Old Town Winchester, VA
Winchester
Visit Old Town Winchester
Stay near popular Old Town Winchester attractions
Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is NT$4,275 per night from Jun 28 to Jun 29
NT$4,275
NT$4,844 total
Jun 28 - Jun 29
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! (1,006 reviews)
"Beautiful building located in the heart of the historic district. The rooms were well-appointed, with comfortable bedding/pillows, a fireplace, and a multi-jet shower and jacuzzi tub where we stayed. There was a very good musical act performing in the hotel bar when we checked in Friday night and ..."
Reviewed on 2026/6/27
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is NT$2,758 per night from Jul 23 to Jul 24
NT$2,758
NT$3,125 total
Jul 23 - Jul 24
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! (1,009 reviews)
"Overall great experience - with that said their computer system wasnt working right. I was charged for the room twice (over and above the already charged payment from Expedia) and also a $100 security deposit. I brought it up the next day and it was immediately corrected. Nice hotel, good local, ..."
Reviewed on 2026/6/24
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is NT$2,705 per night from Jul 5 to Jul 6
NT$2,705
NT$2,984 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 2026/6/26
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is NT$2,965 per night from Jul 6 to Jul 7
NT$2,965
NT$3,321 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 ...
9/10 Wonderful! (1,002 reviews)
"Staff very friendly, good and clean facility. Good restaurants near by. Will stay again."
Reviewed on 2026/6/27
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
The price is NT$2,726 per night from Jun 28 to Jun 29
NT$2,726
NT$3,034 total
Jun 28 - Jun 29
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! (1,005 reviews)
"The hotel was good and room was clean. Breakfast was ok"
Reviewed on 2026/6/25
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is NT$3,188 per night from Jul 23 to Jul 24
NT$3,188
NT$3,468 total
Jul 23 - Jul 24
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! (1,441 reviews)
"Mostly shower, water pressure"
Reviewed on 2026/6/27
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.
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.
