Winchester Historic District Vacations from $156
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The Latest Winchester Historic District Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Arboretum
Northeast
Price was $326, price is now $156 per person
$156
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
8/10 Very Good! (1,007 reviews)
You have to pay for the parking even though the parking lot empty and there are not many cars
Reviewed on Aug 26, 2025
DoubleTree by Hilton Hotel Laurel
West Laurel
Save 100% on your flight
Price was $512, price is now $276 per person
$276
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,006 reviews)
Convenient external room door made it easy walking my dog. Did not have to walk thru.obby.
Reviewed on Aug 24, 2025
InterContinental Washington D.C. - The Wharf by IHG
The Wharf
Save 100% on your flight
Price was $1,190, price is now $708 per person
$708
per person
Oct 2 - Oct 7
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
9.4/10 Exceptional! (1,000 reviews)
Amazing view! Rooftop pool was great and the dinner options were excellent.
Reviewed on Aug 27, 2025
Club Quarters Hotel in Washington DC
Downtown Washington D.C.
Save 100% on your flight
Price was $366, price is now $217 per person
$217
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
8.8/10 Excellent! (1,643 reviews)
Convenient to White House and Philippine Embassy
Reviewed on Aug 26, 2025
The St. Gregory Hotel
Downtown Washington D.C.
Save 100% on your flight
Price was $538, price is now $325 per person
$325
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
8.6/10 Excellent! (1,006 reviews)
Good location, friendly staff, great breakfast, clean and quiet rooms, best sleep in a week
Reviewed on Aug 12, 2025
Winchester Historic District Hotel Deals
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St, Winchester, VA
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $142 total per night from Aug 31 to Sep 1
$142 total
Aug 31 - Sep 1
Total with taxes and fees
9.2/10 Wonderful! (1,009 reviews)
"Great time relaxing in old town Winchester"
Reviewed on Aug 24, 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 Sep 1 to Sep 2
$112 total
Sep 1 - Sep 2
Total with taxes and fees
9.2/10 Wonderful! (2,136 reviews)
"The bedroom was clean. Some area a bit older looking but good. Hall ways a little smelly like needs carpets refreshed. But not all that bad.."
Reviewed on Aug 25, 2025
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike, Winchester, VA
Fully refundable
$85 nightly
The price is $92 total per night from Sep 7 to Sep 8
$92 total
Sep 7 - Sep 8
Total with taxes and fees
9/10 Wonderful! (1,007 reviews)
"Clean and staff was great."
Reviewed on Aug 23, 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 Winchester Historic District
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 top-notch restaurants or charming coffeehouses 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.