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Our top choices for Old Town Winchester hotels

2 restaurants, breakfast, lunch, dinner served; American cuisine
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, (1013)
"Great hotel!"
United States
CHARLES
The price is ￥19,754
￥22,382 total
includes taxes & fees
Jan 7 - Jan 8, 2026
The George Washington Hotel, A Wyndham Grand Hotel
Bar (on property)
DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
21.9 km from Old Town Winchester
9.0 out of 10, Wonderful, (1003)
"Friendly staff, nice clean room, hotel restaurant was delicious. "
United States
Dorothy
The price is ￥15,220
￥16,787 total
includes taxes & fees
Jan 18 - Jan 19, 2026
DoubleTree by Hilton Front Royal Blue Ridge Shadows
Lobby
Hampton Inn Front Royal

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
25 km from Old Town Winchester
9.0 out of 10, Wonderful, (1005)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is ￥17,777
￥19,785 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Hampton Inn Front Royal
Courtyard
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)
"Excellent accommodations and breakfast. "
United States
William
The price is ￥24,177
￥27,320 total
includes taxes & fees
Jan 26 - Jan 27, 2026
The Carriage Inn B&B
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, (530)
"Friendly staff, comfortable bed, convenient location "
United States
Kourtney
The price is ￥18,154
￥21,892 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Inn at Charles Town - Hollywood Casino
Property amenity
TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal
3.0 star property
24.4 km from Old Town Winchester
9.6 out of 10, Exceptional, (558)
"Excellent staff, clean rooms, convenient location right next to grocery stores and restaurants. "
United States
Carla
The price is ￥18,404
￥20,611 total
includes taxes & fees
Jan 4 - Jan 5, 2026
TownePlace Suites by Marriott Front Royal
Exterior
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
2.9 km from Old Town Winchester
9.2 out of 10, Wonderful, (2240)
"Staff is very pleasant and personable. "
United States
Julie
The price is ￥15,410
￥16,766 total
includes taxes & fees
Jan 4 - Jan 5, 2026
La Quinta Inn & Suites by Wyndham Winchester
Terrace/patio
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)
"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 ￥35,003
￥38,608 total
includes taxes & fees
Jan 5 - Jan 6, 2026
L'Auberge Provencale Inn & Restaurant
Pillowtop beds, desk, laptop workspace, blackout drapes
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, (789)
"Great staff, very clean room with a good breakfast "
United States
Jim
The price is ￥16,704
￥18,174 total
includes taxes & fees
Jan 18 - Jan 19, 2026
SpringHill Suites by Marriott Winchester
Indoor pool
Hilton Garden Inn Winchester

Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
2.1 km from Old Town Winchester
8.8 out of 10, Excellent, (514)
"Great hotel"
United States
DONNA D
The price is ￥15,733
￥17,825 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Hilton Garden Inn Winchester
Exterior
Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
2.5 star property
2.9 km from Old Town Winchester
9.0 out of 10, Wonderful, (807)
"We stay here a lot and it is always consistently clean and service is great. "
United States
Kim
The price is ￥14,451
￥15,723 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Fairfield Inn & Suites by Marriott Winchester
Restaurant
Courtyard by Marriott Winchester

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
3.1 km from Old Town Winchester
9.0 out of 10, Wonderful, (923)
"Easy check in, friendly staff, clean and quiet room. Location convenient to store."
United States
Brenda
The price is ￥16,689
￥18,157 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Courtyard by Marriott Winchester
Snack bar
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, (852)
"The room was clean, and the breakfast was plentiful. The staff was very friendly and helpful. This was the quietest stay I've had on my trips to Wincheater."
United States
Jay
The price is ￥16,499
￥18,692 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Hampton Inn Winchester N/Conference Center, VA
Property amenity
Hillbrook Inn

Hillbrook Inn

Hillbrook Inn
4.0 star property
21.7 km from Old Town Winchester
8.6 out of 10, Excellent, (671)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
United States
Nataliya
The price is ￥23,560
￥30,285 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hillbrook Inn
Exterior
Twi-Lite Inn

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
27.8 km from Old Town Winchester
8.2 out of 10, Very Good, (542)
"Clean, comfortable room. Staff was nice and I really enjoyed my stay. Motel was in a high traffic area, but still a quiet stay"
United States
Daniel
The price is ￥9,670
￥10,763 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Twi-Lite Inn
Free buffet breakfast
Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
12.4 km from Old Town Winchester
8.2 out of 10, Very Good, (808)
"Clean room, nice staff, simple but good breakfast, fresh ground coffee machine was really nice. "
United States
Rose
The price is ￥11,542
￥12,558 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Holiday Inn Express Winchester South-Stephens City by IHG
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)
"Room was very clean and quiet!"
United States
Mary ann
The price is ￥9,943
￥11,235 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Travelodge By Wyndham Charles Town/Harpers Ferry
Bar (on property)
Wayside Inn

Wayside Inn

Wayside Inn
3.5 star property
19.8 km from Old Town Winchester
9.2 out of 10, Wonderful, (419)
"Historic inn. "
United States
Anonymous traveler
The price is ￥11,230
￥13,944 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Wayside Inn
In-room safe, desk, iron/ironing board, bed sheets
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, (482)
"Nice place to stay. Great staff and breakfast."
United States
Stormy
The price is ￥16,704
￥18,174 total
includes taxes & fees
Jan 1 - Jan 2, 2026
TownePlace Suites by Marriott Winchester
Front of property - evening/night
Relax Inn Motel

Relax Inn Motel

Relax Inn Motel
2.0 star property
27.6 km from Old Town Winchester
8.2 out of 10, Very Good, (259)
"Clean, and nice rooms, friendly staff"
United States
James
The price is ￥10,606
￥11,804 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Relax Inn Motel
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.
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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

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA

10/10 Excellent
"The room was clean, and the breakfast was plentiful. The staff was very friendly and helpful. This was the quietest stay I've had on my trips to Wincheater."
Jay 2-night trip
Posted 20 hours ago
Hampton Inn Winchester N/Conference Center, VA

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.