Winchester Historic District Vacations from $226
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The Latest Winchester Historic District 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 $399, price is now $226 per person
$226
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (1,294 reviews)
Front desk help was great! Very nice hotel and room.
Reviewed on Oct 28, 2025
Hotel Washington
Downtown Washington D.C.
Save 100% on your flight
Price was $648, price is now $363 per person
$363
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (2,387 reviews)
Perfect hotel to tour DC. Perfect location next to White House and numerous restaurants.
Staff attentive and easy check in and check out
Beautiful lobby area to relax. Delicious hot apple cider offered in lobby was a nice touch but empty within minutes. Staff should check and refill.
Reviewed on Oct 26, 2025
SIXTY DC
Downtown Washington D.C.
Save 100% on your flight
Price was $742, price is now $440 per person
$440
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.6/10 Exceptional! (65 reviews)
Hotel in very nice and super clean, you just can't expect to sleep there. Noisiest hotel on the planet! Wanted to love it , but the clubs and bars in the area attract a drunken crowd of disgusting and inappropriately loud partyiers. It is so loud, the room vibration is in synch with the rooftop club, and the pilice and drunks out front will keep you up past 2am closing. Never, ever, again! 2 stays, both the same!
Reviewed on Oct 27, 2025
Washington Hilton
Northwest
Save 100% on your flight
Price was $634, price is now $376 per person
$376
per person
Jan 3 - Jan 8
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8/10 Very Good! (1,018 reviews)
Staff was nice but the hotel rooms need a serious remodel, also what is up with this destination fee that forces me to spend my money at the hotel restaurant each day.
Reviewed on Oct 30, 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
$127 nightly
The price is $143 total per night from Nov 9 to Nov 10
$143 total
Nov 9 - Nov 10
Total with taxes and fees
9.2/10 Wonderful! (1,005 reviews)
Amazing hotel with lovely rooms, easy parking, near (walking distance ) great restaurants and shops. Highly recommend spa in building.
Reviewed on Oct 23, 2025
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $116 total per night from Dec 2 to Dec 3
$116 total
Dec 2 - Dec 3
Total with taxes and fees
9.2/10 Wonderful! (2,190 reviews)
Amazing
Reviewed on Oct 27, 2025
Red Roof Inn Winchester, VA
991 Millwood Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
$60 nightly
The price is $66 total per night from Dec 1 to Dec 2
$66 total
Dec 1 - Dec 2
Total with taxes and fees
7.4/10 Good! (1,003 reviews)
Good Stay
Good stay for an overnight trip. Kumar treated us like very special people! Clean and very comfortable. Only problem - ADA shower very difficult to use for someone less then 5’4. Reaching the shower head was impossible. Would not recommend this place for special needs.
Reviewed on Oct 22, 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.