Top Old Town Winchester Hotels

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Where to stay in Old Town Winchester

Find the best Old Town Winchester areas and neighborhoods for the activities you enjoy most.

Winchester Historic District

Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.

See properties

Top Old Town Winchester Hotel Reviews

TRU By Hilton Winchester

10/10 Excellent

"Parking was good enough. Breakfast was just ok. The room was excellent for the price. "

Ramada by Wyndham Strasburg/Shenandoah Valley

6/10 Okay

"The room was booked through Expedia 3 months ago. I requested a quiet room(not right by ice maker, elevator, etc) but refused by the receptionist. The reason is how the room was booked. Hey, I paid more than the hotel's web site pricing as I checked after getting into the room. There are laundry room, breakfast room, business center on right side of the hallway and guest rooms on left. Mine is the last one with the hallway leading to hotel restaurant through another door. Few times I felt and heard the vibration of washer high speed spin dry. I dreaded; luckily no guests did laundry after 11pm. I'm alerted that some hotel has differential treatment to guest from third party booking even like this one, even though I paid early at a higher out of pocket price - and hotel doesn't reveal such rule on Expedia. I don't know Expedia realizes such behavior by certain hotel. I certainly don't accept being a lower class guest while paying more. Btw, this hotel has a post stating it's privately run under a license from Wyndham. No wonder it's not up to the Wyndham 's standards"

Travelodge by Wyndham Winchester

2/10 Terrible

"The handle to control the water in the bathroom was almost completely off so you either had really cold or really hot water. There was individuals hanging outside of the entrance to the hotel acting very weird as if on drugs. We was placed on the 3rd floor and it smelled completely of smoke because long term individuals was allowed to smoke in the stairwell. The TV had a mind of its own and would sometimes work. We was only given two towels and two washcloths for a family sized group. There was groups of people loitering in the lobby making comments as we walked by to go to our room after visiting attractions in the area. "

Frequently asked questions

What is Old Town Winchester like?

Old Town Winchester is a historic neighborhood known for its array of dining options. Are you looking for Old Town Winchester travel tips? Be sure to check out Bright Box Theater and Shenandoah Valley Discovery Museum while you're in the neighborhood.

Where is the best place to stay in Old Town Winchester?

Based on our traveler data, The George Washington Hotel, A Wyndham Grand Hotel is one of the top choices for your stay in Old Town Winchester. This hotel offers a full-service spa and 2 restaurants.

How many hotels can I expect to find in the Old Town Winchester area?

With 13 Expedia hotels and other accommodations in Old Town Winchester to choose from, this is a good starting point for exploring the greater Winchester area.

If I need to cancel my hotel reservation in Old Town Winchester, will I receive a refund?

Yes, most hotel bookings are fully refundable if cancelled prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If you booked a non-refundable reservation, it may still be possible to cancel it and get a refund within 24 hours of your booking. Plug in your dates, click on "Search", then filter by "fully refundable" to get top deals in Old Town Winchester.

Where can I learn more about changing or cancelling my trip to Old Town Winchester?

For additional details about rescheduling or cancelling your trip to Old Town Winchester, head over to our customer service page.

What is there to do around this Winchester neighborhood?

Sights like Bright Box Theater and Old Court House Civil War Museum can be part of your cultural tour of Old Town Winchester. Shenandoah Valley Discovery Museum and George Washington's Office are some other stops to visit in the neighborhood. A few places to visit in the area around Old Town Winchester include Handley Regional Library, Mt Hebron Cemetery, and Winchester Little Theater. When you're sightseeing in Winchester, Stonewall Jackson's Headquarters and Patsy Cline Historic House are also worth a stop.

Explore a world of travel with Expedia

Book Hotels in Old Town Winchester on Expedia.com

Find hotels in Old Town Winchester, Winchester

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Our top choices for Old Town Winchester hotels

The George Washington Hotel, A Wyndham Grand Hotel

Super 8 by Wyndham Front Royal Near Shenandoah National Park

L'Auberge Provencale Inn & Restaurant

Spark by Hilton Winchester

Travelodge By Wyndham Charles Town/Harpers Ferry

Hillbrook Inn

Hampton Inn Front Royal

Relax Inn Motel

The Inn at Charles Town - Hollywood Casino

Days Inn by Wyndham Charles Town/Harpers Ferry

La Quinta Inn & Suites by Wyndham Winchester

Wayside Inn

Comfort Inn & Suites Winchester

Motel 6 Front Royal, VA

APM Inn & Suites

The Carriage Inn B&B

Twi-Lite Inn

TownePlace Suites by Marriott Winchester

Hampton Inn Winchester N/Conference Center, VA

Courtyard by Marriott Winchester