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

Search 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

Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

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, (1,002 reviews)
"The room was very comfortable. Uno's was a wonderful place to eat!"
United States
Carol
The price is ฿4,375
฿4,957 total
includes taxes & fees
11 Oct - 12 Oct
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, (2,272 reviews)
"Nice room, good breakfast. Friendly staff, definitely would stay here again."
United States
Earl
The price is ฿3,624
฿4,034 total
includes taxes & fees
25 Oct - 26 Oct
La Quinta Inn & Suites by Wyndham Winchester
A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.

3. 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, (944 reviews)
"Great stay"
United States
Dawn
The price is ฿3,109
฿3,461 total
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Winchester
A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.

4. 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, (944 reviews)
"Clean room and quiet and breakfast great"
United States
Michael
The price is ฿3,550
฿4,022 total
includes taxes & fees
11 Oct - 12 Oct
Hampton Inn Winchester N/Conference Center, VA
A spacious lobby with a checkered floor, yellow chairs, a green carpet, and a wall with the text "It only takes a spark".

5. Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
2 km from Old Town Winchester
9.2 out of 10, Wonderful, (1,005 reviews)
"Very nice and welcoming staff, nice location, pool and included breakfast available!"
United States
carrie
The price is ฿2,595
฿2,941 total
includes taxes & fees
2 Nov - 3 Nov
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.

6. 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)
"Very clean hotel and rooms. Breakfast was very good too!"
United States
Marcia
The price is ฿3,087
฿3,436 total
includes taxes & fees
1 Nov - 2 Nov
Microtel Inn & Suites by Wyndham Winchester
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.

7. 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, (1,006 reviews)
"For the price we could not ask for more......well run hotel.....thanks!"
United States
Jeffrey
The price is ฿3,322
฿3,798 total
includes taxes & fees
1 Nov - 2 Nov
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.

8. 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, (1,003 reviews)
"Hotel was very clean and breakfast was delicious with a lot of options"
United States
Kailyn
The price is ฿3,000
฿3,338 total
includes taxes & fees
1 Nov - 2 Nov
TRU By Hilton Winchester
A Courtyard by Marriott hotel with a covered entrance, multiple floors, and a brick facade.

9. 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, (1,003 reviews)
"Very clean, very comfortable beds, generous room good pillow, selection, clean, and roomy bathroom"
United States
John
The price is ฿3,394
฿3,778 total
includes taxes & fees
18 Oct - 19 Oct
Courtyard 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.

10. 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, (1,134 reviews)
"Great location with easy access to nice dining. Very courteous staff."
United States
John
The price is ฿3,309
฿3,683 total
includes taxes & fees
11 Oct - 12 Oct
Comfort Inn & Suites Winchester
An outdoor patio with a fire feature, seating, and a covered area.

11. 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, (903 reviews)
"Clean, receptive staff, great breakfast."
United States
Michael
The price is ฿4,105
฿4,569 total
includes taxes & fees
1 Nov - 2 Nov
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.

12. 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, (868 reviews)
"Clean room 👌 friendly staff"
United States
Gregory.
The price is ฿3,960
฿4,407 total
includes taxes & fees
4 Nov - 5 Nov
Holiday Inn Express Hotel & Suites Winchester by IHG
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.

13. 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)
"Very nice stay great staff and very clean"
United States
john
The price is ฿2,383
฿2,628 total
includes taxes & fees
5 Oct - 6 Oct
Travelodge by Wyndham Winchester
A gym with treadmills, exercise balls, and a mirrored wall.

14. 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 ฿3,136
฿3,553 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn Winchester-University/Mall Area
A restaurant interior with a bar area, seating, and artwork on the walls.

15. 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, (1,000 reviews)
"Always a great stay when golfing at Blue Ridge Shadows!"
United States
Brian
The price is ฿3,908
฿4,310 total
includes taxes & fees
1 Nov - 2 Nov
DoubleTree by Hilton Front Royal Blue Ridge Shadows
A hotel lobby with a reception desk, seating area with a round table, and a bar.

16. 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 ฿3,794
฿4,223 total
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites Strasburg Shenandoah Valley
An outdoor seating area with a fire feature, wicker furniture, and a building with multiple windows.

17. 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, (606 reviews)
"Had an absolute great stay."
United States
Justin
The price is ฿4,665
฿5,212 total
includes taxes & fees
20 Oct - 21 Oct
TownePlace Suites by Marriott Front Royal
A spacious living room with a fireplace, wooden staircase, and a bookshelf.

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, (1,003 reviews)
"Great stay."
United States
Allen
The price is ฿3,010
฿3,350 total
includes taxes & fees
25 Oct - 26 Oct
Country Inn & Suites by Radisson, Winchester, VA
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, (1,004 reviews)
"It was our third time staying here—always such a great place to stay. The staff is the friendliest!"
United States
Joseph
The price is ฿2,824
฿3,143 total
includes taxes & fees
25 Oct - 26 Oct
Quality Inn Winchester
A modern interior with a geometric ceiling design, recessed lighting, and hanging pendant lights.

20. 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 ฿3,908
฿4,427 total
includes taxes & fees
12 Oct - 13 Oct
Hilton Garden Inn 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 for the activities you enjoy most. Learn more about Old Town Winchester
Learn more about Old Town Winchester
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 nice stay and the staff was very friendly. We will probably visit again."
Kira 1-night trip
Posted 14 hours ago
The Inn at Charles Town - Hollywood Casino

Frequently asked questions

What is Old Town Winchester like?
Old Town Winchester is an historic neighbourhood known for its array of dining options. Are you looking for Old Town Winchester travel tips? Make sure that you visit Bright Box Theater and Shenandoah Valley Discovery Museum while you're in the neighbourhood.
Where is the best place to stay in Old Town Winchester?
Based on our traveller 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 should I expect to find in the Old Town Winchester area?
With 13 Expedia hotels and other accommodation options 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, the majority of room reservations are fully refundable provided that you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within 24 hours of your booking. Enter dates in and click on "Search", then use the filter option "fully refundable" to review the best deals available in Old Town Winchester.
What is there to do around this Winchester neighbourhood?
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 worth a visit in the neighbourhood. 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.