Historic Bed & Breakfast Inn Old Town Winchester Virginia

Nancy Shepherd House Inn B&B in Old Town Winchester Virginia

For availability, text or call 540-247-5073

Rooms: $150.00 plus tax for first night.

For a stay of more than one night, rooms are $100.00 plus tax per night after the first night.

Looking for interesting historic places to stay right in Old Town Winchester Virginia?

If you are searching for a great historic lodging experience in the Shenandoah Valley, or a nice place have a small wedding or elopement in Old Town Winchester Virginia, here it is!

view of the front of the inn from Loudoun Street

Nancy Shepherd House Inn in Old Town Winchester with original colors from 1810

To inquire about the Nancy Shepherd House Inn in Old Town Winchester Virginia, call or text 540-247-5073

Historic Bed and Breakfast in Winchester Virginia in the Shenandoah Valley

About the Nancy Shepherd House Inn…

The Nancy Shepherd House is an unusual and interesting historic inn for overnight lodging accommodations in downtown Winchester Virginia’s “Old Town” historic district. It was built in about 1772 at what was the south end of town before the revolution, now 618 South Loudoun Street, just four blocks south of the Old Town pedestrian mall. The Nancy Shepherd House Inn was formerly a Winchester Virginia tavern and inn run by Mary Cochran from 1798 until the 1840s, and then by Oscar Brown until the end of the Civil War. After the war, it was a tenement apartment building for 122 years. Its current owner bought the old inn in a state of ruin in 1987 and commenced on a 21 year restoration project to bring it back for service as an inn and bed and breakfast. When the project was completed, it became a licensed hotel and B&B, and venue for small events.

The Nancy Shepherd House Inn was built originally as a one-story log dwelling. It was enlarged in the 1790s, and was run as a small inn and tavern for lodgers in what is now Old Town Winchester, Virginia. It is now beautifully restored back to its original pre-civil war appearance and layout, with a mission of conservation of it’s early material and historic vibe. You feel like you are stepping back in time at the Nancy Shepherd House, with it’s rough original floors, and crooked walls.

Today, breakfast is no longer served at the Nancy Shepherd House since it is right downtown with great restaurant options all around within walking distance. The Nancy Shepherd House Inn is very close to Winchester’s Old Town pedestrian mall, so you can walk to the many restaurants, shops, galleries, pubs, and coffee houses.

The Nancy Shepherd House Inn is one of only three licensed options for lodging accommodations for visitors and tourists who want to stay downtown within walking distance to the center of Old Town Winchester Virginia. The other two licensed establishments for lodging in Old Town are the Fuller House Inn, and the George Washington Hotel.

All three bedrooms at the Nancy Shepherd House Inn have thick luxury queen-size memory foam mattresses on solid platform beds, for the best sleep comfort. There is no TV at the inn, but there are plenty of great books and good business WiFi for your device.

For a one-night stay, bedrooms are $150.00 plus tax for the night. 

For a stay of more than one night, Rooms are $100.00 plus tax per night after the first night.

There are no ensuite bathrooms. Bathrooms are across the hall, and are shared only if you have a group booking.

Each bedroom has a Keurig Coffee machine and a small refrigerator with freezer.

Call 540-247-5073 to book your room or rooms.

We no longer take credit cards. Rooms can be reserved by making a non-refundable payment of the entire amount by CashApp or Zelle. After payment has been made you will receive an email confirmation and it goes into our book as a non-refundable committed reservation.

East parlor of the inn showing antiques

East Parlor at the Nancy Shepherd House Inn – Photo by Aaron Riddle

West Parlor at the Nancy Shepherd House

The Nancy Shepherd House Inn (formerly a Bed and Breakfast) in Old Town Winchester VA is now a fully licensed historic hotel. It is one of few remaining early federal period inns that once lined the streets of downtown Winchester, Virginia before the Civil War.

It is anlso available for small weddings, receptions, garden parties, celebration events and overnight lodging accommodations. The Nancy Shepherd House Inn is a rare surviving example of an early Old Town Winchester inn. It is right downtown in Winchester’s historic district, with quaint shops, gourmet coffee houses, pubs, and fine restaurants all within easy walking distance. If you would like to stay right in Old Town Winchester, consider the Nancy Shepherd House Inn.

A bedroom at the inn…

Lodging couple in the east bedroom

Eloping couple in Bedroom 1 at the Nancy Shepherd House Inn – Photo by Aaron Riddle

The back garden in the Springtime…

Couple getting married in the back garden at the Nancy Shepherd House Inn – Photo by Aaron Riddle


If we book a room at the inn or the cottage, what time is check-in and check-out?

Check-in is any time after 3;00pm, and check-out is any time before 11:00 am. Since I run the place myself, please call me when you are close to arriving so that I can be sure to be at the inn when you arrive.

Do you have WiFi?

Yes, the inn and cottage provide business wifi at no extra charge.

Why did you stop serving breakfast?

Since the Nancy Shepherd House Inn and Fuller House Cottage are right downtown where all the action is, there are some really wonderful restaurants very nearby within walking distance, we decided to lower our rates by discontinuing breakfast and run the inn for lodging only. We have Keurig coffee maker in each room. Bring your own pods or use our standard breakfast blend.

What size are your beds? 

All of our beds are high-end full 14 inch memory foam queen platform beds with breathable soft covers. The Fuller House Cottage has the same memory foam bed, but in King size! You won’t find more comfortable beds in Winchester VA.

My husband is very tall. How is your shower at the Nancy Shepherd House?

The shower-for-two on the second floor of the Nancy Shepherd House is huge and since I hate bending over to take a shower, I designed a large shower for tall people. It comfortably fits two people and has two seats in it. The shower on the third floor is a standard tub and shower combo, and the third floor in general is not a good for tall people.

Is there individual climate control in each room at the Nancy Shepherd House?

No, but the whole building has central heat and air conditioning. For the forced air system, you can close off the vents if you don’t want air flow. During the cold season, each bedroom comes with a good space heater as well.

Do you have a fridge we can put our bottled drinks and left over food in?

Each bedroom has a refrigerator with freezer for your food and drinks. The Fuller House Cottage has its own fantastic kitchenette on the first floor with a full size fridge. Too many guests were destroying microwave ovens, so we no longer provide them.

Your inn is extremely old and crooked, has old rough unfinished floors, tattered rugs, and has places where we bumped our heads. We thought it would be nice and new with smooth floors and television, like a motel.

Yes, this building is a *real* 18th century building and is not for everyone. If you “just need a room” because all the motels are sold out, this old historic inn Is probably not right for you. For example, do you find the following photos of the original pre-revolutionary floor and the tattered antique rug unpleasant or disturbing? If so, you will certainly not like this old inn.

Close-up photo of old rough and worn floor boards

Original pre-revolutionary floor at the Nancy Shepherd House

Old rug at the inn

Antique rug in the front parlor at the Nancy Shepherd House

view of the front of the inn from the street

Nancy Shepherd House Inn B&B Old Town Winchester Virginia

Another great and fantastic historic place to stay in Old Town Winchester is the Fuller House, which is fully licensed with rooms for lodging, plus a romantic getaway cottage in the garden.

Historic lodging in Virginia

Honeymoon Destination Lodging and Elopement Package in Old Town Winchester Virginia for only $250.00 plus tax.

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