Chesapeake Vacation Packages
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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
Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Newport News (Oyster Point)
Central Newport News
Price was CA $1,517, price is now CA $1,257 per person
CA $1,257
per person
Jul 8 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
8.6/10 Excellent! (609 reviews)
Staff was friendly and the room was clean. Good breakfast offerings. The hallways were rather dingy and need refreshing.
Reviewed on Apr 21, 2026
Comfort Inn & Suites Hampton near Coliseum
Coliseum Central
Price was CA $1,154, price is now CA $998 per person
CA $998
per person
Jul 19 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Norfolk (ORF)
8.8/10 Excellent! (1,225 reviews)
Breakfast was made fresh the lobby area and dining area were both clean, the room was very spacious. Would stay here again
Reviewed on Apr 29, 2026
Comfort Suites Airport
Central Newport News
Price was CA $1,330, price is now CA $1,151 per person
CA $1,151
per person
Jul 8 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
8.8/10 Excellent! (1,014 reviews)
The breakfast in the morning was great and gave you some options to chose from. The hotel has a restaurant listed; however, there is no restaurant onsite. Everything was clean and staff were friendly.
Reviewed on Apr 30, 2026
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.
Chesapeake Hotel Deals
Wingate by Wyndham Chesapeake
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from May 28 to May 29
CA $142
CA $166 total
May 28 - May 29
includes taxes & fees
8/10 Very Good! (1,017 reviews)
Stayed on the fourth floor. Smell of weed hit you as soon as you exited the elevator. Other than that it was a great stay.
Reviewed on Apr 29, 2026
STUDIOS & SUITES 4 LESS CHESAPEAKE
2222 S Military Hwy Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is CA $85 per night from May 18 to May 19
CA $85
CA $101 total
May 18 - May 19
includes taxes & fees
7/10 Good! (790 reviews)
people being loud at night. mentioned issues with the toilet but no one ever came. despite weekly housekeeping that was also hit or miss. high summer pricing in effect but the lack of meaningful amenities and other things don’t justify the weekly rate
Reviewed on May 1, 2026
TRU by Hilton Chesapeake, VA
1570 CROSSWAYS BLVD Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from May 10 to May 11
CA $155
CA $183 total
May 10 - May 11
includes taxes & fees
8.6/10 Excellent! (439 reviews)
No ice bucket and coffee maker in the room. No ice machine on the floor.
Reviewed on May 1, 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
CA $116
per adult
76% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
CA $59
per adult
100% of travellers recommend
City Cruises Norfolk: Signature Brunch Cruise
CA $133
per adult
88% of travellers recommend
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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.
