Old Waterstreet Inn

Manager: jeanne faith
Address: 217 W. Boscawen St. Winchester, Virginia 22601
Phone: 540-665-6777
Rates: 130 - 150
Rooms: 5
Bathrooms: 5
Check In/Out: 3:00-6:00 / 11:00
Extra Person: $45
Check Availability

Old Waterstreet Inn is located in Old Town, just two blocks from the pedestrian street.  Come and unwind in an atmosphere that is easy going yet sophisticated. Our Inn, which is designated a Winchester Historic Building, was built in 1840. Architectural details enhance the elegance of the inn.    Your hosts have decorated the inn in an eclectic mix of styles, and of old and new, which creates a charming casual ambiance.

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.  On winter weekends, guests can enjoy sitting by the fire 8n the living room before heading out to dinner.  

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.


Stay longer and save

stay theee nights in the same room and take 15  % off the third night or more.   

Price: $120-140
Valid 06/27/2018 thru 06/27/2020

Seniors Special

For seniors 62 and over, stay any weeknight and take $10 off per night. Stay any two nights on a weekend, and take $10 off per night.   Excludes holidays , event weeekends, and all weekends in October.   Must book at least 7 days out and must ask for this special when booking 

Price: $125-150
Valid 06/27/2019 thru 10/02/2019

Bed , no breakfast!

Without breakfast take $15 off per night on any room.   This must be booked this way, it cannot be changed at the last minute.  

Valid 07/05/2019 thru 12/15/2019

Wine and cheese Special

You will be  welcomed in your room at check in to a bottle of red or white wine, and two types of cheese and crackers.  Add $25 to the room rate, must order at least 3 days ahead.   

Valid 08/03/2019 thru 10/31/2019

Last minute special Aug 23 and 24

Due to a cancellation, we have Mr. Moore’s Study available Aug 23 and 24.   Stay two nights and take $10 off per night, for a rate of $120.   Please call before 5:00 Friday to take advantage of this special    

Valid 08/23/2019 thru 08/24/2019

Room Amenities:

  • AC, Central
  • Bath, Private Ensuite
  • Bed, Queen
  • Hair Dryer
  • Iron/Ironing Board Available
  • Bath, Private Hallway
  • Wi-Fi

Inn Amenities:

  • Common Fireplace
  • Complimentary Beverages
  • Complimentary Snacks
  • Internet Access
  • Off Street Parking
  • Outdoor Guest Areas
  • WiFi Throughout
  • First Floor Rooms

Area Activities:

  • Antiquing
  • Biking
  • Breweries
  • Farmers Markets
  • Fine Dining
  • Hiking
  • Historic Sites
  • Horseback Riding
  • National & State Parks
  • Theater
  • Unique Shopping
  • Wineries
  • Fishing
  • Golf

Geographic Settings:

  • City

Well Suited For:

  • Honeymoons
  • LGBT Friendly
  • Romantic Escape
  • Elopements

Food Services:

  • Breakfast, Full
  • Coffee/Tea available 24-hours
  • Meal Options, Vegetarian

Inn Policies:

  • Alcoholic Beverages Permitted
  • Cash Accepted
  • Checks Accepted
  • Children 12+ Permitted
  • Credit Cards Accepted
  • Smoke Free Property
  • Smoking Outside Only

Minimum Stay Required:

  • Holidays
  • Special Events


  • Virginia Green