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

Eurostars Saint Gregory Dupont Circle Georgetown
Downtown Washington D.C.
Price was CA $1,021, price is now CA $809 per person
CA $809
per person
Jul 24 - Jul 28
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.8/10 Excellent! (1,004 reviews)
Property is clean but well overdue for updates. The room was old and dated. It had a broken bathroom vanity and our AC was barely working. AC required multiple resets to get it to blow cold air, it was extremely loud when it turned on, and required to be reset multiple times throughout our 3 nights there. When informed of the poorly working AC, staff offered very minimal solutions. No on was on site to fix the issue, no room change offered and no compensation offered. No follow up was done with us to ensure that the issue had been fixed after we informed them we were able to reset our AC ourselves. Would definitely not stay again.
Reviewed on Jun 18, 2026

Swanendele Inn at St. Mary's Maryland
Price was CA $3,913, price is now CA $2,887 per person
CA $2,887
per person
Aug 22 - Aug 29
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Baltimore (BWI)
9.8/10 Exceptional! (33 reviews)
Everything about the Swanendele Inn was exceptional: the location, the accommodations, the facilities, the decor, the hosts, and, not least, the breakfast. In fact, you could spend several days just exploring the remarkable antiques and artifacts around the place. However, what made the strongest impression was the fiery glow of dawn though the pine trees outside our balcony every morning in the Margeret Brent suite. Rhododaktylos, "The rosy-fingered dawn": I never understood the true meaning of that phrase until I saw that.
Reviewed on Aug 4, 2025

Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
Price was CA $1,210, price is now CA $897 per person
CA $897
per person
Jul 24 - Jul 28
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (1,194 reviews)
Excellent location and a few blocks walking distance to the White House. We were tired and hungry upon check-in and didn't want to leave the premise to look for a place to eat. We were both pleasantly surprised to discover the on-site restaurant at the front entrance. We checked in on a weekday and were able to get a table without a reservation. The restaurant had a French style bistro ambiance and the food and cocktails were delicious. Our reservation included a bottle of wine, which we didn't get initially and had to call in as a reminder. Right away staff apologized and sent up our bottle of wine. Overall, a pleasant experience and five stars for location.
Reviewed on Jun 21, 2026

Comfort Inn & Suites Lexington Park near Pax River
Price was CA $1,304, price is now CA $982 per person
CA $982
per person
Aug 22 - Aug 29
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Baltimore (BWI)
8.6/10 Excellent! (706 reviews)
Clean and quiet and friendly staff! Breakfast options are limited and could use an expansion. Otherwise, my stay was exceptional and would come back again!
Reviewed on Jun 7, 2026

Kellogg Conference Hotel at Gallaudet University
Northeast
Price was CA $1,103, price is now CA $839 per person
CA $839
per person
Jul 27 - Jul 31
just found
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.2/10 Very Good! (1,022 reviews)
This is a safe, nice hotel on a college campus in a great location of DC. The staff was friendly and professional. The only thing we had an issue is with allergies. Seemed like a dust issue as the rooms all have the air conditioning with recycled air. Overall great property.
Reviewed on Jun 15, 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
The price is CA $185 per night from Jul 5 to Jul 6
CA $185
CA $209 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (1,006 reviews)
"Historic hotel in a convenient area."
Reviewed on Jun 21, 2026

Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Jul 5 to Jul 6
CA $137
CA $156 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"Staff was friendly and responsive. Room was clean. We did not use amenities, but they seemed nice enough"
Reviewed on Jun 21, 2026

TRU By Hilton Winchester
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from Jul 5 to Jul 6
CA $98
CA $108 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (975 reviews)
"An “Excellent” rating is True for “TRU”. Plenty of parking space, lively staff, vibrant interiors and decor, work space and game options, adequate luggage karts, clean rooms, and hot breakfast. Everything that needs to be in place was in place for a comfortable and peaceful stay."
Reviewed on Jun 21, 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.
Frequently asked questions
Discover the most popular places to visit in Old Town Winchester

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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.






