
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

Sea Ranch Resort
Reviewed on Aug 2, 2026


The Burrus House Inn Waterfront Suites
Reviewed on Jul 30, 2026

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Reviewed on Aug 2, 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

STUDIOS & SUITES 4 LESS CHESAPEAKE
"Great place to stay. Staff was awesome and very clean."
Reviewed on Aug 1, 2026

Hyatt Studios Chesapeake
"Beware you may not get a room! We booked and paid for 2 rooms on Wednesday. When we arrived late Friday we were told they were over booked and there were no rooms available. The staff was zero help, we were on our own. We had to scramble and find other accommodations in the middle of the night. My ..."
Reviewed on Aug 2, 2026

Wyndham Virginia Beach Oceanfront
Stay near popular Chesapeake attractions
What to do in Chesapeake

City Cruises Norfolk: Signature Dinner Cruise

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin



















