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Winchester, Virginia Bed and Breakfasts
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  • Old Waterstreet Inn
  • Dining Room
  • Inn entrance foyer
  • Terrace Garden
  • Winesap Room
  • Braeburn Room
  • Cortland Room
  • Old Waterstreet in Spring
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Old Waterstreet Inn

Your host(s):
Jeannie Faith and Erik Erdal
Web Site:
217 W. Boscowan St.
Winchester, Virginia 22601
Guest Rooms:
5Bathrooms: 5
$130 - $160
Check In/Out:
3-6:30 PM - 11 AM
Extra Person Fee:
Social Media:
Gay/Lesbian Friendly:

Old Waterstreet Inn

At Old Waterstreet Inn, you can unwind in an atmosphere that is easy going yet sophisticated.

The federal style brick home, which is designated a Winchester Historic Building, was built in 1840.

Architectural details enhance the elegance of the inn, with its high ceilings, classic archways and moldings, fireplaces, lovely staircase, and built-in corner cabinets.

Your hosts have decorated the inn in an eclectic mix of styles, and of old and new, which creates a charming casual ambiance.

"Outstanding in every way."
Featured in Washingtonian magazine Feb. 2008, recommended by Frommers and Fodors, featured in Blue Ridge Country Dec. 2007
User rating of 4.5 out of 5 on Tripadvisor

A full breakfast is served in our gracious dining room. After fresh fruit and/or yogurt and granola with a choice of mix-ins, your hot entree might be Apple Pancakes, Asparagus Smoked Gouda Quiche, Almond Amaretto French Toast, or other specialty egg or sweet dishes.

Guests can always find complimentary sodas and juice, light snacks, and tea or seasonal drinks in our pantry.
The inn is spacious, with two public rooms, the living room and a second floor sunroom.   Guests can relax, socialize, listen to music, read from our interesting collection of books and magazines, or review menus for one of our excellent Old Town restaurants.

In nice weather, guests can relax on the terrace garden or on the adirondack chairs in the yard.

Each of our 5 rooms (4 rooms and 1 suite) has its own distinct character to suit different tastes. For time alone or quiet relaxation, guest rooms all have comfortable seating for two.  Fresh flowers always brighten your room.

For the business traveler, we offer wireless internet access, dry cleaning just across the street, and copying is available.  

View Our Reviews

Packages & Specials Select Dates Midweek Special - $130-$145
Monday Nov.30 through Thursday Dec. 3rd Only - Stay two nights and take $15 off per night on Cottage Suite, or $10 off per night on all other rooms . Must book by 6 pm the day before, no exceptions, please ask for this special when booking

Seniors Special - 130-155
Through Dec. 19 - For "seniors" aged 62 and older - book for any weekday, at least 8 days in advance, and take $10 off of a one night stay, or $15 off per night on a two night stay. Must ask for this special when booking, cannot be combined with other offers

Multi Night Stays - $119-$136
Stay 3 nights or more in the same room and get 15% off the third (or more) nights. Cannot be combined with other offers.

Cancellation Policy

Cancellation policy: Due to our small size, cancellations can be extremely costly for us. Therefore, for a 1 night stay: if you cancel 8 days or more before, there is no penalty. If you cancel in 7 days or less, you will be charged the full amount. For multi night or multi room stays: you must cancel 14 days out, penalty is as above noted.  If we are able to rebook the room for the nights you reserved you will not be charged. Changes are treated the same as cancellations.

Area Activities

  • Antiquing
  • Biking
  • Canoeing
  • Fishing
  • Galleries
  • Golf
  • Hiking
  • Historic Sites
  • Horseback Riding
  • Museums
  • National/State Parks
  • Outlet Malls
  • Theater
  • Unique Shopping
  • Wineries

Food Service

  • Accommodates Special Diets
  • Coffee/Tea available 24-hours
  • Early Morning Coffee/Tea
  • Full Breakfast

Geographic Setting

  • Small Town

Inn Amenities

  • Common Fireplace
  • Comp. Beverages
  • Comp. Light Refreshments
  • Copy Service
  • First Floor Rooms
  • Gardens
  • Green Friendly
  • Internet Access
  • Off Street Parking
  • Outdoor Guest Areas
  • WiFi Throughout

Inn Policies

  • Alcoholic Beverages Permitted
  • Cash Accepted
  • Checks Accepted
  • Children 12+ Permitted
  • Credit Cards Accepted
  • Pets Not Permitted
  • Smoking Outside Only

Minimum Stay Required

  • Holidays
  • Special Events

Room Amenities

  • AC/Central
  • Fireplace/Decorative
  • Fireplace/Wood Burning
  • Hair Dryer
  • Iron/Ironing Board Avail.
  • Private Bath
  • Private Deck
  • Queen Bed
  • Shower
  • Wi-Fi

Well Suited For

  • Business Travel
  • Elopements
  • Gay Friendly
  • Honeymoons
  • Romantic Escape
  • Single Traveler
  • Vacation Getaway