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Old Waterstreet Inn

217 W Boscawen St, Winchester, VA 22601-4117
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Dining (6)


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.
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Property amenities
Free parking
Free High Speed Internet (WiFi)
Free internet
Free breakfast
Non-smoking hotel
Room features
Air conditioning
Room types
Non-smoking rooms
Good to know
Centrally Located
113Reviews1Q+A26Room tips
Traveler rating
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Popular mentions
Kudos to owners Jeanne and Erik for creating this charming and comfortable B&B located a short walk from downtown Winchester’s lively pedestrian mall. We had a splendid overnight stay and look forward to our next visit.
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Was really hoping to find a B&B near the Old Town since we were attending the Blooming Wine Fest. I was able to book at Old Waterstreet Inn. Beautiful home and we opted for Mr. Moores Study, the smallest room in the house but it was enough. It provided a comfortable nights sleep. We weren't there to stay in the room. We were hoping to be within walking distance to the old town and we were. Our room was add on to the original house. It is right off the dining room and faces the street side. Since it was added on, no one above us making noise. And surprisingly the outside noise was minimal. Bed and pillows very comfortable. Beautiful furnishings and Jeanne was a great hostess. Did what she could to take care of some other guests with special dietary needs. Breakfasts were delicious. Jeanne only serves a small group at a time to make sure your breakfast is fresh and hot. Enjoyed our stay, 2 comfortable sleeps and delicious hot breakfast before heading off to the festival. We were able to go to the festival, walk some of our wine purchases back to our through out the weekend. It met our needs perfectly.
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My wife and I met up with her brother and his wife for the weekend, as Winchester was halfway between us. We had the inn all to ourselves and had a great time. Jeannie was a wonderfully accommodating hosts and the breakfasts were terrific. We couldn’t have picked a better place to stay for our family getaway.
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We had a wonderful stay with family. The Inn Keeper/Owner Jeanne was friendly. She was very helpful getting reservations made for us at a lovely restaurant downtown. She was very knowledgeable about the area and places for us to visit. Can't wait for our next stay at the Old Waterstreet Inn
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This B&B in historic Winchester Va, owned & run by Jeannie Faith, is within walking distance from the two-block pedestrian area of boutique shops, antique & art galleries, unique restaurants & coffee shops, and the Civil War Museum. Jeannie is warm & welcoming, house-proud & extremely accomodating! My husband & me & our daughter stayed in the Cottage Suite on the top floor of this wonderfully restored home! We loved the secong floor reading room with windows overlooking the back yard and books for each of us to enjoy reading with our evening glass of wine - in glass wineglasses borrowed from the dining room's built-in china cabinets - at Jeannie's insistence! Our three-course gourmet breakfast in the gorgeous formal dining room was perfectly seasoned cheese & vegetable quiche, keilbassa, fruit-yogurt & granola, and generous slice of moist lemon pound cake with vanilla icing was just one of Jeannie's specialties. Each room in the house is beautifully furnished, spotlessly clean, and charmingly historic from the original pine floors to the 1900's chandeliers to the pristine wide, white wood trim, yet is refreshingly modern with a small fridge, updated bathrooms, and comfortable beds & pillows. Our top floor suite has windows we could open that let in fresh breezes all night! Truly a lovely experience and a B&B our family highly recommends!
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Response from bbjeanne, Owner at Old Waterstreet Inn
Responded Nov 6, 2018
Thank you very much for your very kind and complimentary words. It makes an Innkeeper feel very satisfied when the guests leave on such a happy note. It was a pleasure to chat with you and to have you as our guests. And thanks for taking the time to write this review☺️ We hope to see you again....
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United StatesVirginiaWinchester
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Frequently Asked Questions about Old Waterstreet Inn
Which popular attractions are close to Old Waterstreet Inn?
Nearby attractions include Handley Regional Library (0.2 miles), Shenandoah Valley Discovery Museum (0.2 miles), and Shenandoah Valley Civil War Museum (0.2 miles).
What are some of the property amenities at Old Waterstreet Inn?
Some of the more popular amenities offered include free wifi, free breakfast, and free parking.
What food & drink options are available at Old Waterstreet Inn?
Guests can enjoy free breakfast during their stay.
Is parking available at Old Waterstreet Inn?
Yes, free parking is available to guests.
What are some restaurants close to Old Waterstreet Inn?
Conveniently located restaurants include Violino Ristorante Italiano, Roma Old Town Wood-Fired Pizzeria, and Thai Winchester.
Is Old Waterstreet Inn located near the city center?
Yes, it is 0.3 miles away from the center of Winchester.
Are there any historical sites close to Old Waterstreet Inn?
Many travelers enjoy visiting Patsy Cline Historic House (0.5 miles), Abram's Delight (1.2 miles), and Star Fort (1.6 miles).