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
5 out of top 10 points of interest in this area
While visiting Greenbrier, you might make a stop by sights like Greenbrier Mall and Chesapeake Arboretum.
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
Wingate by Wyndham Chesapeake
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is AU$222 per night from 14 June to 15 June
AU$222
14 June - 15 June
includes taxes & fees
7.8/10 Good! (1,073 reviews)
"There was no phone in the room. I know we have cell phones, but in case of an emergency it would've been nice to have a land line. I didn't gave a remote to the tv. I went to the desk and the girl gave me 3 because she didn't know which one controled the tv in my room! The shampoo and conditioner ..."
Reviewed on 8 June 2026
Comfort Suites Chesapeake - Norfolk
1550 Crossways Blvd Chesapeake VA
The price is AU$212 per night from 14 June to 15 June
AU$212
14 June - 15 June
includes taxes & fees
8.8/10 Excellent! (1,019 reviews)
"Would stay again, definitely."
Reviewed on 8 June 2026
STUDIOS & SUITES 4 LESS CHESAPEAKE
2222 S Military Hwy Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is AU$103 per night from 28 June to 29 June
AU$103
28 June - 29 June
includes taxes & fees
7/10 Good! (829 reviews)
"Nothing"
Reviewed on 5 June 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.
What to do in Chesapeake
City Cruises Norfolk: Signature Dinner Cruise
AU$118
per adult
76% of travellers recommend
City Cruises Norfolk: Signature Brunch Cruise
AU$121
per adult
88% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
AU$59
per adult
100% of travellers recommend
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- 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
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- Visit Portsmouth
- Sandbridge Beach
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- Veterans United Home Loans Amphitheater at Virginia Beach
- Virginia Beach Boardwalk
- Virginia Beach Holidays
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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.
