Old Town Winchester Vacations from $341

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Your Old Town Winchester Vacation

Book a customized vacation package to Old Town Winchester and experience the wonders of this neighborhood from sunup to sundown. From its cafes and history to its distinct personality and vibe, there are loads of good reasons to visit Old Town Winchester. Hoping to sightsee during your trip to Old Town Winchester? Don't miss nearby attractions like Shenandoah University, Museum of the Shenandoah Valley and Apple Blossom Mall. Stop daydreaming and start doing. When it's time to book your ideal vacation to Old Town Winchester, Expedia will help get you there.

The Latest Old Town Winchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Kellogg Conference Hotel at Gallaudet University
InterContinental Washington D.C. - The Wharf by IHG
The Bethesdan Hotel, Tapestry Collection by Hilton
The LINE Hotel DC
citizenM Washington DC Capitol

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
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $136 total per night from Aug 2 to Aug 3
$136 total
Aug 2 - Aug 3
Total with taxes and fees
9.4/10 Exceptional! (1,016 reviews)
"Very good restaurant and staff. Highly recommend This hotel it's very old but up to date,large well furnished rooms and great bed."

Reviewed on Jul 8, 2026

The George Washington Hotel, A Wyndham Grand Hotel
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Jul 26 to Jul 27
$90 total
Jul 26 - Jul 27
Total with taxes and fees
9.2/10 Wonderful! (1,032 reviews)
"The room was very narrow. Only one person could pass tge bed at a time. There was no dressers to out clothes in. They only had hooks that you could hang up clothes. There was no closet in the room and no microwave. The only garbage pail was a small pail that was divided in half without a bag which ..."

Reviewed on Jul 13, 2026

TRU By Hilton 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 refundable
$86 nightly
The price is $95 total per night from Aug 2 to Aug 3
$95 total
Aug 2 - Aug 3
Total with taxes and fees
9.2/10 Wonderful! (1,017 reviews)
"Highly recommend. Good location and great amenities. Very clean."

Reviewed on Jul 12, 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.