Old Town Winchester Travel Guide
Winchester
Visit Old Town Winchester
Stay near popular Old Town Winchester attractions
Top hotels in Old Town Winchester
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
The price is ฿4,045 per night from 27 Aug to 28 Aug
฿4,045
฿4,583 total
27 Aug - 28 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 ...
9.4/10 Exceptional! (1,001 reviews)
"Clean room, plenty of fresh towels, staff friendly but could have greeted with more information as to what was offered at hotel."
Reviewed on 12 Aug 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is ฿2,560 per night from 2 Sept to 3 Sept
฿2,560
฿2,900 total
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 ฿3,086 per night from 23 Aug to 24 Aug
฿3,086
฿3,534 total
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 ...
9/10 Wonderful! (1,001 reviews)
"I would give it a 5 star rating but just a few things. Staff and lobby were excellent. Breakfast was terrific. Great coffee. Room was nice. AC a little noisy and the bathroom had a few rusty screws, horrible caulk job on the bath faucet and a big stain in the tub. Will definately go back."
Reviewed on 13 Aug 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
The price is ฿3,575 per night from 6 Sept to 7 Sept
฿3,575
฿3,979 total
6 Sept - 7 Sept
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! (2,260 reviews)
"Amazing stay. The front desk woman was so kind when we walked in!! It was much appreciated after a long day of traveling. Clean room, excellent coffee in the morning and just a really nice stay."
Reviewed on 13 Aug 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
The price is ฿2,673 per night from 24 Aug to 25 Aug
฿2,673
฿2,975 total
24 Aug - 25 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 ...
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is ฿2,920 per night from 30 Aug to 31 Aug
฿2,920
฿3,250 total
30 Aug - 31 Aug
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! (1,430 reviews)
"You could hear the people above you."
Reviewed on 12 Aug 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.
Where to stay in Old Town Winchester
Find the best Old Town Winchester areas for the activities you enjoy most. Learn more about Old Town Winchester
Learn more about Old Town Winchester
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 Stonewall Jackson's Headquarters.
