania
2 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
“Wonderful Place to Stay”
5 of 5 bubbles Reviewed 7 September 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 TV, but who needs a TV when there is so much else to look at? Off street parking is available. The hostess is always available with local information about restaurants and events. Can even get tickets if requested or make reservations. It is centrally located in Winchester and shopping is only a walk away. A must stay place!

Room Tip: All rooms are quiet, but if you need a little extra space, the Cottage Suite is the choice. It has...
See more room tips
  • Stayed August 2013, travelled on business
    • 5 of 5 bubbles
      Value
    • 5 of 5 bubbles
      Location
    • 5 of 5 bubbles
      Sleep Quality
    • 5 of 5 bubbles
      Rooms
    • 5 of 5 bubbles
      Cleanliness
    • 5 of 5 bubbles
      Service
Helpful?
1 Thank tahoerunner1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Write a Review

104 reviews from our community

Traveller rating
    86
    10
    4
    2
    2
See reviews for
5
78
8
4
Rating summary
  • Location
    5 of 5 bubbles
  • Sleep Quality
    4.5 of 5 bubbles
  • Rooms
    5 of 5 bubbles
  • Service
    4.5 of 5 bubbles
  • Value
    4.5 of 5 bubbles
  • Cleanliness
    5 of 5 bubbles
Traveller tips help you choose the right room.   Room tips (21)
Date | Rating
  • English first
  • French first
  • Any
English first
Washington, DC
Level Contributor
20 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 15 helpful votes
5 of 5 bubbles Reviewed 5 September 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 last-minute bookings for two nights, but that's fine. There were chocolates and a full water pitcher with glasses in our room when we arrived. The room had good air conditioning, which was good, because it was pretty hot when we were there.

The house is really lovely -- there are well-furnished common areas on each floor with books and CDs, and there are chairs outside in the backyard for lovely evenings. The stairway has gorgeous huge windows that let a ton of light into the house. There is a pantry with snacks, sodas and water, and enough room in the mini-fridge for any leftovers. Breakfast was tasty and not too heavy -- we had a fruit cup with yogurt on the side, then egg frittata, sausage for meat-eaters, and little muffins.

Jeannie sent a list of restaurant recommendations, which was really helpful, and she made reservations for us. There is parking in the back, but street parking is also available. It's a close walk to downtown, but it's a nice distance away so that it's not too loud when the bars get out. We had a lovely stay here!

  • Stayed August 2013, travelled as a couple
    • 5 of 5 bubbles
      Value
    • 5 of 5 bubbles
      Location
    • 5 of 5 bubbles
      Sleep Quality
    • 5 of 5 bubbles
      Rooms
    • 5 of 5 bubbles
      Cleanliness
    • 5 of 5 bubbles
      Service
Helpful?
Thank Madqween
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Columbia, Maryland
Level Contributor
15 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 8 helpful votes
5 of 5 bubbles Reviewed 18 August 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 wanted was already provided. There are also several public areas with music, books, and additional comfortable chairs and sofas.

Breakfasts were very satisfying -- highlights included apple cinnamon muffins and locally-sourced sausage one day, and french toast with almonds accompanied by chicken and apple sausage the next. The innkeeper knows how to make herself available to guests without interfering. She is also an excellent source of advice and directions to the various attractions in and around Winchester.

There was some minor traffic noise one night, since the room faces a main street in town, but it did not disrupt our sleep at all. That's a small price to pay for the location just a few blocks from the pedestrian mall, historical sites, and good restaurants. Besides, it's a delightful historical house in its own right.

All in all, we enjoyed our visit tremendously and found it very relaxing. We will certainly return the next time we stay in Winchester.

  • Stayed August 2013, travelled as a couple
    • 5 of 5 bubbles
      Value
    • 5 of 5 bubbles
      Location
    • 4 of 5 bubbles
      Sleep Quality
    • 5 of 5 bubbles
      Rooms
    • 5 of 5 bubbles
      Cleanliness
    • 5 of 5 bubbles
      Service
Helpful?
Thank Fareastern89
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Poquoson, Virginia, United States
Level Contributor
3 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 3 helpful votes
5 of 5 bubbles Reviewed 17 August 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 hand in the well-stocked pantry. There is a lot to see and do in Old Town Winchester, and several great restaurants within walking distance. We felt welcome and very much at home during our two nights. Alyssa was very accommodating and provided us with great breakfasts both mornings--more than we could even eat. She was willing to make reservations, offer suggestions, and directions around town. They even bought decaf when I told them I try to avoid caffeine. We will be back. The service, food, and friendliness have made the Old Waterstreet Inn our choice for lodging in winchester. Very highly recommended!

  • Stayed August 2013, travelled as a couple
    • 5 of 5 bubbles
      Value
    • 5 of 5 bubbles
      Location
    • 4 of 5 bubbles
      Sleep Quality
    • 5 of 5 bubbles
      Rooms
    • 5 of 5 bubbles
      Cleanliness
    • 5 of 5 bubbles
      Service
Helpful?
Thank rsayre55
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Albany, NY
Level Contributor
20 reviews
15 hotel reviews
common_n_hotel_reviews_1bd8 39 helpful votes
4 of 5 bubbles Reviewed 12 August 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 in the community rooms and there are snacks available in the evening. Great recommendations for dinner, and there are many restaurants within walking distance.

The temperature in the room seemed to have a mind of its own and there was no way that I could find to modify it (luckily, the temperature at night was cool). Some additions, such as a table on the porch so that I didn't have to put my coffee cup on the floor and a handle to the screen door to/from the porch would have been good.

Stayed August 2013, travelled solo
Helpful?
Thank Jeff059
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, 23 August 2013
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. The other rooms do not have porches and stay very steady, weather it's a/c or heat. The Cortland Room porch is best enjoyed spring and fall, and on cool summer mornings or evenings.
Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Level Contributor
95 reviews
18 hotel reviews
common_n_hotel_reviews_1bd8 35 helpful votes
5 of 5 bubbles Reviewed 9 August 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 land and in the house which you can read about in the information booklet provided in each room. The location is also in the centre of town with just a short walk down one block to the main restaurants, shops and bars. A great find!!

Room Tip: We stayed in the room called Mrs Moore's study which was beautiful.
See more room tips
  • Stayed August 2013, travelled with family
    • 4 of 5 bubbles
      Value
    • 5 of 5 bubbles
      Location
    • 4 of 5 bubbles
      Sleep Quality
    • 5 of 5 bubbles
      Rooms
    • 5 of 5 bubbles
      Cleanliness
    • 5 of 5 bubbles
      Service
Helpful?
Thank Livah5
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Toronto, Canada
Level Contributor
41 reviews
16 hotel reviews
common_n_hotel_reviews_1bd8 32 helpful votes
5 of 5 bubbles Reviewed 24 July 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 helping with the breakfast. A nice plus was a small kitchenette where one could keep one s own food cool and also a free service of tea, coffee, pop and water which was greatly appreciated.

Room Tip: We stayed in the winesap room which was gorgeous. It was well appointed and had a lovely strong shoe...
See more room tips
  • Stayed July 2013, travelled as a couple
    • 4 of 5 bubbles
      Value
    • 5 of 5 bubbles
      Location
    • 4 of 5 bubbles
      Sleep Quality
    • 5 of 5 bubbles
      Rooms
    • 5 of 5 bubbles
      Cleanliness
    • 5 of 5 bubbles
      Service
Helpful?
Thank Marion J
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Hotels you might also like...
Travellers also viewed these Winchester hotels
0.4 mi away
The George Washington A Wyndham Grand Hotel
1.7 mi away
Courtyard Winchester Medical Center
4.6 mi away
Country Inn & Suites By Carlson, Winchester
Show Prices
Show Prices
Show Prices
1.9 mi away
aloft Winchester
aloft Winchester
#14 of 25 in Winchester
4.0 of 5 bubbles 464 reviews
1.6 mi away
Hampton Inn Winchester-North
Hampton Inn Winchester-North
#5 of 25 in Winchester
4.5 of 5 bubbles 601 reviews
2.0 mi away
Sleep Inn & Suites
Sleep Inn & Suites
#9 of 25 in Winchester
4.0 of 5 bubbles 374 reviews
Show Prices
Show Prices
Show Prices

Been to Old Waterstreet Inn? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about Old Waterstreet Inn

Property: Old Waterstreet Inn
Address: 217 W. Boscawen St, Winchester, VA 22601
Region: United States > Virginia > Winchester
Amenities:
Hotel Style:
Ranked #1 of 3 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 

Is This Your TripAdvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing