Find hotels in Old Town Winchester, 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, (1,001 reviews)
"The staff was helpful and kind. The architecture was incredible."
United States
Allison
The price is ₩223,046
₩252,712 total
includes taxes & fees
Jun 4 - Jun 5
The George Washington Hotel, A Wyndham Grand Hotel

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
2 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,004 reviews)
"Great location, clean rooms and friendly staff."
United States
Daniel
The price is ₩133,572
₩151,336 total
includes taxes & fees
Jun 2 - Jun 3
Spark by Hilton 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, (1,009 reviews)
"Location is right across the road from Spelunker's, the best casual restaurant in Virginia."
United States
Rachel
The price is ₩109,277
₩121,627 total
includes taxes & fees
May 24 - May 25
Super 8 by Wyndham Front Royal Near Shenandoah National Park

Relax Inn Motel

Relax Inn Motel
2.0 star property
27.6 km from Old Town Winchester
8.2 out of 10, Very Good, (275 reviews)
"The owners/managers are delightful. The room was very nice with excellent bedding. I look forward to staying there again "
United States
Sarah
The price is ₩97,302
₩108,305 total
includes taxes & fees
May 24 - May 25
Relax Inn Motel

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, (281 reviews)
"Very nice, clean room, comfortable bed, laminate floors for cleanliness. Great, warm staff, very helpful. I would stay again."
United States
Carol
The price is ₩95,430
₩107,836 total
includes taxes & fees
May 27 - May 28
Travelodge By Wyndham Charles Town/Harpers Ferry

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, (176 reviews)
"Everything about this special place is incredible."
United States
James
The price is ₩321,994
₩355,160 total
includes taxes & fees
May 26 - May 27
L'Auberge Provencale Inn & Restaurant

APM Inn & Suites

APM Inn & Suites
2.0 star property
2.3 km from Old Town Winchester
7.0 out of 10, Good, (446 reviews)
"Loved my stay there. Recommend"
United States
Deven
The price is ₩105,086
₩119,062 total
includes taxes & fees
Jun 6 - Jun 7
APM Inn & Suites

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)
"Best breakfast week had all week at a hotel. Friendly staff & clean rooms."
United States
Lauren
The price is ₩105,988
₩119,766 total
includes taxes & fees
Jun 8 - Jun 9
Days Inn by Wyndham Charles Town/Harpers Ferry

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
25 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,014 reviews)
"I enjoyed my stay. The room was clean and the breakfast was varied."
United States
Brenda
The price is ₩195,950
₩218,093 total
includes taxes & fees
Jun 7 - Jun 8
Hampton Inn Front Royal

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
4.3 km from Old Town Winchester
9.4 out of 10, Exceptional, (1,001 reviews)
"Breakfast was great and we love that they let us bring small dogs"
United States
Claire VanWinkle
The price is ₩138,692
₩150,897 total
includes taxes & fees
Jun 1 - Jun 2
Quality Inn Winchester

Hillbrook Inn

Hillbrook Inn
4.0 star property
21.7 km from Old Town Winchester
8.6 out of 10, Excellent, (677 reviews)
"Wonderful staff, and fall cottage was lovely."
United States
Henrik
The price is ₩238,015
₩304,001 total
includes taxes & fees
May 26 - May 27
Hillbrook Inn

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, (979 reviews)
"Beautiful hotel!"
United States
David
The price is ₩160,174
₩174,269 total
includes taxes & fees
Jun 11 - Jun 12
Courtyard 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, (871 reviews)
"Excellent hotel, great value!"
United States
Boris
The price is ₩170,622
₩185,636 total
includes taxes & fees
Jun 14 - Jun 15
TRU By Hilton Winchester

Home2 Suites By Hilton Winchester

Home2 Suites By Hilton Winchester
3.0 star property
3.6 km from Old Town Winchester
8.0 out of 10, Very Good, (6 reviews)
"There was no shampoo nor shower gel and the shower was cool water. Takes 5 minutes to even get lukewarm water. No one at front desk to check out so ??? "
United States
Timothy
The price is ₩158,718
₩179,828 total
includes taxes & fees
May 28 - May 29
Home2 Suites By Hilton Winchester

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, (1,001 reviews)
"Staff are so nice and everything was good"
United States
Osama
The price is ₩140,234
₩152,575 total
includes taxes & fees
Jun 14 - Jun 15
Country Inn & Suites by Radisson, Winchester, VA

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, (1,105 reviews)
"Neat place and excellent stay"
United States
Anoop
The price is ₩168,003
₩182,787 total
includes taxes & fees
Jun 9 - Jun 10
Comfort Inn & Suites Winchester

Blue Ridge Motel

Blue Ridge Motel
2.0 star property
27.9 km from Old Town Winchester
7.0 out of 10, Good, (134 reviews)
"Great lady that works there had a great time thanks again !!! Definitely will be back "
United States
William
The price is ₩87,572
₩97,482 total
includes taxes & fees
May 25 - May 26
Blue Ridge Motel

Motel 6 Front Royal, VA

Motel 6 Front Royal, VA
2.0 star property
27.7 km from Old Town Winchester
7.0 out of 10, Good, (516 reviews)
"Good location, good value, helpful staff. Would use the facility again"
United States
Robert
The price is ₩89,802
₩99,949 total
includes taxes & fees
May 26 - May 27
Motel 6 Front Royal, VA

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
25.8 km from Old Town Winchester
8.2 out of 10, Very Good, (1,003 reviews)
"Friendly staff and well maintained facilities. Great dog friendly property"
United States
Elaine
The price is ₩129,336
₩143,946 total
includes taxes & fees
May 24 - May 25
Ramada by Wyndham Strasburg/Shenandoah Valley

Twi-Lite Inn

Twi-Lite Inn
2.0 star property
27.8 km from Old Town Winchester
8.2 out of 10, Very Good, (553 reviews)
"The room was very clean and comfortable. We enjoyed our stay and enjoyed being able to pull up to the room and unload with no steps or elevator to get on."
United States
Lawanda
The price is ₩125,744
₩139,950 total
includes taxes & fees
May 28 - May 29
Twi-Lite Inn
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.

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

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.