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 ฿4,341 per night from 10 Aug to 11 Aug
฿4,341
฿4,918 total
10 Aug - 11 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! (1,015 reviews)
"Very good restaurant and staff. Highly recommend This hotel it's very old but up to date,large well furnished rooms and great bed."
Reviewed on 8 Jul 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
The price is ฿2,730 per night from 30 Jul to 31 Jul
฿2,730
฿3,039 total
30 Jul - 31 Jul
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! (1,026 reviews)
"Everything was great except for the fact the shower was terrible. It felt like it took me an hour just to rinse the sham out of my hair because the water was coming out in a slow trickle. It was so bad I thought I would have to just rinse my head under the sink!"
Reviewed on 10 Jul 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
The price is ฿2,322 per night from 30 Jul to 31 Jul
฿2,322
฿2,631 total
30 Jul - 31 Jul
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! (1,010 reviews)
"Great staff, clean rooms and delightful breakfast. I'll be back!"
Reviewed on 5 Jul 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
The price is ฿2,765 per night from 2 Aug to 3 Aug
฿2,765
฿3,178 total
2 Aug - 3 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! (1,014 reviews)
"This is a beautiful B&B. Perfect location & very helpful staff. I highly recommend it."
Reviewed on 10 Jul 2026
Ramada by Wyndham Strasburg/Shenandoah Valley
21 Signal Knob Dr Strasburg VA
The price is ฿2,745 per night from 2 Aug to 3 Aug
฿2,745
฿3,055 total
2 Aug - 3 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 ...
8.2/10 Very good! (1,011 reviews)
"The room was hot and blankets were damp. The TV didn’t work, staff was not helpful. After they changed the room it wasn’t better. The fire alarm went off at 10:28pm, frantic my kids and I got ready to evacuate. The alarm stopped before we could exit and the staff said they were testing the alarm!!! ..."
Reviewed on 11 Jul 2026
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
The price is ฿3,116 per night from 22 Jul to 23 Jul
฿3,116
฿3,468 total
22 Jul - 23 Jul
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! (1,436 reviews)
"Great spot! Been there more than twice!"
Reviewed on 10 Jul 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 Winchester Little Theater.
