Chesapeake Vacation Packages
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Your Chesapeake Vacation
Food, history, entertainment and more … There's so much to discover with a Chesapeake vacation package. And with the ability to customize your city break, it's guaranteed to be one that's tough to forget. Cabin Creek Quilts is one of the famous attractions to put on your to-do list during a trip to Chesapeake. Your ultimate Chesapeake vacation is a couple of clicks away. Browse flights, accommodations and more on Expedia for an adventure that's tailored to suit your travel style.
Top Chesapeake Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Red Roof Inn Charleston - Kanawha City, WV
Kanawha City
Price was CA $886, price is now CA $855 per person
CA $855
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Charleston (CRW)
6.4/10 (1,000 reviews)
Beds were a little hard for my liking but just needed a place to crash after a concert.
Reviewed on Aug. 18, 2025
Holiday Inn Express Charleston-Kanawha City by IHG
Kanawha City
Price was CA $1,020, price is now CA $979 per person
CA $979
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Charleston (CRW)
7.8/10 Good! (596 reviews)
Nice people clean safe
Reviewed on Sep. 7, 2025
Motel 6 Hurricane, WV
Price was CA $909, price is now CA $875 per person
CA $875
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Charleston (CRW)
6/10 (273 reviews)
Advertised it had a pool and it was far from working order. No exterior pictures and we actually thought we were at the wrong place. You have to drive through a parking lot and looks like a slum when you get there. Definitely not a $100+ a night motel.
Reviewed on Jul. 1, 2025
Adventures on the Gorge
Price was CA $1,153, price is now CA $1,113 per person
CA $1,113
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Charleston (CRW)
9.6/10 Exceptional! (27 reviews)
Great for families. Cabin was clean and had everything we needed. Onsite activities were awesome and staff/West Virginia folks were the nicest people. Fayetteville town was great and we enjoyed Cathedral for breakfast and Cantrall’s for chili dogs.
Hotel would be beyond perfect if they added a hot tub and game room for kids! But really it’s perfect!!!
Reviewed on Sep. 1, 2025
Chesapeake Hotel Deals
Embassy Suites Charleston
300 Court St, Charleston, WV
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Sep 14 to Sep 15
CA $165
CA $186 total
Sep 14 - Sep 15
includes taxes & fees
Charleston Marriott Town Center
200 Lee St E, Charleston, WV
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Sep 14 to Sep 15
CA $152
CA $172 total
Sep 14 - Sep 15
includes taxes & fees
Country Inn & Suites By Radisson, Dunbar - Charleston
1007 Dunbar Ave, Building A, Dunbar, WV
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Sep 14 to Sep 15
CA $122
CA $138 total
Sep 14 - Sep 15
includes taxes & fees
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 Chesapeake
Southridge Center
You can do some window-shopping at Southridge Center during your stay in Charleston. Stroll along the riverfront or visit the casinos in this relaxing 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.
