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

104 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
Showing 103: English reviews
Start your review of Old Waterstreet Inn
 Click to rate
Reviewed 1 December 2016

We stayed 2 nights in late September, 2016 and had a nice room and great breakfast both mornings. Great location for walking into historic areas. Some concern about the heat not being turned on this early in the season, but the room was comfortable. Parking is easy from the alley in back. We are not experienced in B&B's, but this...

Thank Bill T
Indianapolis, Indiana
Reviewed 21 November 2016

What a wonderful little B&B in a super cool little town! It is Bed and Breakfast's like these that spoil you for some of the less fabulous ones. House was full but BEYOND quite at night! Bed was luxurious (sorry we were 1-2 weeks short of getting to enjoy the wood burning fire place in our room). Hosts were gracious...

1Thank leashmal
North Hero, Vermont
Reviewed 8 September 2016

Excellent hosts, accommodations and food. We stayed in Mr. Moore's Study and found it clean and comfortable. We walked to the Historic District and the city center. Great place to relax and enjoy Winchester, VA

1Thank holidayharbor
Rockville, VA
Reviewed 7 August 2016

Just came back from three days (two nights) at the Old Waterstreet Inn. Jeannie handled our reservations very well. Due to an unexpected family situation, she was not able to be there to welcome us upon arrival. She did, in fact, call and text ahead of time to alert us of this, allow us an earlier check-in, left a key,...

1Thank JandRRockville_VA
Reviewed 6 August 2016 via mobile

A lovely B&B, this has been our fourth stay at the beautiful restored home and each stay was delightful. The rooms have been lovely with a comfortable bed and bathroom, also always very clean. The Inn is located in and excellent part of Old Winchester, easy walk to excellent restaurants and specialty shops. We love the outside patio with fresh...

1Thank Deborah H
Richmond, Virginia
Reviewed 1 August 2016

We were lucky enough to stay in the Cortland Room at this beautiful B&B. The room was absolute perfection! Jeannie was a wonderful host and even had a place for us to store our bikes. The proximity to downtown was perfect! I was also madly in love with the staircase.

1Thank aggiegrl7
Pittsburgh, Pennsylvania
Reviewed 1 August 2016

The Inn is gorgeous, with historic value and charm. Our room was clean, very pretty, and cozy. (It is not a foofy or a country-style place). We absolutely loved how the owners decorated, with a blend of modern and Victorian decor. And the space is light and airy. It was nice sitting outside near the trees and flower gardens. But...

1Thank Pauline314
Kalamazoo, Michigan
Reviewed 23 July 2016

The building is beautiful and very nicely decorated but the owner made us feel very uncomfortable. We were not allowed to use the front door, she was very picky about rules, the waste baskets weren't emptied. We were there four nights and she wanted us to sign up everyday for breakfast. We said we'll be there every day at 8:30...

1Thank Maggie B
bbjeanne, Owner at Old Waterstreet Inn, responded to this review

It is dismaying as an innkeeper when we work so hard and guests like these sisters choose to write this review. We were very busy while they stayed with us, and so we had a sign up sheet for breakfast , as I can't serve everyone at once. They told me the first day they would always eat at 8:30,...

West Chester, Pennsylvania, United States
Reviewed 22 July 2016

I would give this inn only 2 stars but the suite was nice and it is in a great location. However the owner is selling and clearly does not want to be in business anymore and it shows. She is very worried about how guests treat the property and has a long list of rules. There are notes everywhere telling...

Thank Debbie R
bbjeanne, Owner at Old Waterstreet Inn, responded to this review

I spoke at length to the husband when he called to book, and I explained to him that as a small inn, I don't stock non dairy items. We rarely get vegans, but we accommodate them the best we can. He still chose to book . He said she would bring her own eggs, although being vegan she would eat...

Arlington, Virginia
Reviewed 6 November 2015

We live in urban Northern Virginia, and my wife decided we should take a few days away from home in early November to see the autumn leaves in western Virginia. Through an online search, she found the Old Waterstreet Inn in Winchester. We booked the Winesap Room for two nights. The weather was with us -- it was mild and...

2Thank George M
bbjeanne, Owner at Old Waterstreet Inn, responded to this review

Thank you so much for the complimentary review, we appreciate it very much . It was a pleasure having you as our guests!

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)


  • Free Parking
  • Breakfast included
  • Free High Speed Internet ( WiFi )
Room types
  • 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: $161 - $224 (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