
Chesapeake Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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



Magnuson Hotel Virginia Beach
Reviewed on Apr 29, 2026


Hampton Inn & Suites Newport News (Oyster Point)
Reviewed on May 3, 2026
Where to stay in Chesapeake

Greenbrier
If you're spending some time in Greenbrier, Greenbrier Mall and Chesapeake Arboretum are top sights worth seeing.
Chesapeake Hotel Deals

Wingate by Wyndham Chesapeake
Breakfast should be at least until 11. In the bathtub, there should be a mat or bathmats inside the bathtub, as the bathtub was extremely slippery.
Reviewed on May 10, 2026

STUDIOS & SUITES 4 LESS CHESAPEAKE
very clean and friendly employee
Reviewed on May 9, 2026

TRU by Hilton Chesapeake, VA
Everything was great I love the pancake maker
Reviewed on May 9, 2026
What to do in Chesapeake

City Cruises Norfolk: Signature Dinner Cruise

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin












