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Discover 322 Old Town Winchester hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Exterior
La Quinta Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (1351)
"Love this hotel. Very clean and fancy for the price. Bed is very comfortable and the layout of the rooms are nice. "
The price is $116
$126 total
includes taxes & fees
Jun 2 - Jun 3
La Quinta Inn & Suites by Wyndham Winchester
Seasonal outdoor pool
Travelodge by Wyndham Winchester
2.5 star property
8.0 out of 10, Very Good, (1068)
"The room was very good. The breakfast was mediocre."
The price is $70
$76 total
includes taxes & fees
Jun 9 - Jun 10
Travelodge by Wyndham Winchester
Premium bedding, pillowtop beds, desk, blackout drapes
Days Inn by Wyndham Charles Town/Harpers Ferry
2.0 star property
8.2 out of 10, Very Good, (908)
"Room is really clean. Was nervous when drove up property bc it seems outdated."
The price is $65
$73 total
includes taxes & fees
Jun 24 - Jun 25
Days Inn by Wyndham Charles Town/Harpers Ferry
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Lobby
Microtel Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (783)
"Our room up on the 4th floor is nice and clean. But the bathroom exhaust fan is so loud we just turn off the lights and kept door open. It was just so annoying and loud. Highway noise also can be heard all times although the drape when closed helped to reduce the noise. Ask for room away from highway if you stay here. Other wise, this hotel is recommended. "
The price is $84
$92 total
includes taxes & fees
Jun 2 - Jun 3
Microtel Inn & Suites by Wyndham Winchester
Exterior
The Inn at Charles Town
3.0 star property
8.4 out of 10, Very Good, (336)
"The Inn was everything we needed. Front Desk Team was very polite and helpful. Shuttle driver was friendly and the shuttle was timely. The breakfast was "continental" but offered many options. I would definitely stay again."
The price is $97
$119 total
includes taxes & fees
May 28 - May 29
The Inn at Charles Town
Bar (on property)
The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
9.4 out of 10, Exceptional, (1004)
"Beautiful town. The hotel is beautiful. "
The price is $125
$142 total
includes taxes & fees
May 28 - May 29
The George Washington Hotel, A Wyndham Grand Hotel
Lobby
Sleep Inn & Suites
2.5 star property
8.2 out of 10, Very Good, (1004)
"Nice "
The price is $81
$88 total
includes taxes & fees
Jun 24 - Jun 25
Sleep Inn & Suites
Exterior
Comfort Inn & Suites
2.5 star property
9.4 out of 10, Exceptional, (939)
"New clean and sharp!!!"
The price is $101
$110 total
includes taxes & fees
Jun 2 - Jun 3
Comfort Inn & Suites
Exterior
Holiday Inn Winchester Se-Historic Gateway, an IHG Hotel
3.0 star property
9.0 out of 10, Wonderful, (1001)
"Very clean love Holiday Inn"
The price is $110
$123 total
includes taxes & fees
Jun 2 - Jun 3
Holiday Inn Winchester Se-Historic Gateway, an IHG Hotel
Superior Room, 1 King Bed, Non Smoking | Desk, blackout drapes, free cribs/infant beds, free WiFi
Red Roof Inn Winchester, VA
2.0 star property
7.4 out of 10, Good, (1005)
"Noisy guests in next door "
The price is $72
$78 total
includes taxes & fees
May 28 - May 29
Red Roof Inn Winchester, VA
Desk, laptop workspace, blackout drapes, iron/ironing board
Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
8.6 out of 10, Excellent, (1002)
"Very nice"
The price is $106
$116 total
includes taxes & fees
Jun 2 - Jun 3
Country Inn & Suites by Radisson, Winchester, VA
Terrace/patio
Home2 Suites by Hilton Charles Town
3.0 star property
9.8 out of 10, Exceptional, (617)
"Very pet friendly - clean - great staff. Definitely stay again. Also really cool racetrack casino 3 minutes away. "
The price is $152
$170 total
includes taxes & fees
Jun 9 - Jun 10
Home2 Suites by Hilton Charles Town
Lobby
Spark by Hilton Winchester
3.0 star property
9.0 out of 10, Wonderful, (1005)
"The rooms were large and very clean and comfortable!"
The price is $88
$99 total
includes taxes & fees
Jun 24 - Jun 25
Spark by Hilton Winchester
Hiking
Rodeway Inn & Suites - Charles Town, WV
2.0 star property
8.8 out of 10, Excellent, (800)
"Great."
The price is $72
$81 total
includes taxes & fees
Jun 16 - Jun 17
Rodeway Inn & Suites - Charles Town, WV
Exterior
Quality Inn
2.5 star property
8.8 out of 10, Excellent, (1000)
"Easy to find. Pleasant staff. Nice clean room"
The price is $93
$101 total
includes taxes & fees
Jun 9 - Jun 10
Quality Inn
Lobby
Hilton Garden Inn Martinsburg
3.0 star property
9.2 out of 10, Wonderful, (527)
"Room was clean Pillows were flat with no fluff - like why bother with a pillow at all! The breakfast was the worst ever! Choice of buffet or al la carte We opted for a la carte after seeing that the buffet was skimpy. Pancakes and waffles were like rubber - eggs were cold. Way understaffed - one girl waiting on all the tables I had to get my own syrup and I wound up toasting my own bread when she never came back. They ran out of coffee by 10 am and never made more even after we asked for more!...
The price is $110
$123 total
includes taxes & fees
Jun 9 - Jun 10
Hilton Garden Inn Martinsburg
Reception
Hampton Inn & Suites Charles Town
2.5 star property
9.4 out of 10, Exceptional, (1003)
"The hotel is near Charlestown casino and racetrack, but not close enough to have noises from the activity there bother us. We could see the track in the distance. The gym was adequate and the free morning breakfasts were great. During the week they even had brown bag snack packs you could take with fruit, Peanutbutter and jelly, small bagel and small bottle of water. That was an unexpected treat. "
The price is $139
$156 total
includes taxes & fees
Jun 11 - Jun 12
Hampton Inn & Suites Charles Town
Exterior
Fairfield Inn & Suites by Marriott Winchester
2.5 star property
8.8 out of 10, Excellent, (593)
"Close to highway, easy to find"
The price is $110
$119 total
includes taxes & fees
Jun 24 - Jun 25
Fairfield Inn & Suites by Marriott Winchester
Exterior
Motel 6 Charles Town, WV
2.0 star property
7.6 out of 10, Good, (626)
"Nice and clean rooms "
The price is $58
$65 total
includes taxes & fees
May 30 - May 31
Motel 6 Charles Town, WV
Free WiFi, bed sheets
Motel 6 Winchester, VA
2.0 star property
8.0 out of 10, Very Good, (1003)
"No frills, but clean and quiet overnight stay."
The price is $66
$75 total
includes taxes & fees
Jun 4 - Jun 5
Motel 6 Winchester, VA
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Old Town Winchester Travel Info

Number of reviews
17,542
Location
Winchester, United States of America
Accommodation
322 hotels
Known landmarks
Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theater
Hotels with nearby historical attractions
The George Washington Hotel, A Wyndham Grand Hotel, Red Roof Inn Winchester, VA and Hampton Inn Winchester N/Conference Center, VA
Known for
Cafes and history
Lowest price
$58
Highest price
$152

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 Shenandoah Valley Discovery Museum and Bright Box Theater while you're in the neighborhood.

Where is the best place to stay in Old Town Winchester?

Based on Expedia customer reviews, The George Washington Hotel, A Wyndham Grand Hotel is the highest ranked property 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?

Expedia has 7 Old Town Winchester hotels and other accommodations, and one might make a good home base for venturing out into 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.

Recent reviews of Old Town Winchester hotels