Old Town Winchester, VA

Winchester

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

Popular places to visit


Old Town Winchester Hotel Deals

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 R$ 647 per night from Aug 31 to Sep 1
R$ 647
R$ 733 total
31 Aug - 1 Sep
includes taxes & fees
Stay at this 3.5-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our ...
9.2/10 Wonderful! (1,001 reviews)
"Hotel has a walking mall right around the corner. Beds and pillows are always comfortable. Has nightly entertainment on weekends onsite at the Bar/Restaurant."

Reviewed on 19 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 R$ 562 per night from Sep 1 to Sep 2
R$ 562
R$ 611 total
1 Sep - 2 Sep
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (2,129 reviews)
"Just a suggestion. I am disabled and was placed in a lovely room on the 6th floor. The fire alarm went off and my concern is how is someone in a wheelchair going to evacuate without the elevator. Maybe all ada rooms shou"

Reviewed on 19 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 R$ 449 per night from Aug 31 to Sep 1
R$ 449
R$ 505 total
31 Aug - 1 Sep
includes taxes & fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,003 reviews)
"It was a great stay for what we needed! A comfortable place to stay while exploring Winchester each day. Pool was a great touch and the front desk lady was helpful and nice! Will be back again!"

Reviewed on 21 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 R$ 434 per night from Sep 15 to Sep 16
R$ 434
R$ 472 total
15 Sep - 16 Sep
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,324 reviews)
"easy to get to, close to where I needed to be."

Reviewed on 19 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 R$ 636 per night from Aug 24 to Aug 25
R$ 636
R$ 692 total
24 Aug - 25 Aug
includes taxes & fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (694 reviews)
"Fabulous all around. Comfortable beds, great breakfast, super clean and great staff. Great stay!"

Reviewed on 20 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 R$ 391 per night from Sep 1 to Sep 2
R$ 391
R$ 435 total
1 Sep - 2 Sep
includes taxes & fees
Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,000 reviews)
A night in Virginia
"Room was comfortable. The breakfast was decent. The Mexican restaurant attached is AMAZING. No conditioner and body wash was super low. I’m sure I could have gotten more if I asked but it was not a big deal. I did ask for more towels and they were quickly accommodating."

Reviewed on 19 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 neighborhoods 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, VA

Choose two or more items and save on your trip: