Old Town Winchester, VA
Winchester
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Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is ￥21,088 per night from Jul 21 to Jul 22
￥21,088
￥23,893 total
Jul 21 - Jul 22
includes taxes & fees
Book a stay at this spa hotel in Winchester. Enjoy a full-service spa, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9.4/10 Exceptional! (1,008 reviews)
"This was the neatest place I've stayed at. The building is gorgeous and they've kept the historic aspects of it very nice. Beds were very comfortable. Shower was hot and had good pressure. Staff was all very friendly. There's a nice pub with live music right next door. Lots to do and see in this ..."
Reviewed on Jun 27, 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is ￥13,992 per night from Jul 26 to Jul 27
￥13,992
￥15,852 total
Jul 26 - Jul 27
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and ...
9/10 Wonderful! (1,010 reviews)
"This newly renovated, squeaky clean hotel is a favorite of ours as a stop off on our I-81 journeys. It is at an excellent location, quiet, clean, and the rooms are spacious. Hotel gym, breakfast, and pool are excellent additions to our stay here. They are also pet friendly and have a nice spot to ..."
Reviewed on Jun 28, 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is ￥13,726 per night from Jul 5 to Jul 6
￥13,726
￥15,141 total
Jul 5 - Jul 6
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (988 reviews)
"Great overnight stay with the family. The rooms were clean and comfortable, and the kids absolutely loved the breakfast spread. I would recommend staying here if you're in the area or just passing through."
Reviewed on Jun 26, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is ￥15,042 per night from Jul 6 to Jul 7
￥15,042
￥16,852 total
Jul 6 - Jul 7
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9.2/10 Wonderful! (1,005 reviews)
"Clean. Friendly staff. Zero complaints."
Reviewed on Jun 28, 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
The price is ￥13,828 per night from Jul 5 to Jul 6
￥13,828
￥15,390 total
Jul 5 - Jul 6
includes taxes & fees
Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,007 reviews)
"Not impressed. Some weird stains on the mattress cover and beside the bed. Sheets were clean. Bed was comfy. Dirty sink. Stained shower curtain and bedspread. Checking in, staff was great. Day staff was not nice and barely spoke. Lady running breakfast was very rude when someone told her the coffee ..."
Reviewed on Jun 27, 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is ￥15,915 per night from Jul 2 to Jul 3
￥15,915
￥17,316 total
Jul 2 - Jul 3
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,443 reviews)
"The room was comfortable, the water pressure was good in the shower, the air conditioning was good, and the bed was good. I would stay again."
Reviewed on Jun 27, 2026
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 Winchester Little Theater.
