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

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Check prices for these dates

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Oct 23 - Oct 25
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Oct 30 - Nov 1

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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, (1,003 reviews)
"The room was very comfortable. Uno's was a wonderful place to eat!"
United States
Carol
The price is ₩173,542
₩196,624 total
includes taxes & fees
Oct 28 - Oct 29
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, (2,276 reviews)
"Great place to stay the night after a long drive"
United States
lucy
The price is ₩136,894
₩152,371 total
includes taxes & fees
Oct 21 - Oct 22
La Quinta Inn & Suites by Wyndham Winchester
A modern hotel room with a bed, sofa, and a small table. There are two doors, one blue and one white, and a small table with chairs.

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, (1,012 reviews)
"Very nice and welcoming staff, nice location, pool and included breakfast available!"
United States
carrie
The price is ₩101,817
₩115,359 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, (1,445 reviews)
"Loved our stay, it was well priced and had everything we needed!"
United States
Christopher
The price is ₩111,808
₩124,443 total
includes taxes & fees
Nov 15 - Nov 16
Microtel Inn & Suites by Wyndham Winchester
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.

5. 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, (1,013 reviews)
"For the price we could not ask for more......well run hotel.....thanks!"
United States
Jeffrey
The price is ₩131,774
₩150,657 total
includes taxes & fees
Nov 17 - Nov 18
Holiday Inn Winchester Se-Historic Gateway by IHG
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, (1,001 reviews)
"We had an amazing stay and will be back! The rooms were clean and comfy and staff were very helpful."
United States
Jessica
The price is ₩142,555
₩158,663 total
includes taxes & fees
Oct 26 - Oct 27
Courtyard by Marriott Winchester
A hotel room with two beds, a desk, a TV, and a window with a view.

7. 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, (956 reviews)
"Clean room and quiet and breakfast great"
United States
Michael
The price is ₩140,798
₩159,525 total
includes taxes & fees
Nov 3 - Nov 4
Hampton Inn Winchester N/Conference Center, VA
A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.

8. 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, (954 reviews)
"Great place to stay in Winchester."
United States
Thomas
The price is ₩123,322
₩137,256 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Winchester
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, (1,009 reviews)
"Hotel was very clean and breakfast was delicious with a lot of options"
United States
Kailyn
The price is ₩113,512
₩126,339 total
includes taxes & fees
Nov 1 - Nov 2
TRU By Hilton Winchester
A modern dining area with a large white table, blue chairs, and a flat-screen TV mounted on the wall.

10. 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)
"Very clean comfortable bed good breakfast"
United States
David
The price is ₩150,409
₩167,405 total
includes taxes & fees
Nov 18 - Nov 19
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.

11. 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, (1,138 reviews)
"Location off the highway..clean room, helpful staff"
United States
Lisa
The price is ₩133,584
₩148,679 total
includes taxes & fees
Nov 15 - Nov 16
Comfort Inn & Suites Winchester
An outdoor patio with a fire feature, seating, and a covered area.

12. 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, (910 reviews)
"Clean, receptive staff, great breakfast."
United States
Michael
The price is ₩151,101
₩168,176 total
includes taxes & fees
Nov 8 - Nov 9
SpringHill Suites by Marriott 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, (611 reviews)
"Had an absolute great stay."
United States
Justin
The price is ₩185,016
₩206,735 total
includes taxes & fees
Nov 9 - Nov 10
TownePlace Suites by Marriott Front Royal
A spacious hotel dining area with multiple tables and chairs, large windows, and a kitchen area visible in the background.

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, (557 reviews)
"Clean room, easy on and off, coffee and water complimentary"
United States
Wendy
The price is ₩162,921
₩184,589 total
includes taxes & fees
Oct 29 - Oct 30
Hilton Garden Inn Winchester
A spacious living room with a fireplace, wooden staircase, and a bookshelf.

15. 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, (1,007 reviews)
"Great stay."
United States
Allen
The price is ₩117,665
₩130,962 total
includes taxes & fees
Nov 15 - Nov 16
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.

16. 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, (1,077 reviews)
"Very nice stay great staff and very clean"
United States
john
The price is ₩94,505
₩104,235 total
includes taxes & fees
Nov 1 - Nov 2
Travelodge by Wyndham Winchester
Exterior

17. 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, (1,002 reviews)
"I like the cleanliness of the room and the breakfast options."
United States
Henedina
The price is ₩127,847
₩144,851 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Winchester-University/Mall Area
A restaurant interior with a bar area, seating, and artwork on the walls.

18. 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, (1,003 reviews)
"Clean, quiet and reasonably priced hotel!"
United States
Jeffrey
The price is ₩171,104
₩188,727 total
includes taxes & fees
Nov 11 - Nov 12
DoubleTree by Hilton Front Royal Blue Ridge Shadows
A modern hotel with a covered outdoor area, landscaped gardens, and a parking lot.

19. Quality Inn Winchester

Quality Inn Winchester
2.5 star property
4.3 km from Old Town Winchester
9.4 out of 10, Exceptional, (1,014 reviews)
"Welcoming Staff, clean room at a good price."
United States
DARLA
The price is ₩104,887
₩116,739 total
includes taxes & fees
Nov 15 - Nov 16
Quality Inn Winchester
A buffet with labeled containers of turkey sausage and cookies.

20. Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
12.4 km from Old Town Winchester
8.2 out of 10, Very good, (916 reviews)
"Great hotel"
United States
Michael
The price is ₩115,801
₩128,887 total
includes taxes & fees
Nov 19 - Nov 20
Holiday Inn Express Winchester South-Stephens City 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.
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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

Hampton Inn Front Royal

Hampton Inn Front Royal

10/10 Excellent
"Clean"
Fang 1-night trip
Posted 5 hours ago
Hampton Inn Front Royal

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.