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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)
"Always great place and the old nostalgic look is the best"
United States
Christophe
The price is ￥20,831
￥23,601 total
includes taxes & fees
Nov 22 - Nov 23
The George Washington Hotel, A Wyndham Grand Hotel
A modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.

2. 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, (1,438 reviews)
"Perfect accommodation- great breakfast and attentive gracious staff"
United States
Kathleen
The price is ￥12,654
￥14,084 total
includes taxes & fees
Nov 15 - Nov 16
Microtel Inn & Suites by Wyndham Winchester
A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.

3. 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, (2,268 reviews)
"Great place to stay the night after a long drive"
United States
lucy
The price is ￥14,803
￥16,475 total
includes taxes & fees
Nov 29 - Nov 30
La Quinta Inn & Suites by Wyndham Winchester
A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.

4. 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)
"Great hotel."
United States
Nicholas
The price is ￥15,817
￥18,083 total
includes taxes & fees
Dec 13 - Dec 14
Holiday Inn Winchester Se-Historic Gateway by IHG
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, (1,002 reviews)
"Clean room, great staff, good parking and free breakfast"
United States
Albert
The price is ￥10,388
￥11,770 total
includes taxes & fees
Nov 29 - Nov 30
Spark by Hilton Winchester
A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.

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, (975 reviews)
"Great place to stay in Winchester."
United States
Thomas
The price is ￥14,803
￥16,476 total
includes taxes & fees
Nov 16 - Nov 17
Fairfield Inn & Suites by Marriott Winchester
A Courtyard by Marriott hotel with a covered entrance, multiple floors, and a brick facade.

7. 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)
"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 ￥17,111
￥19,045 total
includes taxes & fees
Nov 22 - Nov 23
Courtyard by Marriott Winchester
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, (1,000 reviews)
"Rooms good sized, beds comfortable, quiet ( slept great), great breakfast. Highly recommend!!"
United States
Jesse
The price is ￥12,970
￥14,435 total
includes taxes & fees
Nov 22 - Nov 23
TRU By Hilton Winchester
A modern hotel lobby with a central dining area, a reception desk, and a large window providing natural light.

9. 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, (964 reviews)
"The breakfast was delicious, it was very welcoming very clean best ever had at motel"
United States
Elizabeth
The price is ￥16,900
￥19,147 total
includes taxes & fees
Nov 20 - Nov 21
Hampton Inn Winchester N/Conference Center, VA
A buffet with multiple self-service stations, including omelets and other prepared foods.

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, (871 reviews)
"Very clean comfortable bed good breakfast"
United States
David
The price is ￥17,428
￥19,397 total
includes taxes & fees
Dec 13 - Dec 14
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, (1,153 reviews)
"Convenient to the highway and reasonably priced."
United States
Donna S.
The price is ￥14,803
￥16,475 total
includes taxes & fees
Nov 22 - Nov 23
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, (915 reviews)
"Great place to stay"
United States
Roy
The price is ￥18,137
￥20,188 total
includes taxes & fees
Nov 22 - Nov 23
SpringHill Suites by Marriott Winchester
A restaurant interior with a bar area, seating, and artwork on the walls.

13. 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)
"It was a nice stay.. third time staying… relaxing and peaceful"
United States
Adrian
The price is ￥18,727
￥20,656 total
includes taxes & fees
Dec 13 - Dec 14
DoubleTree by Hilton Front Royal Blue Ridge Shadows
A spacious living room with a fireplace, wooden staircase, and a bookshelf.

14. 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)
"Comfortable bed, friendly staff, and convenient location"
United States
Zohair
The price is ￥13,791
￥15,349 total
includes taxes & fees
Dec 6 - Dec 7
Country Inn & Suites by Radisson, Winchester, VA
An outdoor seating area with a fire feature, wicker furniture, and a building with multiple windows.

15. 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, (619 reviews)
"Cleaned, maintained hotel near many conveniences."
United States
JoEllen
The price is ￥21,569
￥24,110 total
includes taxes & fees
Nov 17 - Nov 18
TownePlace Suites by Marriott Front Royal
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 clean room and property. Staff was great. Breakfast was good."
United States
Kayla
The price is ￥19,268
￥21,445 total
includes taxes & fees
Nov 22 - Nov 23
Fairfield Inn & Suites Strasburg Shenandoah Valley
A spacious dining area with round tables and chairs, a large potted plant, and a wall with artwork.

17. 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, (660 reviews)
"The staff and place were great, with a shuttle running back and forth to the casino."
United States
HARRY
The price is ￥15,643
￥19,119 total
includes taxes & fees
Nov 30 - Dec 1
The Inn at Charles Town - Hollywood Casino
A hotel room with a bed, a chair, a desk, a lamp, and a picture on the wall.

18. 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, (562 reviews)
"Great location."
United States
Mark
The price is ￥18,877
￥21,388 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Garden Inn Winchester
A snack and beverage display area with shelves stocked with various snacks and a refrigerated section with beverages.

19. 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 ￥14,678
￥16,631 total
includes taxes & fees
Dec 6 - Dec 7
Hampton Inn Winchester-University/Mall Area
A modern hotel lobby with a green sofa, blue chairs, a dining table, and large windows offering a view of the outdoors.

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, (926 reviews)
"Great hotel"
United States
Michael
The price is ￥12,471
￥13,880 total
includes taxes & fees
Dec 11 - Dec 12
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.
View all properties

Compare popular hotels in Old Town Winchester

Property
Star rating
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
1,003 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
1,002 reviews
View
A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.
Fairfield Inn & Suites by Marriott Winchester
3.0 star property
9.2
Wonderful
975 reviews
View
A hotel room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.
Quality Inn Winchester
2.5 star property
9.4
Exceptional
1,004 reviews
View
A modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.
Microtel Inn & Suites by Wyndham Winchester
2.5 star property
9.2
Wonderful
1,438 reviews
View

Hotels recommended for families in Old Town Winchester

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

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)
The price is ￥20,831
￥23,601 total
includes taxes & fees
Nov 22 - Nov 23
The George Washington Hotel, A Wyndham Grand Hotel

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

A courtyard with a fountain, tables with white tablecloths, and brick buildings.
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
Old Town Winchester

10/10 Excellent

It was a beautiful place to stay, loved the pool and hot tub! My room was the junior suite with a jacuzzi and it was absolutely luxurious!
United States
Kelley Ann
Reviewed May 31, 2023
The George Washington Hotel, A Wyndham Grand Hotel

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.