Charles Town Vacation Packages
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Your Charles Town Vacation
The adventure-packed city of Charles Town is calling. Discover all its secrets with a Charles Town vacation package that's custom made for you. You'll want to sightsee during your trip to Charles Town. Make time for popular attractions like Hollywood Casino at Charles Town Races, Sleepy Hollow Country Club and Bolivar Heights Scenic Overlook. Whoever you're heading away with and whatever your budget, your ultimate Charles Town vacation is just a few clicks away with Expedia.
Top Charles Town Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Churchill Hotel near Embassy Row
Northwest
Price was CA $936, price is now CA $700 per person
CA $700
per person
Jun 13 - Jun 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
8.8/10 Excellent! (1,004 reviews)
This is a great place if one is not looking for a lot of amenities. Quiet . Bed is good. Great location. Plan to stay there next year for meeting. Staff very friendly and knowledgeable. Menu somewhat limited but tasty.
Reviewed on May 9, 2026
Kimpton Hotel Monaco Washington DC by IHG
Downtown Washington D.C.
Price was CA $1,900, price is now CA $1,359 per person
CA $1,359
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
8.4/10 Very Good! (1,001 reviews)
Great location. Interesting decor.
Reviewed on Apr 15, 2026
Historic Inns of Annapolis
Historic District
Price was CA $1,368, price is now CA $1,023 per person
CA $1,023
per person
Jun 9 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
9/10 Wonderful! (1,845 reviews)
Staff were great! Very friendly. Setting is terrific. We loved our king bed room. Thanks!
Reviewed on May 8, 2026
Salamander Washington DC
Southwest
Price was CA $2,481, price is now CA $1,876 per person
CA $1,876
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
9.4/10 Exceptional! (1,089 reviews)
Rooms over rail tracks would benefit from additional sound-proofing but otherwise fantastic stay
Reviewed on May 7, 2026
Charles Town Hotel Deals
The Inn at Charles Town - Hollywood Casino
100 Hollywood Dr Charles Town WV
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from May 25 to May 26
CA $128
CA $157 total
May 25 - May 26
includes taxes & fees
8.6/10 Excellent! (571 reviews)
Fridge wasnt working
Reviewed on May 8, 2026
Days Inn by Wyndham Charles Town/Harpers Ferry
642 E Washington Street Charles Town WV
Fully refundableReserve now, pay when you stay
The price is CA $101 per night from Jun 1 to Jun 2
CA $101
CA $114 total
Jun 1 - Jun 2
includes taxes & fees
8/10 Very Good! (1,005 reviews)
Definitely stay somewhere else
Reviewed on May 7, 2026
Hampton Inn & Suites Charles Town
157 Pimlico Dr Charles Town WV
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from May 17 to May 18
CA $167
CA $187 total
May 17 - May 18
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
Breakfast was better than decent. Jennifer was the eputomy of customer service, talking with each table about their needs. Front desk were very pleasant in check in and check out. The room was larger than expected with couch and table under TV, microwave, coffee. We thoroughly enjoyed our stay.
Reviewed on Apr 29, 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.
What to do in Charles Town
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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.
