Old Town Winchester Travel Guide

Winchester

Old Town Winchester
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby

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 3.296.760 ₫ per night from 31 Aug to 1 Sept
3.296.760 ₫
3.735.274 ₫ total
31 Aug - 1 Sept
includes taxes & fees
Stay at this 3.5-star spa hotel in Winchester. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the bar and the helpful staff in their ...
9.2/10 Wonderful! (1,008 reviews)
Super Getaway
"Great old hotel. Quiet, comfortable, beautiful. Staff were wonderful. Perfect location for walking around the downtown mall."

Reviewed on 23 Aug 2025

The George Washington Hotel, A Wyndham Grand Hotel
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 2.698.996 ₫ per night from 2 Sept to 3 Sept
2.698.996 ₫
2.936.539 ₫ total
2 Sept - 3 Sept
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (2,136 reviews)
"The bedroom was clean. Some area a bit older looking but good. Hall ways a little smelly like needs carpets refreshed. But not all that bad.."

Reviewed on 25 Aug 2025

La Quinta Inn & Suites 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 2.157.092 ₫ per night from 7 Sept to 8 Sept
2.157.092 ₫
2.425.939 ₫ total
7 Sept - 8 Sept
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,005 reviews)
"Clean and staff was great."

Reviewed on 23 Aug 2025

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
Fully refundableReserve now, pay when you stay
The price is 2.087.158 ₫ per night from 15 Sept to 16 Sept
2.087.158 ₫
2.270.829 ₫ total
15 Sept - 16 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 helpful staff and the clean rooms ...
9/10 Wonderful! (1,326 reviews)
"It was a great experiencia. It was really clean and the staff was exactly friendly and accommodated"

Reviewed on 24 Aug 2025

Microtel Inn & Suites by Wyndham Winchester
SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester

2.5 out of 5
280 MARKET STREET, Winchester, VA
The price is 2.822.406 ₫ per night from 1 Sept to 2 Sept
2.822.406 ₫
3.070.779 ₫ total
1 Sept - 2 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 ...
9.4/10 Exceptional! (701 reviews)
"Everything"

Reviewed on 24 Aug 2025

SpringHill Suites by Marriott Winchester
Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

2.5 out of 5
21 Signal Knob Dr, GPS: 35 Brandy court, Strasburg, VA
The price is 1.878.248 ₫ per night from 2 Sept to 3 Sept
1.878.248 ₫
2.090.490 ₫ total
2 Sept - 3 Sept
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! (1,008 reviews)
"The hotel was very clean. The coffee and complimentary breakfast-very disappointing compared to what we get at the Hampton Inn. I tried to check in early (1pm) and was told I would have to pay $20… no other place we stayed has ever required an early check in fee. The place was empty."

Reviewed on 25 Aug 2025

Ramada by Wyndham Strasburg/Shenandoah Valley
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

Default Image

Winchester Historic District

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

Winchester Historic District


Old Town Winchester Travel Guide

Choose two or more items and save on your trip: