Old Town Winchester Hotels, Winchester

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Old Town Winchester hotels

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 AU$214
includes taxes & fees
28 Jan - 29 Jan
The George Washington Hotel, A Wyndham Grand Hotel

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, (2,249 reviews)
"yes, room was spotless very nice place to stay"
United States
ROBERT
The price is AU$149
includes taxes & fees
21 Jan - 22 Jan
La Quinta Inn & Suites by Wyndham Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
7.8 km from Old Town Winchester
9.4 out of 10, Exceptional, (1,096 reviews)
"We have stayed here many times on our way to Massachusetts and find it perfect every time."
United States
Patsy
The price is AU$159
includes taxes & fees
8 Feb - 9 Feb
Comfort Inn & Suites 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, (815 reviews)
"We stay here a lot and it is always consistently clean and service is great. "
United States
Kim
The price is AU$150
includes taxes & fees
25 Jan - 26 Jan
Fairfield Inn & Suites by Marriott Winchester

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, (1,000 reviews)
"Nice place to stay"
United States
Cynthia
The price is AU$112
includes taxes & fees
25 Jan - 26 Jan
Days Inn by Wyndham Charles Town/Harpers Ferry

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, (1,002 reviews)
"Certainly will stay again "
United States
philip
The price is AU$107
includes taxes & fees
2 Feb - 3 Feb
Rodeway Inn & Suites Charles Town

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, (533 reviews)
"Friendly staff, comfortable bed, convenient location "
United States
Kourtney
The price is AU$207
includes taxes & fees
27 Jan - 28 Jan
The Inn at Charles Town - Hollywood Casino

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
4.3 km from Old Town Winchester
9.2 out of 10, Wonderful, (1,000 reviews)
"Great stay, as usual"
United States
Mary
The price is AU$135
includes taxes & fees
6 Feb - 7 Feb
Quality Inn 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, (1,438 reviews)
"Clean, spacious room with friendly staff and good breakfast..... would stay there again for sure!"
United States
Eleanor
The price is AU$132
includes taxes & fees
26 Jan - 27 Jan
Microtel Inn & Suites by Wyndham Winchester

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
2 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,001 reviews)
"Good hotel on our road trip"
United States
Janet
The price is AU$130
includes taxes & fees
8 Feb - 9 Feb
Spark by Hilton Winchester

Hillbrook Inn

Hillbrook Inn
4.0 star property
21.7 km from Old Town Winchester
8.6 out of 10, Excellent, (673 reviews)
"Wonderful staff, and fall cottage was lovely."
United States
Henrik
The price is AU$289
includes taxes & fees
26 Jan - 27 Jan
Hillbrook Inn

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, (799 reviews)
"Great stay!"
United States
Rene
The price is AU$174
includes taxes & fees
1 Feb - 2 Feb
SpringHill Suites by Marriott 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, (789 reviews)
"Clean room, good breakfast, easy check in/out."
United States
Joseph
The price is AU$145
includes taxes & fees
26 Jan - 27 Jan
TRU By Hilton Winchester

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
2.9 km from Old Town Winchester
8.6 out of 10, Excellent, (1,068 reviews)
"Hotels well Located off 81 for a nice pull Off and overnight stay. Staff is friendly and helpful and rooms comfortable and quiet. "
United States
Stefanie
The price is AU$113
includes taxes & fees
21 Jan - 22 Jan
Travelodge by Wyndham Winchester

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
7.0 out of 10, Good, (266 reviews)
"Room was very clean and quiet!"
United States
Mary ann
The price is AU$107
includes taxes & fees
21 Jan - 22 Jan
Travelodge By Wyndham Charles Town/Harpers Ferry

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, (1,000 reviews)
"Great room and staff. Nice restaurant and bar also with good prices. Very nice hotel. 5 stars"
United States
Vincent
The price is AU$160
includes taxes & fees
8 Feb - 9 Feb
DoubleTree by Hilton Front Royal Blue Ridge Shadows

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
7.5 km from Old Town Winchester
8.8 out of 10, Excellent, (1,000 reviews)
"Clean efficient room with good front desk service. Convienence to Highway 81 and eateries."
United States
Chris
The price is AU$133
includes taxes & fees
8 Feb - 9 Feb
Country Inn & Suites by Radisson, Winchester, VA

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
25 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,002 reviews)
"Room was spotless, place was quiet and our welcome at the desk was perfect"
United States
Merrill
The price is AU$162
includes taxes & fees
15 Feb - 16 Feb
Hampton Inn Front Royal

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, (927 reviews)
"Room was great. Staff was extremely friendly."
United States
Amy
The price is AU$173
includes taxes & fees
27 Jan - 28 Jan
Courtyard by Marriott Winchester

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 AU$103
includes taxes & fees
21 Jan - 22 Jan
Super 8 by Wyndham Front Royal Near Shenandoah National Park
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.

Our guide on where to stay in Old Town Winchester

Find the best Old Town Winchester areas 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 Handley Regional Library.

Top Old Town Winchester Hotel Reviews

Frequently asked questions

What is Old Town Winchester like?
Old Town Winchester is an historic neighbourhood known for its array of dining options. Are you looking for Old Town Winchester travel tips? Make sure that you visit Bright Box Theater and Shenandoah Valley Discovery Museum while you're in the neighbourhood.
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 should I expect to find in the Old Town Winchester area?
With 12 Expedia hotels and other accommodation options 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, the majority of room reservations are fully refundable provided that you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of your booking. Enter dates in and click on "Search", then use the filter option "fully refundable" to review the best deals available in Old Town Winchester.
What is there to do around this Winchester neighbourhood?
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 worth a visit in the neighbourhood. 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.

Explore a world of travel with Expedia