Old Town Winchester Vacations from $296
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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.
DoubleTree Hotel Baltimore - BWI Airport
Save 100% on your flight
Price was $436, price is now $296 per person
$296
per person
Apr 11 - Apr 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (1,247 reviews)
Was as expected. And a great last minute room rate.
Reviewed on Mar 2, 2026
The Normandy Hotel
Northwest
Save 100% on your flight
Price was $832, price is now $534 per person
$534
per person
May 21 - May 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.4/10 Very Good! (1,002 reviews)
Great location! Room was small but bed very comfortable. Bathroom was a good size and clean. Would recommend!
Reviewed on Mar 1, 2026
Hyatt Place Arlington/Courthouse Plaza
Court House
Save 100% on your flight
Price was $595, price is now $400 per person
$400
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (1,062 reviews)
Room was clean… location is accessible… breakfast was really room and most of all its the staff !!! They are all fantastic!!!
Superb
Reviewed on Mar 1, 2026
The Melrose Georgetown Hotel
Northwest
Save 100% on your flight
Price was $887, price is now $602 per person
$602
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (2,515 reviews)
I have very comfortable time in Melrose hotel. Everything was excellent. Thank you.
Reviewed on Mar 2, 2026
The Churchill Hotel near Embassy Row
Northwest
Save 100% on your flight
Price was $561, price is now $389 per person
$389
per person
Apr 1 - Apr 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,915 reviews)
Staff was professional, helpful, and friendly!
Reviewed on Feb 16, 2026
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
$122 nightly
The price is $138 total per night from Mar 9 to Mar 10
$138 total
Mar 9 - Mar 10
Total with taxes and fees
9.4/10 Exceptional! (1,006 reviews)
Room was clean but a lil noisy. We didn't have the best room location. Must have been close to a staff area
Reviewed on Mar 2, 2026
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East Winchester VA
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $119 total per night from Mar 5 to Mar 6
$119 total
Mar 5 - Mar 6
Total with taxes and fees
9.2/10 Wonderful! (2,279 reviews)
Clean room. Comfortable bed. Easy in and out. Reasonably close to Old Town Winchester in historic district. Friendly staff.
Reviewed on Mar 1, 2026
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 Mar 8 to Mar 9
$99 total
Mar 8 - Mar 9
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
Great room and service
Reviewed on Mar 2, 2026
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
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.
Jim Barnett Park
4/5(1 review)
Explore the great outdoors at Jim Barnett Park, a lovely green space in 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.