Old Waterstreet Inn

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

    Old Waterstreet Inn...in the Heart of Winchester's Historic District

    Indulge yourself with a stay at the Old Waterstreet Inn, where you can unwind in an atmosphere that is easy going and relaxed, yet sophisticated. We are located in the historic district, within easy walking distance of many shops, restaurants and nightlife.

    Old Waterstreet Inn, living room Recommended by Frommers, Fodors,  featured in Washingtonian magazine February 2008, very highly rated on Tripadvisor.

    In the words of one of our guests, the Old Waterstreet Inn is "outstanding in every way." The federal style brick home, which is designated a Winchester Historic Building, was built in 1840 - 1890. 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.

    The inn has two public rooms, the living room and a second floor sunroom, where guests can relax, socialize, listen to music, read, watch the fire, or plan dinner by looking through our local restaurant menus. We have a good selection of interesting reading that includes short story collections, short nonfiction, travel books and magazines, and "browsing" books. In nice weather, guests can relax on the terrace garden or in the yard with flowerbeds.

    We invite you to come and fall in love with our Inn - and with each other all over again.

  • Insider's Info

    Travelers are always looking for memorable and relaxing experiences. Let’s discover more through the words of our innkeepers. Many thanks to Jeannie Faith for sharing her own secrets with BBOnline.com!
    Why do most travelers stay at your inn?

    We are located in Old Town.

    What are you best known for? What makes your inn unique? What do you love most about your inn?

    We are best known for a relaxed atmosphere, attentive hosts, our mixed style, and attention to detail.

    If someone has never been to your city, what is the #1 reason to come visit?

    Old Town charm, dining, and shopping

    What’s the best compliment you have ever received about the inn?

    "Outstanding in every way"

    What’s the best kept secret about the area?

    No Comment

    If a traveler is staying at your inn for 4 nights, what should he/she do in the area?

    Explore Old Town architecture, shops, restaurants, and galleries, Historic homes, museums, antiquing in the area, wineries, see a show at Winchester Little Theatre or Shenandoah University, nearby skyline drive and nearby hiking.

    Is there anything within walking distance of your inn?

    Old Town shops and restaurants and galleries and nightlife, Museum of Shenandoah Valley, Jackson's Headquarters Museum, Civil War Museum, George Washington's Office museum

    What is your favorite restaurant/food in the area?

    Our favorite restaurants are One Block west, Violino, Chopstick cafe, and La Nicoise Cafe.

    Any good area guides/websites that travelers could reference?

    www.visitwinchestervirginia.com/ and www.virginiawine.org

    How many rooms does your inn have?

    We have 5 rooms.

    Do you accept pets?

    We do not accept pets.

  • Breakfast and Snacks

    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 pecan pancakes, amaretto French toast, quiche or other specialty egg dishes.

    In our pantry, guests can always find complimentary sodas and juice, light holdover snacks, and tea or seasonal drinks.

  • Things to Do in Winchester and the Area

    There are plenty of activities and sites to see in the Winchester area. For a more detailed list, please visit the "things to do" page of our website.

    • Old Town
    • Dining
    • Theatre and concerts
    • Historic Interest and Museums in Winchester and nearby
    • Annual Events
    • Shopping
    • Antiques
    • Outdoor and sports in Winchester and the area
    • Wineries

    Please also check the following website for further information: www.visitwinchesterva.com

  • Guest Comments

    Old Waterstreet Inn, staircase "Absolutely lovely accomodations and fabulous hosts! We appreciate all your special touches and your terrific hospitality. We'll definitely plan a return visit."

    - Bayonne, NJ

    “Our hosts could not have been more warm, gracious, and professional. They know exactly when to approach and when to unobtrusively withdraw. They know the best restaurants to recommend and the breakfasts are delicious. Not least, the rooms are all individualized and impeccably appointed. The weekend was a tonic for us.” - Washington, D.C.

    “A charming period inn and gracious hosts, all in a beautiful old city. What more could we a

    “Wonderfully comfortable.” - Westhampton. NJ

    “We travel and stay at a lot of b&bs – this is one of the best. Jeanne and Erik have paid great attention to every detail to make our stay memorable.” - Falls Church, VA