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 Rp2.582.617 per night from 4 Jun to 5 Jun
Rp2.582.617
Rp2.926.105 total
4 Jun - 5 Jun
includes taxes & fees
Stay at this spa hotel in Winchester. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
9.4/10 Exceptional! (1,007 reviews)
Toilets are low

Reviewed on 7 May 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
The price is Rp1.448.692 per night from 31 May to 1 Jun
Rp1.448.692
Rp1.641.435 total
31 May - 1 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! (1,028 reviews)
It was a nice hotel and very worth the price we paid! The Continental breakfast was great and had a lot of choices. The staff was very attentive as well.

Reviewed on 7 May 2026

Spark 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 Rp1.230.643 per night from 10 May to 11 May
Rp1.230.643
Rp1.338.974 total
10 May - 11 May
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! (1,059 reviews)
Air conditioning and heat worked properly, and easy to use. I like that the door to room has an alarm if door is left open. I love the big parking lot and design. Great for semi's, RV's, etc. Staff was so friendly and helpful at daytime front desk. I love the pull-down shades verses curtains. It ...

Reviewed on 8 May 2026

Travelodge by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike Winchester VA
The price is Rp1.663.968 per night from 24 May to 25 May
Rp1.663.968
Rp1.862.431 total
24 May - 25 May
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! (1,011 reviews)
Perfect hotel. I love this hotel.

Reviewed on 5 May 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
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 Rp1.650.102 per night from 10 May to 11 May
Rp1.650.102
Rp1.795.179 total
10 May - 11 May
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! (1,453 reviews)
Quiet. Very nice front desk lady gave us extra blankets when we asked. Great breakfast!

Reviewed on 6 May 2026

Microtel Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East Winchester VA
The price is Rp2.114.626 per night from 10 May to 11 May
Rp2.114.626
Rp2.300.782 total
10 May - 11 May
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! (2,280 reviews)
Breakfast was included, which is always a plus. Good was hot. Room was comfortable. Shower was amazing

Reviewed on 8 May 2026

La Quinta 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.

Other neighbourhoods around Old Town Winchester

Buildings and streets in the historic part of the ancient city of Winchester in Virginia.

Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.

Winchester Historic District


Old Town Winchester Travel Guide