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.
Comfort Suites Airport
Central Newport News
Price was CA $1,345, price is now CA $1,144 per person
CA $1,144
per person
Aug 14 - Aug 21
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Norfolk (ORF)
8.8/10 Excellent! (1,000 reviews)
Room was great and very well priced. Staff was friendly. Breakfast was phenomenal
Reviewed on Jun 23, 2026
Sea Ranch Resort
Price was CA $1,762, price is now CA $1,386 per person
CA $1,386
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
8.6/10 Excellent! (1,006 reviews)
Enjoyed the friendly and helpful staff. Breakfast at the restaurant was delicious.
Reviewed on Jun 22, 2026
Hampton Inn & Suites Newport News (Oyster Point)
Central Newport News
Price was CA $1,515, price is now CA $1,266 per person
CA $1,266
per person
Aug 14 - Aug 21
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Norfolk (ORF)
8.8/10 Excellent! (624 reviews)
Everything is good 👍
Reviewed on Jun 14, 2026
The Ocean Key Virginia Beach Resort
Northeast Virginia Beach
Price was CA $1,800, price is now CA $1,506 per person
CA $1,506
per person
Aug 12 - Aug 16
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
7.6/10 Good! (1,535 reviews)
We loved the location and the price for a 2bd/2ba was great!
We loved having the pool but wished it was a bit bigger as we were not the only ones that loved it.
Reviewed on Jun 23, 2026
The Lodge at Kiln Creek Resort
Central Newport News
Price was CA $1,861, price is now CA $1,581 per person
CA $1,581
per person
Aug 14 - Aug 21
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Norfolk (ORF)
9/10 Wonderful! (221 reviews)
We were very impressed by this property. Staff was very helpful, rooms clean and well maintained. On site restaurant very convenient. Location central to greater Newport News area. Would definitely stay again.
Reviewed on May 17, 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
STUDIOS & SUITES 4 LESS CHESAPEAKE
2222 S Military Hwy Chesapeake VA
The price is CA $85 per night from Jun 30 to Jul 1
CA $85
CA $101 total
Jun 30 - Jul 1
includes taxes & fees
7.2/10 Good! (848 reviews)
"Location was great. Floor was dirty."
Reviewed on Jun 23, 2026
Wingate by Wyndham Chesapeake
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Jul 5 to Jul 6
CA $169
CA $197 total
Jul 5 - Jul 6
includes taxes & fees
7.8/10 Good! (1,090 reviews)
"The Friendly staff was the best part of my stay here!"
Reviewed on Jun 20, 2026
YourSpace Hotels Chesapeake
2137 Starmount Parkway Chesapeake VA
The price is CA $168 per night from Jun 30 to Jul 1
CA $168
CA $197 total
Jun 30 - Jul 1
includes taxes & fees
9.6/10 Exceptional! (109 reviews)
"Awesome place to stay! Shocked that our rooms had full size refrigerators, a washer and dryer and dishwasher and a small cooktop as well as microwave. Room was very nice and clean and the staff could not have been more accommodating. The two little goats wandering in the parking lot the morning of ..."
Reviewed on Jun 22, 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 $117
per adult
76% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
CA $59
per adult
100% of travellers recommend
Ziplining and Climbing at The Adventure Park at Virginia Aquarium
CA $89
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.
