Old Town Winchester Vacations from $203

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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.
InterContinental Washington D.C. - The Wharf by IHG
Park Hyatt Washington
SIXTY DC
Sofitel Washington DC Lafayette Square
Kellogg Conference Hotel at Gallaudet University

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
$127 nightly
The price is $144 total per night from Oct 26 to Oct 27
$144 total
Oct 26 - Oct 27
Total with taxes and fees
9.2/10 Wonderful! (1,010 reviews)
"I’d return for sure. Our room was wonderful."

Reviewed on Oct 10, 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
$103 nightly
The price is $112 total per night from Nov 2 to Nov 3
$112 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (2,184 reviews)
"Was just one night with group of friends. Location was great, easy check in and out, good breakfast and comfy beds. Would highly recommend."

Reviewed on Oct 12, 2025

La Quinta Inn & Suites by Wyndham Winchester
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 out of 5
640 East Jubal Early Drive, Winchester, VA
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $129 total per night from Nov 2 to Nov 3
$129 total
Nov 2 - Nov 3
Total with taxes and fees
9/10 Wonderful! (1,019 reviews)
"Great stay! Would definitely would stay again!"

Reviewed on Oct 10, 2025

Hampton Inn Winchester-University/Mall Area
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.