Old Town Winchester Vacations from $332
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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.
Lyle Washington D.C.
Northwest
Save 100% on your flight
Price was $850, price is now $474 per person
$474
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,603 reviews)
The room was well-appointed with some thoughtful touches that made a longer stay more comfortable. The gym was better than an average hotel gym. The location is convenient to Dupont Circle, and I'd definitely stay again.
Reviewed on Dec 10, 2025
Eurostars Saint Gregory Dupont Circle Georgetown
Downtown Washington D.C.
Save 100% on your flight
Price was $637, price is now $365 per person
$365
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (1,008 reviews)
Exceptionally friendly and accommodating staff.
Reviewed on Dec 10, 2025
The Watergate Hotel
Northwest
Save 100% on your flight
Price was $895, price is now $522 per person
$522
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,059 reviews)
As always, the staff at the Watergate is warm and welcoming. The rooms are immaculate and the food is amazing.
Reviewed on Dec 2, 2025
Embassy Suites by Hilton Washington D.C. – Convention Center
Downtown Washington D.C.
Save 100% on your flight
Price was $908, price is now $531 per person
$531
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (2,031 reviews)
Staff was kind, rooms were clean, breakfast was decent. My only 2 complaints, which are not biggies, are that the beds are not comfortable and that i didnt like being harrassed daily to buy a vacation package for hilton. I would however stay here again.
Reviewed on Dec 1, 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 $143 total per night from Dec 21 to Dec 22
$143 total
Dec 21 - Dec 22
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
Old building has character.
Reviewed on Dec 7, 2025
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 Jan 11 to Jan 12
$112 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
9.2/10 Wonderful! (2,221 reviews)
Comfortable and clean room.
Reviewed on Dec 9, 2025
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $79 total per night from Jan 7 to Jan 8
$79 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
9/10 Wonderful! (1,375 reviews)
Everything was great. Had to leave early in the morning because of a snowy weather forecast- missed breakfast.
Reviewed on Dec 7, 2025
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
5/5(2 reviews)
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
5/5(19 reviews)
You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.
Shenandoah Valley Discovery Museum
4.5/5(11 reviews)
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.