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
Next weekend
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, (1,004 reviews)
"The room was very comfortable. Uno's was a wonderful place to eat!"
United States
Carol
The price is ₩172,982
₩195,988 total
includes taxes & fees
Nov 8 - Nov 9
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, (2,278 reviews)
"Great place to stay the night after a long drive"
United States
lucy
The price is ₩136,566
₩151,998 total
includes taxes & fees
Oct 22 - Oct 23
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, (1,000 reviews)
"Very nice and welcoming staff, nice location, pool and included breakfast available!"
United States
carrie
The price is ₩100,454
₩113,815 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 ₩111,447
₩124,040 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, (1,014 reviews)
"For the price we could not ask for more......well run hotel.....thanks!"
United States
Jeffrey
The price is ₩131,348
₩150,171 total
includes taxes & fees
Nov 18 - Nov 19
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 ₩142,095
₩158,151 total
includes taxes & fees
Nov 1 - Nov 2
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 ₩140,344
₩159,009 total
includes taxes & fees
Oct 29 - Oct 30
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 ₩122,923
₩136,813 total
includes taxes & fees
Nov 3 - Nov 4
Fairfield Inn & Suites by Marriott Winchester
A Comfort Inn & Suites building with a modern design, featuring a prominent logo on the facade, a covered entrance, and multiple windows.

9. 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 ₩133,153
₩148,199 total
includes taxes & fees
Nov 15 - Nov 16
Comfort Inn & Suites 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, (910 reviews)
"Clean, receptive staff, great breakfast."
United States
Michael
The price is ₩150,613
₩167,632 total
includes taxes & fees
Nov 18 - Nov 19
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)
"Very clean comfortable bed good breakfast"
United States
David
The price is ₩149,923
₩166,864 total
includes taxes & fees
Nov 18 - Nov 19
Holiday Inn Express Hotel & Suites Winchester by IHG
A hotel lobby with seating, a reception desk, and a refrigerated display.

12. 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, (531 reviews)
"Always a great place to land!! Love the location!! Great walking areas, a grocery store and lots of restaurants within walking distance!! Many many good wineries as well!!"
United States
Lori
The price is ₩149,989
₩166,937 total
includes taxes & fees
Oct 26 - Oct 27
TownePlace Suites by Marriott Winchester
A spacious living room with a fireplace, wooden staircase, and a bookshelf.

13. 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, (1,009 reviews)
"Great stay."
United States
Allen
The price is ₩117,285
₩130,538 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.

14. 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 ₩94,199
₩103,898 total
includes taxes & fees
Nov 1 - Nov 2
Travelodge by Wyndham Winchester
A modern hotel with a covered outdoor area, landscaped gardens, and a parking lot.

15. Quality Inn Winchester

Quality Inn Winchester
2.5 star property
4.3 km from Old Town Winchester
9.4 out of 10, Exceptional, (1,015 reviews)
"Welcoming Staff, clean room at a good price."
United States
DARLA
The price is ₩104,601
₩116,421 total
includes taxes & fees
Nov 15 - Nov 16
Quality Inn Winchester
A lobby with a green wall, a reception desk, and seating area with sofas and armchairs.

16. Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
3.1 km from Old Town Winchester
7.6 out of 10, Good, (1,003 reviews)
"I have stayed here before, and will come again. This hotel always preforms well."
United States
Connor
The price is ₩107,467
₩119,611 total
includes taxes & fees
Nov 1 - Nov 2
Sleep Inn & Suites Winchester near University
A gym with exercise equipment, including a bench, red exercise balls, and a variety of weights.

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 hotel lobby with a reception desk, seating area with a round table, and a bar.

18. 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, (1,002 reviews)
"Very affordable, nice rooms, and conveniently located - greatly enjoyed our stay!"
United States
Patrick
The price is ₩150,475
₩167,478 total
includes taxes & fees
Nov 8 - Nov 9
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.

19. 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, (655 reviews)
"Nice place to stay. Convenient for our travels."
United States
marilyn
The price is ₩106,484
₩118,517 total
includes taxes & fees
Nov 8 - Nov 9
Candlewood Suites Winchester by IHG
A spacious dining area with round tables and chairs, a large potted plant, and a wall with artwork.

20. The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino
3.0 star property
30 km from Old Town Winchester
8.6 out of 10, Excellent, (644 reviews)
"The staff and place were great, with a shuttle running back and forth to the casino."
United States
HARRY
The price is ₩159,197
₩191,567 total
includes taxes & fees
Nov 18 - Nov 19
The Inn at Charles Town - Hollywood Casino
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

Compare popular hotels in Old Town Winchester

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
A courtyard with a fountain, tables with white tablecloths, and brick buildings.
The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
9.4
Exceptional
1,004 reviews
View
A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.
La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
9.2
Wonderful
2,278 reviews
View
A spacious lobby with a checkered floor, yellow chairs, a green carpet, and a wall with the text "It only takes a spark".
Spark by Hilton Winchester
3.0 star property
9.2
Wonderful
1,000 reviews
View
A hotel room with two beds, a desk, a TV, and a window with a view.
Hampton Inn Winchester N/Conference Center, VA
2.5 star property
9.2
Wonderful
956 reviews
View
A hotel room with a desk, chair, sofa, ottoman, lamp, and a bed.
Home2 Suites By Hilton Winchester
3.0 star property
9.2
Wonderful
37 reviews
View

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

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"we had a large , very clean and air conditioned room. The reception was easy and very friendly and the breakfast was quick and easy"
Robert 1-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Winchester, VA

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.