Photo by Tina McClelland

Find hotels in Old Town Winchester, Winchester

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Check prices for these dates

Tonight
Jan 9 - Jan 10
Tomorrow
Jan 10 - Jan 11
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Old Town Winchester hotels

Bar (on property)
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1,004 reviews)
"Great hotel!"
United States
CHARLES
The price is ₩184,092
₩208,575 total
includes taxes & fees
Jan 18 - Jan 19
The George Washington Hotel, A Wyndham Grand Hotel
Restaurant
The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino
3.0 star property
30 km from Old Town Winchester
8.6 out of 10, Excellent, (531 reviews)
"Friendly staff, comfortable bed, convenient location "
United States
Kourtney
The price is ₩173,916
₩209,282 total
includes taxes & fees
Feb 9 - Feb 10
The Inn at Charles Town - Hollywood Casino
2 bars/lounges, sports bar
Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town
2.0 star property
29.7 km from Old Town Winchester
8.6 out of 10, Excellent, (1,005 reviews)
"Certainly will stay again "
United States
philip
The price is ₩92,649
₩104,694 total
includes taxes & fees
Jan 26 - Jan 27
Rodeway Inn & Suites Charles Town
Lobby
Days Inn by Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry
2.0 star property
29.6 km from Old Town Winchester
8.0 out of 10, Very Good, (1,003 reviews)
"Nice place to stay"
United States
Cynthia
The price is ₩96,749
₩109,327 total
includes taxes & fees
Jan 11 - Jan 12
Days Inn by Wyndham Charles Town/Harpers Ferry
Room, 1 King Bed, Non Smoking | Premium bedding, pillowtop beds, blackout drapes, iron/ironing board
Travelodge By Wyndham Charles Town/Harpers Ferry

Travelodge By Wyndham Charles Town/Harpers Ferry

Travelodge By Wyndham Charles Town/Harpers Ferry
2.0 star property
29.5 km from Old Town Winchester
6.8 out of 10, (265 reviews)
"Room was very clean and quiet!"
United States
Mary ann
The price is ₩92,401
₩104,413 total
includes taxes & fees
Jan 11 - Jan 12
Travelodge By Wyndham Charles Town/Harpers Ferry
Front of property
The Carriage Inn B&B

The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
29.3 km from Old Town Winchester
9.6 out of 10, Exceptional, (440 reviews)
"Excellent accommodations and breakfast. "
United States
William
The price is ₩188,380
₩212,887 total
includes taxes & fees
Feb 9 - Feb 10
The Carriage Inn B&B
Garden
L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
14.1 km from Old Town Winchester
9.6 out of 10, Exceptional, (175 reviews)
"This B&B has been by far the loveliest, friendliest, cleanest with staff so eager to please. The rural area was so peaceful and relaxing with views of black angus in the fields. Winchester close with quaint shops. The food at the Inn was excellent. "
United States
DONNA
The price is ₩331,917
₩366,104 total
includes taxes & fees
Jan 13 - Jan 14
L'Auberge Provencale Inn & Restaurant
Restaurant
Hampton Inn Martinsburg South-Inwood

Hampton Inn Martinsburg South-Inwood

Hampton Inn Martinsburg South-Inwood
2.5 star property
22.3 km from Old Town Winchester
9.2 out of 10, Wonderful, (648 reviews)
"Very clean, friendly staff would definitely stay there again. "
United States
John
The price is ₩124,075
₩138,965 total
includes taxes & fees
Feb 1 - Feb 2
Hampton Inn Martinsburg South-Inwood
Reception
TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester

TownePlace Suites by Marriott Winchester
3.0 star property
3 km from Old Town Winchester
8.8 out of 10, Excellent, (485 reviews)
"Nice place to stay. Great staff and breakfast."
United States
Stormy
The price is ₩163,857
₩178,277 total
includes taxes & fees
Jan 21 - Jan 22
TownePlace Suites by Marriott Winchester
Exterior
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
5.3 km from Old Town Winchester
9.4 out of 10, Exceptional, (796 reviews)
"Great stay!"
United States
Rene
The price is ₩155,675
₩169,374 total
includes taxes & fees
Jan 18 - Jan 19
SpringHill Suites by Marriott Winchester
Pool
APM Inn & Suites

APM Inn & Suites

APM Inn & Suites
2.0 star property
2.3 km from Old Town Winchester
6.6 out of 10, (353 reviews)
"Room was quite nice for the price, and check in lady was very nice "
United States
Glen
The price is ₩78,268
₩88,678 total
includes taxes & fees
Jan 10 - Jan 11
APM Inn & Suites
Winery
Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park

Baymont by Wyndham Front Royal Near Shenandoah National Park
2.5 star property
29.8 km from Old Town Winchester
6.4 out of 10, (925 reviews)
"Staff was very kind! Had a nice time!"
United States
Rio Ashley
The price is ₩80,080
₩89,130 total
includes taxes & fees
Jan 18 - Jan 19
Baymont by Wyndham Front Royal Near Shenandoah National Park
Lobby
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
4.1 km from Old Town Winchester
9.2 out of 10, Wonderful, (1,424 reviews)
"Clean room and bathroom, friendly staff, helpful."
United States
Thomas
The price is ₩115,121
₩125,252 total
includes taxes & fees
Feb 8 - Feb 9
Microtel Inn & Suites by Wyndham Winchester
Suite, 1 Bedroom | In-room safe, desk, laptop workspace, blackout drapes
Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG

Candlewood Suites Winchester by IHG
2.5 star property
3.1 km from Old Town Winchester
8.8 out of 10, Excellent, (549 reviews)
"The room was just the right temp, check in with my service dog was the most professional I’ve experienced! "
United States
Shenandoah
The price is ₩127,912
₩139,168 total
includes taxes & fees
Jan 13 - Jan 14
Candlewood Suites Winchester by IHG
Exterior
Quality Inn Winchester

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
4.3 km from Old Town Winchester
9.2 out of 10, Wonderful, (1,001 reviews)
"Great stay, as usual"
United States
Mary
The price is ₩122,316
₩133,081 total
includes taxes & fees
Jan 16 - Jan 17
Quality Inn Winchester
Front of property
Hillbrook Inn

Hillbrook Inn

Hillbrook Inn
4.0 star property
21.7 km from Old Town Winchester
8.6 out of 10, Excellent, (671 reviews)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
United States
Nataliya
The price is ₩230,458
₩294,350 total
includes taxes & fees
Jan 11 - Jan 12
Hillbrook Inn
Free daily on-the-go breakfast
Days Inn by Wyndham Winchester

Days Inn by Wyndham Winchester

Days Inn by Wyndham Winchester
2.0 star property
4.2 km from Old Town Winchester
6.6 out of 10, (486 reviews)
"Very comfortable stay"
United States
Jose David
The price is ₩91,574
₩99,641 total
includes taxes & fees
Feb 1 - Feb 2
Days Inn by Wyndham Winchester
Restaurant
Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
2.1 km from Old Town Winchester
9.2 out of 10, Wonderful, (854 reviews)
"Clean room very nice staff"
United States
JEROME J
The price is ₩153,757
₩174,206 total
includes taxes & fees
Jan 16 - Jan 17
Hampton Inn Winchester N/Conference Center, VA
Lobby
Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park
2.0 star property
30.4 km from Old Town Winchester
7.6 out of 10, Good, (1,001 reviews)
"Good condition "
United States
Phillip
The price is ₩81,108
₩90,273 total
includes taxes & fees
Jan 13 - Jan 14
Super 8 by Wyndham Front Royal Near Shenandoah National Park
Snack bar
TRU By Hilton Winchester

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
4.4 km from Old Town Winchester
9.0 out of 10, Wonderful, (784 reviews)
"Clean room, good breakfast, easy check in/out."
United States
Joseph
The price is ₩108,115
₩117,628 total
includes taxes & fees
Jan 26 - Jan 27
TRU By Hilton Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

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

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

Top Old Town Winchester Hotel Reviews

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent
"Service was exceptional. It’s a small hotel, but was clean and great service. "
Danah 6-night trip
Posted 3 days ago
Microtel Inn & Suites by Wyndham Winchester

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 Expedia customer reviews, The George Washington Hotel, A Wyndham Grand Hotel is the highest ranked property 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 11 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 Handley Regional Library are some other stops to visit in the neighborhood. A few places to visit in the area around Old Town Winchester include George Washington's Office, 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.