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 ₹11,160 per night from 21 Sept to 22 Sept
₹11,160
₹12,644 total
21 Sept - 22 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! (1,000 reviews)
"Perfect location to visit for business or pleasure!"

Reviewed on 7 Sep 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
Fully refundableReserve now, pay when you stay
The price is ₹9,544 per night from 14 Sept to 15 Sept
₹9,544
₹10,384 total
14 Sept - 15 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! (2,138 reviews)
"We mistakenly left a watch in the room after we checked out, and the front-desk person let us go back to check the room about an hour later. Fortunately, the watch was found!"

Reviewed on 9 Sep 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
Fully refundableReserve now, pay when you stay
The price is ₹7,754 per night from 14 Sept to 15 Sept
₹7,754
₹8,701 total
14 Sept - 15 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! (1,000 reviews)
"Very clean & comfortable. Staff was very helpful & pleasant."

Reviewed on 8 Sep 2025

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

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike, Winchester, VA
The price is ₹6,080 per night from 11 Sept to 12 Sept
₹6,080
₹6,616 total
11 Sept - 12 Sept
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 breakfast and the helpful staff in their reviews. ...
8.4/10 Very Good! (1,090 reviews)
"Staff is very accommodating and efficient. Room was clean, bed very comfortable. Housekeeper does a fantastic job. Breakfast is very good. Hotel is pet friendly which we appreciate."

Reviewed on 7 Sep 2025

Travelodge by Wyndham Winchester
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 ₹7,402 per night from 21 Sept to 22 Sept
₹7,402
₹8,053 total
21 Sept - 22 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! (1,331 reviews)
"Staff was especially friendly & welcoming, and I appreciated the small $25 pet fee!"

Reviewed on 10 Sep 2025

Microtel Inn & Suites by Wyndham 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 ₹6,291 per night from 16 Sept to 17 Sept
₹6,291
₹7,002 total
16 Sept - 17 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! (1,002 reviews)
"Spacious clean room. Excellent breakfast especially the pancake machine."

Reviewed on 5 Sep 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

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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