Chesapeake Holidays
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Your Chesapeake Holiday
Pick a Chesapeake holiday package and you can prioritize what matters — enjoying yourself. No more planning hassles, just more free time to immerse yourself in the delights of this fascinating city, such as its rich history and family-friendly attractions. Eager to get out and explore? Greenbrier Mall, Chesapeake City Park and Chesapeake City Hall are just three of the most popular places to visit during a trip to Chesapeake. No matter your travel plans or the size of your budget, organising your ultimate tailored Chesapeake holiday is simple with Expedia.
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
Chesapeake Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Norfolk Intl. Airport (ORF) |
Population | 235,400 |
Max Temp Winter | 10ºC |
Max Temp Summer | 29ºC |
Top Sights | Jillians Billiards, Portlock Galleries at SoNo and Chesapeake City Park |
Our pick of the best Chesapeake Hotel Deals
Comfort Suites Chesapeake - Norfolk
1550 Crossways Blvd Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is AU$138 per night from 15 Dec to 16 Dec
AU$138
15 Dec - 16 Dec
includes taxes & fees
8.4/10 Very Good! (1,008 reviews)
Staff was extremely courteous.
Reviewed on 18 Nov 2025
STUDIOS & SUITES 4 LESS CHESAPEAKE
2222 S Military Hwy Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is AU$93 per night from 28 Dec to 29 Dec
AU$93
28 Dec - 29 Dec
includes taxes & fees
6.6/10 (651 reviews)
Staff is very friendly. The keep the property and room very clean . Loved the updated deluxe room
Reviewed on 23 Nov 2025
Wingate by Wyndham Chesapeake
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is AU$143 per night from 8 Dec to 9 Dec
AU$143
8 Dec - 9 Dec
includes taxes & fees
8/10 Very Good! (1,003 reviews)
Good location, clean, friendly staff
Reviewed on 21 Nov 2025
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.
What to do in Chesapeake
Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours
AU$49
per adult
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Lodging
- Hotels near Douglas MacArthur Memorial
- Greenbrier East Hotels
- Hotels near Greenbrier Mall
- Luxury Hotels in Greenbrier West
- Motels in MacArthur Square Station
- Apartments in Norfolk
- B&B in Norfolk
- Cabin Rentals in Norfolk
- Condominium Resort in Norfolk
- Condo Rentals in Norfolk
- Cottages in Norfolk
- Holiday Homes in Norfolk
- All Inclusive Hotels in Norfolk
- Cheap Hotels in Norfolk
- Hilton Hotels in Norfolk
- Langham Hotels in Norfolk
- Luxury Hotels in Norfolk
- Motel 6 Hotels in Norfolk
- Romantic Hotels in Norfolk
- Spa Hotels in Norfolk
- Norfolk Hotels
- Caravan Parks in Norfolk Station
- Beach Hotels in Portsmouth
- Business Hotels in Portsmouth
- Hotels with Parking in Portsmouth
- Pet Friendly Hotels in Portsmouth
- Portsmouth Hotels
- Hotels near Portsmouth Naval Shipyard Museum
- Hotels near Town Point Park
Flights
- Flights to Portsmouth City County
- Flights to Norfolk
- Flights to Portsmouth
- Flights from Matthew Town to Norfolk
- Flights from Kinshasa to Norfolk
- Flights from Freedom to Norfolk
- Flights from New York to Norfolk
- Flights from Perth to Norfolk
- Flights from West Lebanon to Norfolk
- Flights from Margate to Norfolk
- Flights from Mauke to Norfolk
- Flights from Nondalton to Norfolk
- Flights from Norfolk
- Flights from Bissau to Norfolk
- Flights from Dawson City to Norfolk
- Flights from York Landing to Norfolk
- Flights from Bedford to Norfolk
- Flights from Paisley to Norfolk
- Flights from Taos to Norfolk
- Flights from Cheyenne to Norfolk
- Flights from Harrisonburg to Norfolk
- Flights from Oxford to Norfolk
- Flights from Cartersville to Norfolk
- Flights from Corbin to Norfolk
- Flights from Artesia to Norfolk
- Flights from Gwaunaru'u to Norfolk
- Flights from Bishop to Norfolk
- Flights from Derby to Norfolk
- Flights from Ipswich to Norfolk
- Flights from Chatham Island to Norfolk
- Flights from Oxford to Norfolk
Packages
- Busch Gardens Williamsburg
- Carrollton Nike Park
- Chesapeake Bay Bridge-Tunnel
- Colonial National Historical Park
- Edgar Cayce's Association for Research and Enlightenment
- False Cape State Park
- First Landing State Park
- Hampton Holidays
- Hermitage Museum and Gardens
- Hilltop Shopping Center
- Historic Jamestowne
- Huntington Park
- Ivor Holidays
- Military Aviation Museum
- Mount Trashmore Park
- Nauticus National Maritime Center
- Naval Station Norfolk
- Neptune Statue
- Neptune's Park
- Norfolk - Virginia Beach Holidays
- Norfolk Holidays
- Visit Norfolk
- Ocean View Holidays
- Ordinary Holidays
- Portsmouth Holidays
- Visit Portsmouth
- Sandbridge Beach
- Suffolk Holidays
- Veterans United Home Loans Amphitheater at Virginia Beach
- Virginia Beach Boardwalk
- Virginia Beach Holidays
- Williamsburg Holidays
Holiday Rentals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
