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Our top choices for Old Town Winchester hotels

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, (1,005 reviews)
"The staff was helpful and kind. The architecture was incredible."
United States
Allison
The price is ₩207,542
₩235,144 total
includes taxes & fees
May 24 - May 25
The George Washington Hotel, A Wyndham Grand Hotel

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
2 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,015 reviews)
"Great location, clean rooms and friendly staff."
United States
Daniel
The price is ₩124,943
₩141,561 total
includes taxes & fees
Jun 8 - Jun 9
Spark by Hilton Winchester

Hampton Inn Front Royal

Hampton Inn Front Royal
2.5 star property
25 km from Old Town Winchester
9.0 out of 10, Wonderful, (1,012 reviews)
"I enjoyed my stay. The room was clean and the breakfast was varied."
United States
Brenda
The price is ₩189,675
₩211,108 total
includes taxes & fees
May 31 - Jun 1
Hampton Inn Front Royal

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, (1,009 reviews)
"Location is right across the road from Spelunker's, the best casual restaurant in Virginia."
United States
Rachel
The price is ₩103,336
₩115,018 total
includes taxes & fees
May 18 - May 19
Super 8 by Wyndham Front Royal Near Shenandoah National Park

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 ₩322,141
₩355,322 total
includes taxes & fees
May 25 - May 26
L'Auberge Provencale Inn & Restaurant

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, (1,099 reviews)
"Very friendly front desk Quiet surroundings. Great restaurant nearby"
United States
Rosemary
The price is ₩160,591
₩174,723 total
includes taxes & fees
Jun 10 - Jun 11
Comfort Inn & Suites Winchester

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, (280 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 ₩95,474
₩107,885 total
includes taxes & fees
May 18 - May 19
Travelodge By Wyndham Charles Town/Harpers Ferry

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 ₩238,123
₩304,140 total
includes taxes & fees
May 21 - May 22
Hillbrook Inn

Relax Inn Motel

Relax Inn Motel
2.0 star property
27.6 km from Old Town Winchester
8.2 out of 10, Very Good, (274 reviews)
"The owners/managers are delightful. The room was very nice with excellent bedding. I look forward to staying there again "
United States
Sarah
The price is ₩97,346
₩108,354 total
includes taxes & fees
May 19 - May 20
Relax Inn Motel

Wayside Inn

Wayside Inn
3.5 star property
19.8 km from Old Town Winchester
9.2 out of 10, Wonderful, (431 reviews)
"Cozy and quaint. Felt like being in a home filled with lots of history! The people were very friendly in the restaurant and bar. Would definitely stay again. "
United States
Kelly
The price is ₩181,962
₩215,665 total
includes taxes & fees
May 18 - May 19
Wayside Inn

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, (1,004 reviews)
"Best breakfast week had all week at a hotel. Friendly staff & clean rooms."
United States
Lauren
The price is ₩110,630
₩125,012 total
includes taxes & fees
Jun 2 - Jun 3
Days Inn by Wyndham Charles Town/Harpers Ferry

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, (977 reviews)
"Beautiful hotel!"
United States
David
The price is ₩160,246
₩174,348 total
includes taxes & fees
Jun 4 - Jun 5
Courtyard by Marriott Winchester

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, (889 reviews)
"Location was excellent"
United States
Jennie
The price is ₩160,875
₩182,272 total
includes taxes & fees
May 24 - May 25
Hampton Inn Winchester N/Conference Center, VA

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, (857 reviews)
"The hotel is a little dated, but very clean. Breakfast had a good selection. "
United States
Deborah
The price is ₩157,251
₩171,090 total
includes taxes & fees
May 31 - Jun 1
Holiday Inn Express Winchester South-Stephens City by IHG

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, (860 reviews)
"I'd vouch for them as if it was my Hotel, Very nice place to stay."
United States
Jhoan
The price is ₩177,739
₩193,374 total
includes taxes & fees
May 24 - May 25
TRU By Hilton Winchester

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, (576 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 ₩152,743
₩186,050 total
includes taxes & fees
May 27 - May 28
The Inn at Charles Town - Hollywood Casino

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley
2.5 star property
25.8 km from Old Town Winchester
8.4 out of 10, Very Good, (1,006 reviews)
"Nice stay no issues, and front desk person very pleasant."
United Kingdom
William
The price is ₩124,753
₩138,850 total
includes taxes & fees
May 31 - Jun 1
Ramada by Wyndham Strasburg/Shenandoah Valley

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 ₩252,320
₩285,121 total
includes taxes & fees
Jun 1 - Jun 2
The Carriage Inn B&B

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, (1,459 reviews)
"This was my first stay at a Microtel and i was very impressed wirh the design and how well sound was controlled. I'll definitely stay again. "
United States
Carol
The price is ₩142,574
₩155,109 total
includes taxes & fees
May 18 - May 19
Microtel Inn & Suites by Wyndham Winchester

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, (577 reviews)
"Great location to explore the Shenandoah mountains . Lots of shops and eateries."
United States
katherine
The price is ₩190,199
₩212,784 total
includes taxes & fees
Jun 7 - Jun 8
TownePlace Suites by Marriott Front Royal
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.

Where to stay in Old Town Winchester

Find the best Old Town Winchester areas and neighborhoods for the activities you enjoy most.

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

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 George Washington's Office are some other stops to visit in the neighborhood. A few places to visit in the area around Old Town Winchester include Handley Regional Library, 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.