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“Much better than a Holiday Inn...”

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Old Waterstreet Inn
Ranked #1 of 3 Winchester B&B and Inns
Naples, Florida
Level 4 Contributor
27 reviews
9 hotel reviews
common_n_hotel_reviews_1bd8 22 helpful votes
“Much better than a Holiday Inn...”
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 again if I ever come this way.

Glad I missed the Holiday Inn...

Stayed May 2014, travelled solo
Helpful?
Thank MichaelSherman
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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106 reviews from our community

Traveller rating
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Rating summary
  • Location
  • Sleep Quality
  • Rooms
  • Service
  • Value
  • Cleanliness
Traveller tips help you choose the right room.   Room tips (22)
Date | Rating
  • English first
  • French first
  • Any
English first
Bolton, United Kingdom
Level 3 Contributor
11 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 12 helpful votes
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 at the Inn about nearby attractions and Jeannie helped us with directions to our next destination and gave us a much needed map! Breakfast was wonderful and set us up for the drive to the next stop. Would recommend to anyone.

Room Tip: Rooms are all individual and all lovely, choose any!
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  • Stayed April 2014, travelled as a couple
    • Value
    • Location
    • Sleep Quality
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Helpful?
Thank Philippa_BillS
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Richmond
Level 1 Contributor
3 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 1 helpful vote
Reviewed 30 March 2014 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!

Stayed March 2014, travelled as a couple
Helpful?
Thank Elizabeth S
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Blacksburg, Virginia
Level 4 Contributor
29 reviews
9 hotel reviews
common_n_hotel_reviews_1bd8 6 helpful votes
Reviewed 17 December 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 player and a variety of genres of music in the first floor living room, which guests can pick from to enjoy. Each room at the Inn has a booklet that talks about the history of the Inn, local shops and restaurants, and specific information about the history of the individual room. Very helpful! The bathroom had full sized bottles of shampoo, conditioner and body wash. Unfortunately, the shower door collects water (which drips onto the floor) and the shower head isn't detachable / handheld. The breakfasts were delicious, generously portioned and different each morning. During our stay, we had fresh fruit with yogurt and granola, apple walnut pancakes, chicken sausage, almond-encrusted French toast, and basil egg frittata. She is happy to make reservations at local restaurants, and the place she recommended to us (One Block West) was exactly what we had in mind. I would highly recommend Old Waterstreet Inn!

Room Tip: We stayed in Mr. Moore's study, which is the only room downstairs, but we loved the wood panelin...
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  • Stayed December 2013, travelled as a couple
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
Thank SCM_VAMD
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
washington dc
Level 3 Contributor
11 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 6 helpful votes
Reviewed 7 November 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 and many restaurants and located in a beautiful well maintained neighborhood. We would definitely stay there again on a return visit to Winchester.

Room Tip: We stayed in the Courtlandt room. It was large and comfortable with a private porch. The private b...
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  • Stayed November 2013, travelled as a couple
    • Value
    • Location
    • Sleep Quality
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    • Cleanliness
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Helpful?
Thank MartyDL
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Duncansville, Pennsylvania
2 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
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...
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  • Stayed August 2013, travelled on business
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
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Helpful?
1 Thank tahoerunner1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Washington, DC
Level 3 Contributor
20 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 15 helpful votes
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
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
Thank Madqween
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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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 

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