
Chesapeake Vacation Packages
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Your Chesapeake Vacation
Lock in a Chesapeake vacation package and concentrate on what matters — enjoying yourself. No more planning headaches, just a lot more free time to uncover what's special about this lively city, such as its rich history and family-friendly attractions. Make your trip to Chesapeake even more fun by including some sightseeing. Greenbrier Mall, Oak Grove Lake Park and Chesapeake City Park are among the popular attractions you'll want to explore. Your perfect Chesapeake vacation is just clicks away. Search flights, hotels and more on Expedia for a trip that's tailored just for you.
Top Chesapeake Vacation Deals

The Ocean Key Virginia Beach Resort
Reviewed on Aug. 16, 2025

The Capes Hotel
Reviewed on Jul. 22, 2025

Coastal Hotel and Suites Virginia Beach Oceanfront
Reviewed on Aug. 17, 2025

Holiday Inn & Suites Virginia Beach North Beach by IHG
Reviewed on Aug. 18, 2025

Hampton Inn & Suites Newport News (Oyster Point)
Reviewed on Aug. 17, 2025
Where to stay in Chesapeake

Greenbrier East
While visiting Greenbrier East, you might make a stop by sights like Greenbrier Mall and Jillian's Billiards.
Chesapeake Hotel Deals

STUDIOS & SUITES 4 LESS CHESAPEAKE
Reviewed on Aug. 14, 2025

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
Reviewed on Aug. 17, 2025

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection
Reviewed on Aug. 17, 2025
What to do in Chesapeake

Spirit of Norfolk Signature Dinner Cruise

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours
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