A white neoclassical building with columns, an American flag, and a clock tower.

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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Filter by

Star rating

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Old Town Winchester hotels

Bar (on property)

1. 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)
"Great stay love the area very clean and staff was very helpful"
United States
Jeanette
The price is ₩177,108
₩200,664 total
includes taxes & fees
Sep 13 - Sep 14
The George Washington Hotel, A Wyndham Grand Hotel
Fitness facility

2. Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area
2.5 star property
2.1 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,001 reviews)
"I like the cleanliness of the room and the breakfast options."
United States
Henedina
The price is ₩149,272
₩169,124 total
includes taxes & fees
Sep 10 - Sep 11
Hampton Inn Winchester-University/Mall Area
Lobby

3. Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
2 km from Old Town Winchester
9.2 out of 10, Wonderful, (1,006 reviews)
"The staff was so friendly and the hotel was very clean"
United States
johnny
The price is ₩107,300
₩121,571 total
includes taxes & fees
Sep 29 - Sep 30
Spark by Hilton Winchester
Free daily buffet breakfast

4. 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, (2,279 reviews)
"Great stop over"
United States
Raquel
The price is ₩140,673
₩156,570 total
includes taxes & fees
Sep 6 - Sep 7
La Quinta Inn & Suites by Wyndham Winchester
Lobby

5. Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
2.9 km from Old Town Winchester
9.2 out of 10, Wonderful, (925 reviews)
"nice place to stay would recommend for others. very nice breakfast"
United States
Michael
The price is ₩125,856
₩140,078 total
includes taxes & fees
Oct 5 - Oct 6
Fairfield Inn & Suites by Marriott Winchester
Exterior

6. Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
3.2 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,001 reviews)
"Rooms very clean with comfortable beds after a long day of driving!"
United States
Jennifer
The price is ₩139,915
₩159,800 total
includes taxes & fees
Oct 4 - Oct 5
Holiday Inn Winchester Se-Historic Gateway by IHG
Interior

7. Hilton Garden Inn Winchester

Hilton Garden Inn Winchester
3.0 star property
2.1 km from Old Town Winchester
9.0 out of 10, Wonderful, (547 reviews)
"Very nice property."
United States
Don
The price is ₩158,184
₩179,222 total
includes taxes & fees
Sep 10 - Sep 11
Hilton Garden Inn Winchester
Lobby

8. 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, (1,067 reviews)
"Great staff, clean rooms and good breakfast."
United States
Jeffrey
The price is ₩103,246
₩113,883 total
includes taxes & fees
Sep 5 - Sep 6
Travelodge by Wyndham Winchester
Lobby

9. 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, (1,453 reviews)
"Excellent place"
United States
Ricky
The price is ₩117,374
₩130,637 total
includes taxes & fees
Sep 6 - Sep 7
Microtel Inn & Suites by Wyndham Winchester
Exterior

10. Quality Inn Winchester

Quality Inn Winchester
2.5 star property
4.3 km from Old Town Winchester
9.4 out of 10, Exceptional, (1,002 reviews)
"Nice breakfast, convenient location and helpful staff."
United States
Scott
The price is ₩108,544
₩120,810 total
includes taxes & fees
Sep 10 - Sep 11
Quality Inn Winchester
Pool

11. APM Inn & Suites

APM Inn & Suites
2.0 star property
2.3 km from Old Town Winchester
7.2 out of 10, Good, (491 reviews)
"Excellent staff and rooms. Will stay again"
United States
Teresa
The price is ₩93,532
₩105,972 total
includes taxes & fees
Sep 5 - Sep 6
APM Inn & Suites
Restaurant

12. 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, (929 reviews)
"Rooms were nice clean well stocked"
United States
Jackie
The price is ₩143,692
₩162,802 total
includes taxes & fees
Sep 13 - Sep 14
Hampton Inn Winchester N/Conference Center, VA
Exterior

13. 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, (1,001 reviews)
"Convenient location,"
United States
David
The price is ₩145,485
₩161,924 total
includes taxes & fees
Sep 29 - Sep 30
Courtyard by Marriott Winchester
Studio Suite, 1 Bedroom | In-room safe, desk, laptop workspace, blackout drapes

14. 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, (635 reviews)
"Loved the room and the bed was actually very comfortable. Very nice"
United States
Bridget
The price is ₩114,114
₩127,008 total
includes taxes & fees
Sep 6 - Sep 7
Candlewood Suites Winchester by IHG
Indoor pool

15. Holiday Inn Express Hotel & Suites Winchester by IHG

Holiday Inn Express Hotel & Suites Winchester by IHG
2.5 star property
3.1 km from Old Town Winchester
9.0 out of 10, Wonderful, (865 reviews)
"Clean room 👌 friendly staff"
United States
Gregory.
The price is ₩165,737
₩184,471 total
includes taxes & fees
Sep 13 - Sep 14
Holiday Inn Express Hotel & Suites Winchester by IHG
Lobby sitting area

16. Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
3.1 km from Old Town Winchester
7.8 out of 10, Good, (1,004 reviews)
"I have stayed here before, and will come again. This hotel always preforms well."
United States
Connor
The price is ₩104,441
₩116,243 total
includes taxes & fees
Sep 29 - Sep 30
Sleep Inn & Suites Winchester near University
Snack bar

17. TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
4.4 km from Old Town Winchester
9.2 out of 10, Wonderful, (1,004 reviews)
"Great stay"
United States
Gerley
The price is ₩121,423
₩135,144 total
includes taxes & fees
Sep 10 - Sep 11
TRU By Hilton Winchester
Lobby

18. 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, (1,002 reviews)
"Our stay here was wonderful! Very friendly and helpful staff. The cleanliness was excellent ! We will definitely stay here again."
United States
Nancy
The price is ₩134,916
₩150,162 total
includes taxes & fees
Sep 27 - Sep 28
Country Inn & Suites by Radisson, Winchester, VA
Exterior

19. 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, (895 reviews)
"Clean, receptive staff, great breakfast."
United States
Michael
The price is ₩154,217
₩171,644 total
includes taxes & fees
Sep 10 - Sep 11
SpringHill Suites by Marriott Winchester
Reception

20. 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, (524 reviews)
"The staff was friendly, the room was clean, amenities were sufficient and comparable to similar hotels. We had a very nice stay here."
United States
Katherine
The price is ₩153,578
₩170,932 total
includes taxes & fees
Sep 7 - Sep 8
TownePlace Suites by Marriott 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.
A red brick church with a blue door and a clock tower.
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

The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino

8/10 Good
"It was a decent hotel. The only thing I did not like was the four dollars I had to pay for a soda."
Nicholas 1-night trip
Posted 5 hours ago
The Inn at Charles Town - Hollywood Casino

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 Shenandoah Valley Discovery Museum and Bright Box Theater while you're in the neighborhood.
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 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.