Old Town Winchester Vacations from $186
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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.
Glover Park - Georgetown
Northwest
Save 100% on your flight
Price was $484, price is now $290 per person
$290
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
8.8/10 Excellent! (2,562 reviews)
Lovely hotel. Great, spacious room. Excellent, helpful staff.
Reviewed on Sep 5, 2025
Hotel AKA Alexandria
Old Town North
Save 100% on your flight
Price was $716, price is now $454 per person
$454
per person
Nov 10 - Nov 14
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
9.6/10 Exceptional! (542 reviews)
My stay was excellent. Very friendly and accommodating staff. I’ve definitely be back again!! I especially loved the rooftop.
Reviewed on Sep 1, 2025
Hilton Garden Inn Washington DC/U.S. Capitol
Northeast
Save 100% on your flight
Price was $418, price is now $271 per person
$271
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
8/10 Very Good! (1,595 reviews)
Good place to stay. Clean. Good location.
Reviewed on Sep 7, 2025
Arlo Washington DC
Northwest
Save 100% on your flight
Price was $487, price is now $316 per person
$316
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
9.2/10 Wonderful! (883 reviews)
Nice place, very lovely service focused team. The AI front desk function from the room is quick and accurate. The umbrella proactively placed in my room saved me from a very rainy day. Great stay, just farther from the national mall than I would like (20 min walk)
Reviewed on Sep 8, 2025
Old Town Winchester Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St, Winchester, VA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $144 total per night from Sep 21 to Sep 22
$144 total
Sep 21 - Sep 22
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Winchester
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 Sep 11 to Sep 12
$112 total
Sep 11 - Sep 12
Total with taxes and fees
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike, Winchester, VA
Fully refundable
$91 nightly
The price is $99 total per night from Sep 14 to Sep 15
$99 total
Sep 14 - Sep 15
Total with taxes and fees
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.
Discover the most popular places to visit in Old Town Winchester
Handley Regional Library
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
Museum of the Shenandoah Valley
You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
Shenandoah Valley Discovery Museum
You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savor the top-notch restaurants.
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Explore a world of travel with Expedia
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- Car rentals near Nalls Farm Market
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.