Chesapeake Holidays
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Our guide on where to stay in Chesapeake
Find the best Chesapeake areas and neighborhoods for the activities you enjoy most. Learn more about Chesapeake
Greenbrier East
1 out of top 10 points of interest in this area
If you're spending some time in Greenbrier East, Greenbrier Mall and Jillian's Billiards are top sights worth seeing.
Chesapeake Holiday
Our pick of the best Chesapeake Hotel Deals
Wingate by Wyndham Chesapeake
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is NZ$147 per night from 15 Feb to 16 Feb
NZ$147
15 Feb - 16 Feb
includes taxes & fees
7.8/10 Good! (1,000 reviews)
Great customer service
Reviewed on 2 Feb 2026
Comfort Suites Chesapeake - Norfolk
1550 Crossways Blvd Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is NZ$156 per night from 21 Feb to 22 Feb
NZ$156
21 Feb - 22 Feb
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Clean, comfortable, very nice staff! Bed was extremely comfortable! Nice variety of options for breakfast too. Will continue to use Choice Hotels brand, very happy!
Reviewed on 4 Feb 2026
Fairfield Inn and Suites By Marriott Chesapeake
1560 Crossways Blvd Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is NZ$166 per night from 15 Feb to 16 Feb
NZ$166
15 Feb - 16 Feb
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Tracey at the front desk was a bright light after a very rough LONG day of flights delayed / canceled …. Fast efficient and wonderful! Hotel clean and comfortable! Great breakfast!
Reviewed on 2 Feb 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 family-friendly area or visit its top-notch restaurants.
Chesapeake City Hall
After visiting Chesapeake City Hall, make a plan to see the other sights and activities in Chesapeake. Stroll along the beautiful beaches or attend a sporting event in the area.
What to do in Chesapeake
Ziplining and Climbing at The Adventure Park at Virginia Aquarium
NZ$111
per adult
Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours
NZ$56
per adult
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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.
