
Winchester Historic District Vacation Packages
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Top Holiday Package Deals in Winchester Historic District
Price found within the past 48 hours. Click for updated prices.

The Churchill Hotel near Embassy Row
Northwest
Price was CA $1,330, price is now CA $833 per person
CA $833
per person
Oct 13 - Oct 16
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (WAS)
8.8/10 Excellent! (1,830 reviews)
Be aware that random amounts will be taken from your account that the card you use for incidentals is associated with. I was not informed at any time that this would occur and the amounts taken out, three times, had a major impact on my trip as I had budgeted and did not anticipate I would have all these debits that would mean I could not afford to eat and had to skip a planned excursion. I was told the amounts were usually small but again was NEVER told the debits would occur. I have been trying to resolve this for close to a week now with an email having been sent, two voicemail being left but no one has responded to let me know how this would be resolved. The hotel is in a nice part of town, a quick drive to most “tourist” locations, the room was very nice and spacious, the on site restaurant was nice as well but having money taken from your account that has a significant impact on your trip, that you were not told would occur would be the biggest drawback for this hotel along with being informed as to when you’d have the funds returned which hasn’t occurred as of this writing.
Reviewed on Aug. 22, 2025

The St. Gregory Hotel
Downtown Washington D.C.
Price was CA $2,041, price is now CA $1,137 per person
CA $1,137
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) 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

SIXTY DC
Downtown Washington D.C.
Price was CA $1,623, price is now CA $987 per person
CA $987
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Washington (WAS)
9.8/10 Exceptional! (39 reviews)
The staff were outstanding and made for a great experience and the room was fabulous! The rooftop bar is beautiful and we had a great time!
Reviewed on Aug. 22, 2025

Rosewood Washington, D.C.
Northwest
Price was CA $5,799, price is now CA $3,621 per person
CA $3,621
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Washington (WAS)
9.2/10 Wonderful! (187 reviews)
Enjoyed my stay here. Our room was spacious. The staff were friendly. A lovely staff member named Abrehet was most especially helpful, and accommodating! Will be back.
Reviewed on Jul. 8, 2025

Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
Price was CA $1,951, price is now CA $1,226 per person
CA $1,226
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Washington (WAS)
9/10 Wonderful! (1,009 reviews)
Love the stay at the hotel. The breakfast experience could have been better but the food was great. The shower head at the bath tub could improve water pressure. Overall great experience.
Reviewed on Aug. 25, 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
The price is CA $163 per night from Sep 1 to Sep 2
CA $163
CA $185 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
Super Getaway
"Great old hotel. Quiet, comfortable, beautiful. Staff were wonderful. Perfect location for walking around the downtown mall."
Reviewed on Aug. 23, 2025

La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Sep 1 to Sep 2
CA $142
CA $154 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (2,130 reviews)
"A"
Reviewed on Aug. 22, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is CA $113 per night from Sep 7 to Sep 8
CA $113
CA $128 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"It was a great stay for what we needed! A comfortable place to stay while exploring Winchester each day. Pool was a great touch and the front desk lady was helpful and nice! Will be back again!"
Reviewed on Aug. 21, 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
Jim Barnett Park
Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
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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.