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 18 - Sep 20
Next weekend
Sep 25 - Sep 27

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, (1,001 reviews)
"Great stay love the area very clean and staff was very helpful"
United States
Jeanette
The price is ₩177,716
₩201,352 total
includes taxes & fees
Sep 27 - Sep 28
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 ₩144,184
₩163,361 total
includes taxes & fees
Sep 23 - Sep 24
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, (1,001 reviews)
"Great stay"
Canada
Peter
The price is ₩105,065
₩119,039 total
includes taxes & fees
Sep 28 - Sep 29
Spark by Hilton Winchester
Breakfast area

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, (2,272 reviews)
"Nice room, good breakfast. Friendly staff, definitely would stay here again."
United States
Earl
The price is ₩155,389
₩172,947 total
includes taxes & fees
Sep 20 - Sep 21
La Quinta Inn & Suites by Wyndham Winchester
Interior

5. 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, (554 reviews)
"Clean room, easy on and off, coffee and water complimentary"
United States
Wendy
The price is ₩136,361
₩154,497 total
includes taxes & fees
Sep 28 - Sep 29
Hilton Garden Inn Winchester
Lobby

6. 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, (933 reviews)
"nice place to stay would recommend for others. very nice breakfast"
United States
Michael
The price is ₩126,288
₩140,559 total
includes taxes & fees
Sep 27 - Sep 28
Fairfield Inn & Suites by Marriott Winchester
Lobby

7. 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, (1,073 reviews)
"Place was good was there 4 nights national park was close and anything u need was close"
United States
Pietro
The price is ₩94,051
₩103,742 total
includes taxes & fees
Sep 20 - Sep 21
Travelodge by Wyndham Winchester
Exterior

8. 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 ₩143,121
₩163,383 total
includes taxes & fees
Sep 20 - Sep 21
Holiday Inn Winchester Se-Historic Gateway by IHG
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, (1,448 reviews)
"Great place to stop during road trip, breakfast was satisfying and coffee was good"
United States
Katheryne
The price is ₩122,130
₩135,931 total
includes taxes & fees
Sep 22 - Sep 23
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 ₩114,701
₩127,662 total
includes taxes & fees
Sep 23 - Sep 24
Quality Inn Winchester
Exterior

11. 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)
"This place was so well kept up amd clean. I hope to stay there again when traveling"
United States
Karen
The price is ₩145,984
₩162,480 total
includes taxes & fees
Sep 23 - Sep 24
Courtyard by Marriott Winchester
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, (933 reviews)
"Rooms were nice clean well stocked"
United States
Jackie
The price is ₩144,184
₩163,361 total
includes taxes & fees
Sep 23 - Sep 24
Hampton Inn Winchester N/Conference Center, VA
Exterior

13. 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, (867 reviews)
"Clean room 👌 friendly staff"
United States
Gregory.
The price is ₩162,486
₩180,847 total
includes taxes & fees
Oct 18 - Oct 19
Holiday Inn Express Hotel & Suites Winchester by IHG
Studio Suite, 1 Bedroom

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, (641 reviews)
"Loved the room and the bed was actually very comfortable. Very nice"
United States
Bridget
The price is ₩114,497
₩127,435 total
includes taxes & fees
Sep 20 - Sep 21
Candlewood Suites Winchester by IHG
Lobby sitting area

15. Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
3.1 km from Old Town Winchester
7.6 out of 10, Good, (1,001 reviews)
"I have stayed here before, and will come again. This hotel always preforms well."
United States
Connor
The price is ₩104,274
₩116,058 total
includes taxes & fees
Oct 12 - Oct 13
Sleep Inn & Suites Winchester near University
Reception

16. 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, (525 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 ₩154,094
₩171,507 total
includes taxes & fees
Sep 24 - Sep 25
TownePlace Suites by Marriott Winchester
Lobby

17. 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)
"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 ₩140,619
₩156,509 total
includes taxes & fees
Oct 11 - Oct 12
Country Inn & Suites by Radisson, Winchester, VA
Exterior

18. 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, (900 reviews)
"Clean, receptive staff, great breakfast."
United States
Michael
The price is ₩166,729
₩185,569 total
includes taxes & fees
Sep 27 - Sep 28
SpringHill Suites by Marriott Winchester
Pool

19. APM Inn & Suites

APM Inn & Suites
2.0 star property
2.3 km from Old Town Winchester
7.0 out of 10, Good, (500 reviews)
"Not a bad place to stay."
United States
Edward
The price is ₩79,739
₩90,345 total
includes taxes & fees
Oct 1 - Oct 2
APM Inn & Suites
Snack bar

20. 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, (1,009 reviews)
"Great stay"
United States
Gerley
The price is ₩127,419
₩141,817 total
includes taxes & fees
Sep 27 - Sep 28
TRU By Hilton 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

Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"The hotel is conveniently located, clean, pleasant and very reasonably priced. It was just what we needed for an overnight stop with a dog."
Neiri 1-night trip
Posted 2 hours ago
Quality Inn Winchester

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 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.