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.

Old Waterstreet Inn

Show Prices
Enter dates for lowest prices
powered by PriceFinder
Prices from our online travel partners are not available
Our online travel partners don't provide prices for this accommodation, but we can search other options in Winchester
Check In Check Out
Show Prices
Management photos
Old Waterstreet Inn
View Map
{"widget":{"name":"ibex_photo_carousel","template":"ibex_photo_carousel__widget","dust":{"nav_controls":"ibex_photo_carousel__nav_controls"},"moduleList":["handlers"],"divClasses":"prw_rup prw_ibex_photo_carousel","js":{"handlers":"(ta.prwidgets.getjs(this,'handlers'))"}},"scriptFlags":null,"containerClass":null}
Add Photo Write a Review
Turn Your Opinions into Points!
Turn your opinions into JPMiles
Turn your opinions into PAYBACK Points
*You can enroll in only one programme at a time to earn rewards for reviews.
JPMiles / Payback Arrow

104 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
There are newer reviews for Old Waterstreet Inn
See the most recent reviews
Showing 103: English reviews
Ormond Beach, Florida
Reviewed 10 October 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...

1Thank Salt Water Diva
Pittsburgh, Pennsylvania
Reviewed 24 August 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...

1Thank gdl8347
Greensboro, North Carolina
Reviewed 17 July 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...

Thank slphilli
Alburgh, Vermont
Reviewed 6 June 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...

2Thank Judy H
Crozet, Virginia
Reviewed 24 May 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...

Thank 13cwm
Washington, DC
Reviewed 20 May 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.

Thank Christopher R
Chantilly, Virginia
Reviewed 15 May 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...

Thank erinzblonde
Naples, Florida
Reviewed 9 May 2014 via mobile

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...

Thank MichaelSherman
Bolton, United Kingdom
Reviewed 3 May 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...

Thank Philippa_BillS
Reviewed 31 March 2014

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!

Thank Elizabeth S

35 photos of this hotel

Traveller photos: See what travellers like you saw

All Traveller Photos (31)
Dining (5)
Hotel & Grounds (7)
View from Room (1)
Room/Suite (6)
Bathroom (1)
Other (11)

Management photos: Courtesy of the property manager

All Management Photos (4)
Hotel & Grounds (2)
Dining (1)
Other (1)
Check In Check Out
Hotels you might also like...
Travellers also viewed these Winchester hotels
0.6 km away
The George Washington A Wyndham Grand Hotel
7.4 km away
Country Inn & Suites By Carlson, Winchester
2.1 km away
Hilton Garden Inn Winchester
Hilton Garden Inn Winchester
#6 of 25 in Winchester
652 reviews
Show Prices
Show Prices
Show Prices
2.6 km away
Hampton Inn Winchester-North
Hampton Inn Winchester-North
#5 of 25 in Winchester
607 reviews
2.8 km away
Courtyard Winchester Medical Center
2.2 km away
Hampton Inn Winchester-University/Mall Area
Show Prices
Show Prices
Show Prices


  • Free Parking
  • Breakfast included
  • Free High Speed Internet ( WiFi )
Room types
  • Non-Smoking Rooms
  • Family Rooms
In your room
  • Air Conditioning
  • Free Internet
  • Free High Speed Internet ( WiFi )
  • Free Parking
  • Breakfast included
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 

Additional Information about Old Waterstreet Inn

Address: 217 W. Boscawen St, Winchester, VA 22601
Region: United States > Virginia > Winchester
Price Range: ₹ 7,388 - ₹ 10,279 (Based on Average Rates for a Standard Room)
Number of rooms: 5
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

Questions & Answers

Here's what travellers have asked, with answers from Old Waterstreet Inn staff and other travellers.
1 question
Ask a question
Fairfax, Virginia

See all questions (1)

Questions? Get answers from Old Waterstreet Inn staff and past guests.
Posting guidelines
Typical questions asked:
  • 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?

See which rooms travellers prefer

“All were lovely”
JandRRockville_VA, 7 Aug 2016 | Read review
“The Winesap Room on the second floor is beautiful and has great views.”
  • The staircase from our room to the first floor
  • View from our room
georgemF6460DV, 5 Nov 2015 | Read review
“The Inn is on a busy street, but we had no trouble sleeping.”
btaes1, 20 Sep 2015 | Read review
“Our room was great in every way. Judging from the community areas, dining room, and halls, I can only imagine that all the rooms would be just as nice.”
842melindab, 4 May 2015 | Read review
“The Braeburn room is the one we chose, very soft and dreamily comfortable bed!”
erinzblonde, 15 May 2014 | Read review
5 of 5