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May 10 - May 11
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May 11 - May 12
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May 15 - May 17
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May 22 - May 24

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Our top choices for Old Town Winchester hotels

Bar (on property)

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, (1,009 reviews)
" Try nice hotel and a great location. "
United States
Steven
The price is ￥19,143
￥21,690 total
includes taxes & fees
Jun 11 - Jun 12
The George Washington Hotel, A Wyndham Grand Hotel
Lobby

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park
2.0 star property
30.4 km from Old Town Winchester
7.6 out of 10, Good, (1,006 reviews)
"Location is right across the road from Spelunker's, the best casual restaurant in Virginia."
United States
Rachel
The price is ￥11,438
￥12,731 total
includes taxes & fees
May 12 - May 13
Super 8 by Wyndham Front Royal Near Shenandoah National Park
Lobby

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
2 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,034 reviews)
"Great location, clean rooms and friendly staff."
United States
Daniel
The price is ￥12,982
￥14,709 total
includes taxes & fees
May 31 - Jun 1
Spark by Hilton Winchester
Garden

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
14.1 km from Old Town Winchester
9.6 out of 10, Exceptional, (176 reviews)
"Everything about this special place is incredible."
United States
James
The price is ￥33,702
￥37,173 total
includes taxes & fees
May 12 - May 13
L'Auberge Provencale Inn & Restaurant
Front of property

Hillbrook Inn

Hillbrook Inn
4.0 star property
21.7 km from Old Town Winchester
8.6 out of 10, Excellent, (677 reviews)
"Wonderful staff, and fall cottage was lovely."
United States
Henrik
The price is ￥24,912
￥31,819 total
includes taxes & fees
May 12 - May 13
Hillbrook Inn
Indoor pool

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
25 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,007 reviews)
"Friendly staff clean and comfy"
United Kingdom
Helen
The price is ￥19,206
￥21,377 total
includes taxes & fees
May 31 - Jun 1
Hampton Inn Front Royal
Porch

Relax Inn Motel

Relax Inn Motel
2.0 star property
27.6 km from Old Town Winchester
8.2 out of 10, Very Good, (273 reviews)
"On my way back from shenendoah and Luray to dc place was fine "
United States
tara
The price is ￥10,184
￥11,336 total
includes taxes & fees
May 12 - May 13
Relax Inn Motel
Room, 1 King Bed, Non Smoking | Premium bedding, pillowtop beds, blackout drapes, iron/ironing board

Travelodge By Wyndham Charles Town/Harpers Ferry

Travelodge By Wyndham Charles Town/Harpers Ferry
2.0 star property
29.5 km from Old Town Winchester
7.0 out of 10, Good, (279 reviews)
"Basic accommodations, clean room, friendly staff, decent continental breakfast options. Overall, a very nice stay for the price range. "
United States
Kevin
The price is ￥9,988
￥11,286 total
includes taxes & fees
May 12 - May 13
Travelodge By Wyndham Charles Town/Harpers Ferry
Exterior

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, (1,110 reviews)
"Very friendly front desk Quiet surroundings. Great restaurant nearby"
United States
Rosemary
The price is ￥16,903
￥18,390 total
includes taxes & fees
May 17 - May 18
Comfort Inn & Suites Winchester
Exterior

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, (974 reviews)
"Beautiful hotel!"
United States
David
The price is ￥16,765
￥18,240 total
includes taxes & fees
May 19 - May 20
Courtyard by Marriott Winchester
Property amenity

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, (576 reviews)
"Clean"
United States
Padmanabhan
The price is ￥19,898
￥22,261 total
includes taxes & fees
May 17 - May 18
TownePlace Suites by Marriott Front Royal
Restaurant

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, (572 reviews)
"Very friendly staff in a great location and well maintained. Convenient shuttle to the casino. Staff was exceptionally friendly and helpful"
United States
Kevin
The price is ￥15,341
￥18,748 total
includes taxes & fees
May 13 - May 14
The Inn at Charles Town - Hollywood Casino
Lobby

Days Inn by Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry
2.0 star property
29.6 km from Old Town Winchester
8.0 out of 10, Very Good, (1,006 reviews)
"Definitely stay somewhere else"
United States
William
The price is ￥11,713
￥13,235 total
includes taxes & fees
Jun 4 - Jun 5
Days Inn by Wyndham Charles Town/Harpers Ferry
Dining

Wayside Inn

Wayside Inn
3.5 star property
19.8 km from Old Town Winchester
9.2 out of 10, Wonderful, (430 reviews)
"Old building but clean and very comfortable. Perfect spot and price."
United States
Caroline
The price is ￥19,037
￥22,562 total
includes taxes & fees
May 12 - May 13
Wayside Inn
Front of property

The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
29.3 km from Old Town Winchester
9.6 out of 10, Exceptional, (447 reviews)
"Lovely inn with gracious hosts and fabulous breakfast. "
United States
Megan
The price is ￥23,493
￥26,547 total
includes taxes & fees
Jun 1 - Jun 2
The Carriage Inn B&B
Exterior

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, (888 reviews)
"Location was excellent"
United States
Jennie
The price is ￥16,831
￥19,069 total
includes taxes & fees
May 24 - May 25
Hampton Inn Winchester N/Conference Center, VA
Free daily buffet breakfast

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, (2,282 reviews)
"Hotel was clean, staff were attentive and breakfast was good."
Canada
Sandra
The price is ￥18,606
￥20,244 total
includes taxes & fees
May 18 - May 19
La Quinta Inn & Suites by Wyndham Winchester
Snack bar

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
4.4 km from Old Town Winchester
9.0 out of 10, Wonderful, (846 reviews)
"I'd vouch for them as if it was my Hotel, Very nice place to stay."
United States
Jhoan
The price is ￥19,748
￥21,486 total
includes taxes & fees
May 17 - May 18
TRU By Hilton Winchester
Exterior

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
4.3 km from Old Town Winchester
9.2 out of 10, Wonderful, (1,006 reviews)
"Great breakfast. Very clean. Parking was safe and easy. Staff was excellent!"
United States
Diane
The price is ￥13,937
￥15,163 total
includes taxes & fees
May 24 - May 25
Quality Inn Winchester
2 bars/lounges, sports bar

Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town
2.0 star property
29.7 km from Old Town Winchester
8.6 out of 10, Excellent, (1,007 reviews)
"Clean room, friendly staff. Fair breakfast…the bagels and muffins were old."
United States
Barbara
The price is ￥11,984
￥13,542 total
includes taxes & fees
May 26 - May 27
Rodeway Inn & Suites Charles Town
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.
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

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows

10/10 Excellent
"Perfect!"
Mark 2-night trip
Posted 1 hour ago
DoubleTree by Hilton Front Royal Blue Ridge Shadows

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.