Old Waterstreet Inn

217 West Boscawen Street, Winchester, Virginia 22603
Innkeeper(s): Jeannie Faith

Mr. Moore's Study

From $140.00 / night

This is a lovely room that was added in the 1940s as a study by the Virginia senator and Speaker of the House E. Blackburn Moore.

  • beautiful woodwork
  • queen wrought iron bed
  • built-in corner shelves
  • mantle
  • bath with a tiled shower and pedestal sink
  • smallest room
  • seating for two
  • only first floor room

Rate - $140 including breakfast


The Braeburn Room

From $140.00 / night

This is a romantic (but not frilly!) room with soothing sage walls and lavender accents.

  • queen carved oak bed
  • mantle
  • individual heat control
  • bath with a tiled shower
  • medium sized, second floor room

Rate - $140 including breakfast


The Winesap Room

$150.00 / $165.00 night

This large room is warmed by rose walls and sage accents, and the triple bowed window brings in lots of light.

  • queen mission style panel bed
  • desk
  • wood burning fireplace (seasonal)
  • built-in bookshelves
  • shuttered windows
  • individual heat control
  • bath has a tiled shower
  • vanity table
  • heated tile floors
  • second floor room

Rate - $150 mid march - mid November / $165 Winter, includes breakfast


The Cortland Room

$150.00 / $160.00 night

This large room is distinctly decorated with midnight blue walls, white woodwork, and a touch of green accents.

  • queen sleigh bed
  • wood burning fireplace (seasonal)
  • slant top dresser/desk
  • reclining wingback chair
  • cotton robes
  • individual heat control
  • only room where you can kick back on a private porch
  • view over the back yard from rocking chairs
  • adjacent private bath is just outside room
  • tiled tub/shower and marble floor
  • second floor room that faces the back yard

Rate: $150 mid March - mid November / $160 mid November - mid March , includes breakfast


The Cottage Suite

From $160.00 / night

Enter through French doors and climb the steps to a charming, very private attic suite.

  • only room with a separate sitting room
  • queen sofa bed that can accommodate a third person
  • cottage style room
  • built-in cupboards and drawers
  • individually controlled heat and central air
  • queen metal bed
  • the only room with a television and a selection of DVDs
  • bath with a tiled tub/shower and a pedestal sink
  • only room on the 3rd floor (attic)

Rate - $160 including breakfast

DVD Player
  • Amenities

    • Full breakfast with hot entree served daily.
    • Soft drinks, tea, and light holdover snacks always available
    • Wireless Internet.
    • Off-street private parking
    • Two public rooms, a terrace garden and yard with flowerbeds.
    • Fresh flowers and bedside chocolates in all rooms
    • Comfortable seating for two in each room
    • Wood burning fireplaces in 2 rooms (Cortland and Winesap)
    • Woodburning fireplace in living room
    • Choice of down or firm pillows, down comforters in winter.
    • Alarm clocks and hairdryers
    • Television in the Cottage Suite (only)
    • Good selection of short reading and browsing books
    • Special packages can be arranged to suit your needs
  • Guest Information

    We are open all year, except Thanksgiving and Dec. 23-26.

    Rates include a full breakfast, 24-hour soft drinks or tea, and on weekends a wine and cheese hour. Breakfast is served from 8:30 - 9:30 on weekdays, and 8:30 to 10:00 on Saturday and Sunday, with coffee available earlier.

    On a few holidays and special event weekends we have a 2 night minimum, as well as all weekends in October. In winter the Winesap room has a 2 night minimum on weekends

    Check in is from 3:00 p.m. - 6:30 p.m. Late check-ins are fine but need to be prearranged. Guests are welcome to arrive early and park in our private lot. Check-out is 11:00 a.m.

    We are a non-smoking inn. Guests can smoke outside in the yard or on the terrace. If a guest smokes inside the house, there will be a minimum $150 cleaning fee.

    A MasterCard or visa is required to reserve the room.

    Children over 13 can be accommodated in the Cottage Suite.

    We cannot accommodate pets.

    Cancellation policy: Due to our small size, cancellations are very costly to us. For a 1 night stay (1 room), if you cancel in 8 days out or more, there is no penalty fee. For multi-night stays or multi-room stays, you need to cancel 14 days out or more. If you cancel within these periods, you will be charged the full amount unless we are able to rebook the room. Cancellation fees apply regardless of the reason and changes are treated the same as cancellations.

    we discount the 3rd night or more by 15%

    Gift certificates available