A grand old home in the historic district of Winchester


Winchester is a lovely small city with an historic center. Old Waterstreet Inn is located in Old Town, just 2 blocks from the charming walking mall, where you'll find interesting shops, restaurants, galleries, and nightlife. It's the perfect place for a romantic getaway, or a relaxing break from the big city, and it's a great base for area attractions, history, events, or business.

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 - 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 ambience.

"We travel and stay at a lot of b&bs ' this is
one of the best. Jeannie and Erik have paid
great attention to every detail and made our
stay memorable."

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. Bread, bagels, or muffins are served with egg dishes.


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

The inn has two public rooms, the living room and a second floor sunroom, where guests can relax, socialize, listen to music, read, 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. On winter evenings, guests can enjoy the glowing fireplace in the living room, and in warm months, guests can relax on our terrace garden, or in the yard with its colorful flowerbeds.

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.

In addition to our specials that change throughout the year, we'll be happy to tailor special packages to your needs. For the business traveler, we offer extended stay rates, wireless internet access from all rooms and the terrace, and copying is available.