Old Town Winchester Travel Guide

Winchester

The Courthouse in Winchester, Virginia.
Old Town Winchester
Old Town Winchester
Old Town Winchester
Old Town Winchester

Popular places to visit


Top hotels in Old Town Winchester

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
The price is ฿4,298 per night from 7 Jul to 8 Jul
฿4,298
฿4,870 total
7 Jul - 8 Jul
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! (1,004 reviews)
"This place was perfect! Close to old town, clean, helpful, we were so pleased with our stay!"

Reviewed on 18 Jun 2026

The George Washington Hotel, A Wyndham Grand Hotel
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is ฿3,250 per night from 28 Jun to 29 Jun
฿3,250
฿3,682 total
28 Jun - 29 Jun
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! (1,007 reviews)
"Quick & easy."

Reviewed on 19 Jun 2026

Spark by Hilton Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
The price is ฿2,548 per night from 5 Jul to 6 Jul
฿2,548
฿2,810 total
5 Jul - 6 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! (971 reviews)
"Five stars throughout the hotel ,nice place"

Reviewed on 20 Jun 2026

TRU By Hilton Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
The price is ฿2,341 per night from 21 Jun to 22 Jun
฿2,341
฿2,547 total
21 Jun - 22 Jun
includes taxes & fees
Stay at this motel in Winchester. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8.6/10 Excellent! (1,049 reviews)
"Tidy, well-run, and convenient. I'd stay there again."

Reviewed on 19 Jun 2026

Travelodge by Wyndham Winchester
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr Strasburg VA
The price is ฿2,662 per night from 19 Jul to 20 Jul
฿2,662
฿2,963 total
19 Jul - 20 Jul
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 staff was very friendly. We arrived and checked in with no problems. My husband asked the manager if he could park our show bike under the canapé to ensure it was safe and they said yes. The breakfast was your typical motel breakfast. We did I not use the pool or gym but they looked clean."

Reviewed on 20 Jun 2026

Ramada by Wyndham Strasburg/Shenandoah Valley
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
The price is ฿3,165 per night from 6 Jul to 7 Jul
฿3,165
฿3,443 total
6 Jul - 7 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! (1,451 reviews)
"All was excellent. I will definitely stay again"

Reviewed on 19 Jun 2026

Microtel Inn & Suites by Wyndham Winchester
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

Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Winchester Little Theater.



Old Town Winchester Travel Guide