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$235 per night from 23 Aug to 24 Aug
NZ$235
23 Aug - 24 Aug
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 ...
Nostalgia Lane in the heart of the city
Winchester VA
The price is NZ$554 per night from 16 Aug to 17 Aug
NZ$554
16 Aug - 17 Aug
includes taxes & fees
Stay at this apartment in Winchester. Enjoy laundry facilities, an in-room coffee maker and air conditioning. Popular attractions Bright Box Theater and Old ...
9.2/10 Wonderful! (18 reviews)
"Perfect location for exploring Winchester. Beautiful rooms. Clean and comfortable."
Reviewed on 27 July 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is NZ$150 per night from 2 Sept to 3 Sept
NZ$150
2 Sept - 3 Sept
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 ...
9.2/10 Wonderful! (1,004 reviews)
"Large size room, very clean! Personal hand written greeting from manager was a great touch in today's world!"
Reviewed on 13 Aug 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is NZ$181 per night from 23 Aug to 24 Aug
NZ$181
23 Aug - 24 Aug
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 ...
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is NZ$185 per night from 16 Aug to 17 Aug
NZ$185
16 Aug - 17 Aug
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (2,263 reviews)
"This hotel was full of ants. I booked my hotel through Expedia Hotels.com, and now I have to do all the footwork to get reimbursed for my food that was in sealed bags wrapped up that was completely invaded by aunt. All of my clothing had ants in it. my bed had ants in it. There was four different ..."
Reviewed on 15 Aug 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
The price is NZ$153 per night from 23 Aug to 24 Aug
NZ$153
23 Aug - 24 Aug
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 ...
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 Shenandoah Valley Discovery Museum and Stonewall Jackson's Headquarters.
