Chesapeake Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 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
Where to stay in Chesapeake
Find the best Chesapeake areas and neighborhoods for the activities you enjoy most. Learn more about Chesapeake
Greenbrier
4 out of top 10 points of interest in this area
If you're spending some time in Greenbrier, Greenbrier Mall and Chesapeake Arboretum are top sights worth seeing.
Find the Best Chesapeake Vacation Packages
Chesapeake Hotel Deals
Wingate by Wyndham Chesapeake
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is ₩146,018 per night from May 27 to May 28
₩146,018
₩170,864 total
May 27 - May 28
includes taxes & fees
8/10 Very Good! (1,035 reviews)
Everything was good in the hotel other than the tub was clogged when I took a shower.
Reviewed on May 11, 2026
STUDIOS & SUITES 4 LESS CHESAPEAKE
2222 S Military Hwy Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is ₩92,999 per night from May 13 to May 14
₩92,999
₩109,893 total
May 13 - May 14
includes taxes & fees
7/10 Good! (801 reviews)
Good stall
Reviewed on May 10, 2026
YourSpace Hotels Chesapeake
2137 Starmount Parkway Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is ₩159,766 per night from May 27 to May 28
₩159,766
₩186,676 total
May 27 - May 28
includes taxes & fees
9.6/10 Exceptional! (69 reviews)
The property was nice…clean, good fitness center, room was fine. We booked through Expedia for only a 1 night stay and when we arrived to check in, they didn’t have any of the type of room we reserved, so they downgraded. The front desk person basically said our room wasn’t guaranteed because we ...
Reviewed on May 10, 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.
Discover the most popular places to visit in Chesapeake
Lake Drummond
Commune with nature and explore the great outdoors at Lake Drummond during your travels in Chesapeake. Stroll along the beautiful beaches in this romantic area, or check out its top-notch restaurants.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
