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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
3 Apr - 4 Apr
Tomorrow
4 Apr - 5 Apr
This weekend
3 Apr - 5 Apr
Next weekend
10 Apr - 12 Apr

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
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1,002 reviews)
"Location of hotel is great for walking to restaurants and shops. "
United States
Paul
The price is NZ$242
includes taxes & fees
27 Apr - 28 Apr
The George Washington Hotel, A Wyndham Grand Hotel
Restaurant

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, (870 reviews)
"The staff was wonderful! "
United States
Jayne
The price is NZ$209
includes taxes & fees
18 Apr - 19 Apr
Hampton Inn Winchester N/Conference Center, VA
Free daily buffet breakfast

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, (2,270 reviews)
"Very nice would stay there again"
United States
John
The price is NZ$208
includes taxes & fees
15 Apr - 16 Apr
La Quinta Inn & Suites by Wyndham Winchester
Exterior

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, (1,092 reviews)
"Overall a pleasant stay!"
United States
Mark
The price is NZ$196
includes taxes & fees
26 Apr - 27 Apr
Comfort Inn & Suites Winchester
2 bars/lounges, sports bar

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, (1,004 reviews)
"Clean room, super friendly people, great breakfast, and the shuttle was awesome!"
United States
India
The price is NZ$134
includes taxes & fees
19 Apr - 20 Apr
Rodeway Inn & Suites Charles Town
Room, 1 King Bed, Non Smoking

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, (273 reviews)
"Decent continental breakfast. Night staff is friendly and helpful. Accessible. "
United States
David
The price is NZ$125
includes taxes & fees
8 Apr - 9 Apr
Travelodge By Wyndham Charles Town/Harpers Ferry
Front of property

Hillbrook Inn

Hillbrook Inn
4.0 star property
21.7 km from Old Town Winchester
8.6 out of 10, Excellent, (676 reviews)
"Wonderful staff, and fall cottage was lovely."
United States
Henrik
The price is NZ$357
includes taxes & fees
21 Apr - 22 Apr
Hillbrook Inn
Lobby

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
2.9 km from Old Town Winchester
9.0 out of 10, Wonderful, (835 reviews)
"We stay here a lot and it is always consistently clean and service is great. "
United States
Kim
The price is NZ$175
includes taxes & fees
14 Apr - 15 Apr
Fairfield Inn & Suites by Marriott Winchester
Exterior

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, (829 reviews)
"Beautiful hotel and room. Accessible room was perfect. Staff was friendly right from check-in. Would highly recommend this hotel to anyone who needs an accessible room. "
United States
Andrew
The price is NZ$216
includes taxes & fees
19 Apr - 20 Apr
SpringHill Suites by Marriott Winchester
Property amenity

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, (568 reviews)
"Clean room, friendly and helpful staff, good breakfast, I would stay again."
United States
Catherine
The price is NZ$247
includes taxes & fees
19 Apr - 20 Apr
TownePlace Suites by Marriott Front Royal
Exterior

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
4.3 km from Old Town Winchester
9.2 out of 10, Wonderful, (1,002 reviews)
"Everything was perfect. Would highly recommend this hotel"
Canada
Phyllis
The price is NZ$175
includes taxes & fees
14 Apr - 15 Apr
Quality Inn Winchester
Indoor pool

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
25 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,000 reviews)
"All the staff members were so nice and kind!! The hotel room I booked were very clean and spotless, and the breakfast was even fresh too!"
United States
Kenny
The price is NZ$198
includes taxes & fees
26 Apr - 27 Apr
Hampton Inn Front Royal
Lobby

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)
"Very clean rooms and friendly staff."
United States
Christine
The price is NZ$174
includes taxes & fees
26 Apr - 27 Apr
Country Inn & Suites by Radisson, Winchester, VA
Exterior

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, (950 reviews)
"Great location"
Canada
jim
The price is NZ$202
includes taxes & fees
24 Apr - 25 Apr
Courtyard by Marriott Winchester
Porch

Relax Inn Motel

Relax Inn Motel
2.0 star property
27.6 km from Old Town Winchester
8.2 out of 10, Very good, (263 reviews)
"On my way back from shenendoah and Luray to dc place was fine "
United States
tara
The price is NZ$120
includes taxes & fees
12 Apr - 13 Apr
Relax Inn Motel
Lobby

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
2 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,002 reviews)
"Nice staff, clean with a convenient location make it a good choice for a stay in Winchester. "
United States
Mira
The price is NZ$171
includes taxes & fees
19 Apr - 20 Apr
Spark by Hilton Winchester
Seasonal outdoor pool

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
27.8 km from Old Town Winchester
8.2 out of 10, Very good, (548 reviews)
"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 NZ$145
includes taxes & fees
15 Apr - 16 Apr
Twi-Lite Inn
Lobby

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)
"Very accessible to restaurants and stores"
United States
Scott
The price is NZ$134
includes taxes & fees
29 Apr - 30 Apr
Days Inn by Wyndham Charles Town/Harpers Ferry
Lobby lounge

Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley
3.0 star property
24.9 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,002 reviews)
"Asked for quiet floor after a long week of travels for work and he put me on the 4th floor Was super quiet , super clean and breakfast was decent,"
United States
angie
The price is NZ$220
includes taxes & fees
20 Apr - 21 Apr
Fairfield Inn & Suites Strasburg Shenandoah Valley
Lobby

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, (1,455 reviews)
"Everything,room was amazing, staff so friendly, breakfast very good "
United States
Douglas Gary
The price is NZ$169
includes taxes & fees
28 Apr - 29 Apr
Microtel Inn & Suites by Wyndham 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

Our guide on where to stay in Old Town Winchester

Find the best Old Town Winchester areas for the activities you enjoy most.
Photo by Fernando Begay
Open Photo by Fernando Begay

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

Days Inn by Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry

4/10 Poor
"Bathroom had mold all around the bathtub. Tv remote didnt work. AC was barely functional. Whole place looked like it charged by the hour"
Mack 1-night trip
Posted 6 hours ago
Days Inn by Wyndham Charles Town/Harpers Ferry

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