Old Town Winchester Travel Guide
Tourist Guide
Visit Old Town Winchester
Stay near popular Old Town Winchester attractions
Our pick of the best Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is NZ$245 per night from 26 July to 27 July
NZ$245
26 July - 27 July
includes taxes & fees
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 clean rooms ...
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 27 June 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is NZ$174 per night from 26 July to 27 July
NZ$174
26 July - 27 July
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking and a fitness centre. Our guests praise the helpful staff and the clean ...
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 24 June 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is NZ$166 per night from 5 July to 6 July
NZ$166
5 July - 6 July
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their 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 26 June 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is NZ$185 per night from 1 July to 2 July
NZ$185
1 July - 2 July
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,003 reviews)
"Staff very friendly, good and clean facility. Good restaurants near by. Will stay again."
Reviewed on 27 June 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
The price is NZ$166 per night from 8 July to 9 July
NZ$166
8 July - 9 July
includes taxes & fees
Stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
8.2/10 Very good! (1,005 reviews)
"The hotel was good and room was clean. Breakfast was ok"
Reviewed on 25 June 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is NZ$182 per night from 26 July to 27 July
NZ$182
26 July - 27 July
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (1,442 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 27 June 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.
Our guide on where to stay in Old Town Winchester
Find the best Old Town Winchester areas 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.
