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.

“Lovely weekend” 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
Jacksonville, Florida
Level Contributor
15 reviews
5 hotel reviews
common_n_hotel_reviews_1bd8 7 helpful votes
“Lovely weekend”
5 of 5 bubbles Reviewed 13 April 2012

We loved our trip to this lovely B & B. Jeannie was very helpful with reservations and the breakfasts were delightful. Our room was large and very comfortable. We enjoyed the sitting rooms, the one on the first floor and also the sun room. It was in a very convenient location, we walked everywhere. Great place to stay, we recommend it highly.

  • Stayed April 2012, 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 elaineweaver
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, 4 August 2012
Thank you! It is always a true pleasure having guests like you!
Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
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
JPMiles / PAYBACK
50

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
Bethesda MD
Level Contributor
10 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 11 helpful votes
1 of 5 bubbles Reviewed 11 April 2012

This place may be lovely, and we may even end up staying there as I write, but the purpose of this review is to warn you about the Old Waterstreet Inn if you book it as part a package.

We booked a morning balloon ride and a stay the night before at the Old Waterstreet Inn as part of a package deal with 1-800-Skyride, who package novelty tours. The catch? Balloon companies can only know if they're flying about 24-48 hours beforehand, depending on the weather. And the cancellation policy at the Old Waterstreet Inn? Eight days in advance.

This means that on the day - months ago - when we booked the package, we took a 75% chance on losing 100% of our hotel booking money. We will only get away with this if the weather is good on the balloon-company's first-option date after all, and with ballooning, it often take several rainchecks before you actually get to fly. The balloon company themselves has had many postponements this year owing to unsafe winds, and they have absolutely no problem with rainchecks - it's a routine part of booking balloon flights and anybody who packages balloon flights with an overnight stay would know that.

The Old Waterstreet Inn was blunt and unhelpful, and my conversation with the lady there consisted of multiple re-statements of their 8-day policy on her part. This is clearly not a business that is capable of (or interested in) handling package bookings of the type we made in good faith.

So did the Old Waterstreet Inn misrepresent its capabilities to 1-800-Skyride with the idea of getting some extra package-tour dollars now and dealing with the problems later? Did 1-800-Skyride deliberately mishandle the Old Waterstreet Inn's policies and book them for a type of service they could not possibly deliver? Or was there just a lot of cluelessness - and no customer focus - on both sides? I can't say, though my money would be on option (3). And I can say that the Old Waterstreet Inn was very unhelpful and totally uninterested on the phone, while 1-800-Skyride seems genuinely concerned and is trying to fix the problem as I type.

The bottom line is that Old Waterstreet Inn may offer a great boutique hotel experience for all I know, but they don't play well with others - and cannot be relied upon to take responsibility for any other related packaged activities you may have booked.

Small place, small business model, small picture - perhaps we should have known better. But we trusted the packaged arrangements (cost, about $600) and assumed that whatever might happen, the customer service picture would not be placed dead last. We were wrong.

Room Tip: Don't stay here if you might need to alter your booking dates at short notice.
See more room tips
  • Stayed April 2012, travelled as a couple
    • 1 of 5 bubbles
      Value
    • 1 of 5 bubbles
      Service
Helpful?
2 Thank JohnKBethesdaMD
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, 4 August 2012
This was a very unfortuante situation for us and for John. I spoke to the company who offered the packages and they took full responsibility for the miscommunication to the client. They knew that we had an 8 day out cancellation, which is typical of small inns. I in no way mislead the company, who apologized to me and did pay for the cancellation. John was very unhappy, rightfully so, but there was nothing I could say to make him see our perspective. We do work with other package companies, such as Virginia Bicycling, and have a very good relationship with them. But for Hot Air Balloon companies, unless they can gurantee the cancellation of the room, we don't work with them. As a small Inn, we simply can't absorb the lost income for last minute cancellations with no hope of rebooking.
Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Washington DC, District of Columbia
Level Contributor
5 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 bubbles Reviewed 15 March 2012

We recently stayed at the Old Waterstreet and had an incredible experience. The house has a ton of character and is right in old town Winchester...perfect location, and a quick walk to just about everything in downtown. The food was great. Most importantly though, Jeannie and Erik were exceptionally accomodating and went out of their way to ensure we had a special stay. Thank you both!

  • Stayed March 2012, 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 franz w
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Chesapeake, VA
Level Contributor
23 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 4 helpful votes
5 of 5 bubbles Reviewed 19 February 2012

We recently enjoyed a "delicious" wine tasting weekend with three other couples and our home base was the lovely Old Waterstreet Inn in Winchester, VA. Our hosts, Jeannie and Erik could not have been more accommodating. The house is exquisite --- charming, elegant, and yet NOT stuffy. Every room is beautifully decorated and very comfortable. Breakfasts were delightful and generous. Winchester may be small but it has a nice pedestrain mall and the historic district has many intriguing little shops. Dinners in town both nights were very good. Jeannie and Erik will gladly assist you in making reservations. One caution: Only one bedroom is equipped with television, but after a full day of wine tasting, shopping, dining, and good times with good friends, who cared?

Room Tip: Choose the Cottage Suite if you absolutely must have access to a television. It is the only room th...
See more room tips
  • Stayed February 2012, travelled with friends
    • 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 BeachHokie
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Womelsdorf, Pennsylvania
Level Contributor
26 reviews
6 hotel reviews
common_n_hotel_reviews_1bd8 26 helpful votes
5 of 5 bubbles Reviewed 5 January 2012

We had the opportunity to spend a few days at the Old Waterstreet Inn with a group of friends for the New Years Weekend. Jeannie and Erik are very welcoming and provide lovely accomodations. The Inn is conveniently located within walking distance of the pedestrian Mall which has a varied assortment of shops and restaurants. There is a lot of history in this town and plenty of interesting architecture to see. We were only here for a short time and found that we need to revisit this area to really see everything. The Old Waterstreet Inn is one place that we plan to visit again.

  • Stayed December 2011, travelled with friends
    • 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 Celticgal54
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
0.6 km away
The George Washington A Wyndham Grand Hotel
7.5 km away
Country Inn & Suites By Carlson, Winchester
2.1 km away
Wingate by Wyndham Winchester
Show Prices
Show Prices
Show Prices
2.8 km away
Courtyard Winchester Medical Center
2.2 km away
Hampton Inn Winchester-University/Mall Area
3.1 km away
aloft Winchester
aloft Winchester
#14 of 25 in Winchester
4.0 of 5 bubbles 466 reviews
Show Prices
Show Prices
Show Prices

Been to Old Waterstreet Inn? Share your experiences!

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
50
JPMiles / Payback Arrow
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 (per night): ₹ 7,491 - ₹ 10,422
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