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
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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

A courtyard with a fountain, tables with white tablecloths, and brick buildings.

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, (1,000 reviews)
"The room was very comfortable. Uno's was a wonderful place to eat!"
United States
Carol
The price is ₩175,055
₩198,337 total
includes taxes & fees
Oct 29 - Oct 30
The George Washington Hotel, A Wyndham Grand Hotel
A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.

2. 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, (2,266 reviews)
"Great place to stay the night after a long drive"
United States
lucy
The price is ₩131,822
₩146,717 total
includes taxes & fees
Oct 18 - Oct 19
La Quinta Inn & Suites by Wyndham Winchester
A spacious lobby with a checkered floor, yellow chairs, a green carpet, and a wall with the text "It only takes a spark".

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, (1,002 reviews)
"Very nice and welcoming staff, nice location, pool and included breakfast available!"
United States
carrie
The price is ₩103,491
₩117,255 total
includes taxes & fees
Nov 2 - Nov 3
Spark by Hilton Winchester
A modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.

4. 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, (1,447 reviews)
"Great place to stop during road trip, breakfast was satisfying and coffee was good"
United States
Katheryne
The price is ₩112,783
₩125,526 total
includes taxes & fees
Nov 15 - Nov 16
Microtel Inn & Suites by Wyndham Winchester
A gym with treadmills, exercise balls, and a mirrored wall.

5. 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, (1,000 reviews)
"I like the cleanliness of the room and the breakfast options."
United States
Henedina
The price is ₩130,209
₩147,527 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Winchester-University/Mall Area
A Courtyard by Marriott hotel with a covered entrance, multiple floors, and a brick facade.

6. 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, (1,000 reviews)
"Very clean, very comfortable beds, generous room good pillow, selection, clean, and roomy bathroom"
United States
John
The price is ₩143,798
₩160,047 total
includes taxes & fees
Oct 22 - Oct 23
Courtyard by Marriott Winchester
A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.

7. 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, (952 reviews)
"Great place to stay in Winchester."
United States
Thomas
The price is ₩124,397
₩138,454 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Winchester
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.

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, (1,003 reviews)
"For the price we could not ask for more......well run hotel.....thanks!"
United States
Jeffrey
The price is ₩132,922
₩151,970 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Winchester Se-Historic Gateway by IHG
A self-service beverage station with a refrigerated drink dispenser, a coffee machine, and a variety of snacks.

9. 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)
"Hotel was very clean and breakfast was delicious with a lot of options"
United States
Kailyn
The price is ₩114,501
₩127,439 total
includes taxes & fees
Nov 1 - Nov 2
TRU By Hilton Winchester
An outdoor patio with a fire feature, seating, and a covered area.

10. 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, (908 reviews)
"Clean, receptive staff, great breakfast."
United States
Michael
The price is ₩152,418
₩169,641 total
includes taxes & fees
Nov 8 - Nov 9
SpringHill Suites by Marriott Winchester
A modern dining area with a large white table, blue chairs, and a flat-screen TV mounted on the wall.

11. 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, (869 reviews)
"Clean room 👌 friendly staff"
United States
Gregory.
The price is ₩147,692
₩164,381 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Hotel & Suites Winchester by IHG
A Comfort Inn & Suites building with a modern design, featuring a prominent logo on the facade, a covered entrance, and multiple windows.

12. 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, (1,139 reviews)
"Great location with easy access to nice dining. Very courteous staff."
United States
John
The price is ₩134,265
₩149,437 total
includes taxes & fees
Nov 5 - Nov 6
Comfort Inn & Suites Winchester
An outdoor seating area with a fire feature, wicker furniture, and a building with multiple windows.

13. 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, (609 reviews)
"Had an absolute great stay."
United States
Justin
The price is ₩186,628
₩208,536 total
includes taxes & fees
Nov 1 - Nov 2
TownePlace Suites by Marriott Front Royal
A hotel room with a large bed, a desk with a chair, a small table, a chair, a lamp, and a picture on the wall.

14. 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, (556 reviews)
"Clean room, easy on and off, coffee and water complimentary"
United States
Wendy
The price is ₩162,191
₩183,763 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Winchester
A hotel room with two beds, a desk, a TV, and a window with a view.

15. 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, (952 reviews)
"Clean room and quiet and breakfast great"
United States
Michael
The price is ₩142,026
₩160,915 total
includes taxes & fees
Oct 29 - Oct 30
Hampton Inn Winchester N/Conference Center, VA
A restaurant interior with a bar area, seating, and artwork on the walls.

16. 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, (1,002 reviews)
"Always a great stay when golfing at Blue Ridge Shadows!"
United States
Brian
The price is ₩164,045
₩180,941 total
includes taxes & fees
Nov 2 - Nov 3
DoubleTree by Hilton Front Royal Blue Ridge Shadows
A spacious living room with a fireplace, wooden staircase, and a bookshelf.

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, (1,001 reviews)
"Great stay."
United States
Allen
The price is ₩118,475
₩131,864 total
includes taxes & fees
Nov 8 - Nov 9
Country Inn & Suites by Radisson, Winchester, VA
A modern living room with a sofa, armchair, dining table, and chairs. There is a TV mounted on the wall and a small table with a lamp.

18. 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, (1,083 reviews)
"Very nice stay great staff and very clean"
United States
john
The price is ₩95,328
₩105,143 total
includes taxes & fees
Nov 10 - Nov 11
Travelodge by Wyndham Winchester
A hotel lobby with a reception desk, seating area with a round table, and a bar.

19. 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, (1,000 reviews)
"Very affordable, nice rooms, and conveniently located - greatly enjoyed our stay!"
United States
Patrick
The price is ₩151,787
₩168,938 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites Strasburg Shenandoah Valley
A hotel room with a bed, a brown sofa, a round table, a lamp, a window with a decorative screen, and a framed picture on the wall.

20. 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, (652 reviews)
"Nice place to stay. Convenient for our travels."
United States
marilyn
The price is ₩107,412
₩119,550 total
includes taxes & fees
Nov 15 - Nov 16
Candlewood Suites Winchester by IHG
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

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

10/10 Excellent
"The room was clean and big. The breakfast had a nice variety."
Donna 1-night trip
Posted 6 hours ago
Ramada by Wyndham Strasburg/Shenandoah Valley

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.