Book Exclusive Chesapeake Vacation Packages

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Chesapeake flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Buckroe Motel

Buckroe Motel

2 out of 5
Price was CA $934, price is now CA $893 per person
CA $893
per person
Dec 17 - Dec 21
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
Stay at this hotel in Hampton. Enjoy free parking, a 24-hour front desk, and housekeeping. Popular attractions Hampton Coliseum and Marketplace at Nickerson are located nearby.
Comfort Suites Airport

Comfort Suites Airport

2.5 out of 5
Central Newport News
Price was CA $1,080, price is now CA $1,020 per person
CA $1,020
per person
Dec 17 - Dec 21
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
Book a stay at this beach hotel in Newport News. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bounce House and Patrick Henry Mall are located nearby.
Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
Coliseum Central
Price was CA $1,029, price is now CA $980 per person
CA $980
per person
Dec 17 - Dec 21
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
Book a stay at this business-friendly hotel in Hampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hampton Coliseum and Peninsula Town Center are located nearby.
Microtel Inn by Wyndham Newport News Airport

Microtel Inn by Wyndham Newport News Airport

2 out of 5
Central Newport News
Price was CA $964, price is now CA $922 per person
CA $922
per person
Dec 17 - Dec 21
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
Book a stay at this business-friendly hotel in Newport News. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Patrick Henry Mall and Hampton Roads Iceplex are located nearby.
James River Inn & Suites

James River Inn & Suites

2.5 out of 5
Briarfield
Price was CA $946, price is now CA $915 per person
CA $915
per person
Dec 17 - Dec 21
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
Stay at this hotel in Newport News. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Hampton Coliseum and Virginia War Museum are located nearby.

Top Chesapeake hotels deals

Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd Chesapeake VA
Free cancellation
The price is CA $117 per night
CA $117
CA $138 total
Dec 14 - Dec 15
includes taxes & fees
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Greenbrier Mall and Waterside District are located nearby.
Pool
Breakfast included
YourSpace Hotels Chesapeake

YourSpace Hotels Chesapeake

3 out of 5
2137 Starmount Parkway Chesapeake VA
Free cancellation
Reserve now, pay when you stay
The price is CA $131 per night
CA $131
CA $153 total
Nov 20 - Nov 21
includes taxes & fees
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Chesapeake Square Mall and Cinemark Chesapeake Square are located nearby.
Pet-friendly
Parking included
SpringHill Suites by Marriott Chesapeake Greenbrier

SpringHill Suites by Marriott Chesapeake Greenbrier

3 out of 5
1446 Crossways Blvd Chesapeake VA
Free cancellation
Reserve now, pay when you stay
The price is CA $177 per night
CA $177
CA $206 total
Nov 15 - Nov 16
includes taxes & fees
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Greenbrier Mall and Waterside District are located nearby.
Pool
Breakfast included
Hyatt Studios Chesapeake

Hyatt Studios Chesapeake

2 out of 5
101 Volvo Parkway Chesapeake VA
Free cancellation
Reserve now, pay when you stay
The price is CA $114 per night
CA $114
CA $134 total
Dec 14 - Dec 15
includes taxes & fees
Stay at this hotel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Greenbrier Mall and Waterside District are located nearby.
Breakfast included
Pet-friendly
Aloft by Marriott Chesapeake

Aloft by Marriott Chesapeake

3 out of 5
1454 Crossways Boulevard Chesapeake VA
Free cancellation
Reserve now, pay when you stay
The price is CA $142 per night
CA $142
CA $166 total
Nov 29 - Nov 30
includes taxes & fees
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Greenbrier Mall and Waterside District are located nearby.
Pool
Pet-friendly
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

3 out of 5
1101 Atlantic Ave Virginia Beach VA
Get rates
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Virginia Beach Boardwalk and First Landing State Park are located nearby.
Pool
Parking included
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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.

Stay near popular Chesapeake attractions

A large building with a prominent arched entrance and a green roof.

Greenbrier Mall

8.4/10 (837 reviews)
You can browse for the perfect souvenirs at Greenbrier Mall during your visit to Chesapeake. Stroll along the beautiful beaches or attend a sporting event in the area.
See properties

Chesapeake Vacations

Whether you're headed off on a few days' break or a long and leisurely vacation, it's a good idea to know some basics about Chesapeake before setting off.

From downtown Norfolk - Virginia Beach, you'll need to head southwest for 8 miles (13 kilometers) to reach this neighborhood.

Places to visit in Chesapeake

Feel like a break in the great outdoors? The countryside at Oak Grove Lake Park is the perfect place to kick a ball around or simply sit back and unwind. And there's more. There's nothing like admiring great art when your mind needs to be nourished. As you marvel at the fabulous pieces at Portlock Galleries at SoNo, try to find a deeper meaning.

Where do you fly into for Chesapeake?

Put your seat in the upright position, fasten your seatbelt and get ready to touch down at Norfolk International Airport (ORF). This is the nearest major terminal and it's approximately 10 miles (16 kilometers) northeast from the middle of Chesapeake. Pick up your bags and start having some fun!

Frequently asked questions

How much are vacation packages to Chesapeake?
Travelocity provides package deals to Chesapeake, including flights and hotels, from an impressive CA $893. With all the extra cash, you could book some cool tours or perhaps even tack on a few extra nights to your getaway.
How long should my Chesapeake vacation be?
There are no strict rules when it comes to how long you should spend in Chesapeake, but most travelers decide to stay around 3 nights. Got some flexibility with your departure date? Consider extending your trip by another night or two. That way, you'll have ample time to check out the area's hidden treasures as well.
Where can I get the best vacation package deals for Chesapeake?
Travelocity is here to help you find an awesome Chesapeake package deal. With no less than 400 partner airlines and 1,000,000 properties worldwide, you're bound to find the perfect mix.
Why should I purchase my Chesapeake vacation bundle with Travelocity?
Nothing beats the feeling of knowing you've bagged the best price in town — that's our Price Match Guarantee. Add to that our impressively broad range of destinations and 24/7 team of customer service professionals and you've got the blueprint for a hassle-free vacation.
Can I save on my Chesapeake car rental if I book it with my hotel or flight?
With a Chesapeake vacation package, you can combine your hotel, flight and car bookings and save a nice amount. If you're eager to see the best of this fabulous city, why not check out Busch Gardens Williamsburg? This well-known sight is 64 kilometers from Chesapeake. With a rental car, you'll be there in no time.
Which airport is best for Chesapeake?
Many tourists arrive at Norfolk Intl. Airport (ORF). After you've stepped off the plane and grabbed your bags, you'll need to head 16 kilometers southwest to reach central Chesapeake. Newport News - Williamsburg Intl. Airport (PHF) is another option, 48 kilometers from the heart of the city.
What is there to do in Chesapeake?
Chesapeake is full of places to discover, such as Chesapeake City Park and Chesapeake City Hall. These well-known attractions are at the top of most people's must-see lists.
Where should I stay when visiting Chesapeake?
Many visitors opt to check in to the Hyatt Place Chesapeake. It's an excellent base for your Chesapeake vacation.

Photos of local treasures

Browse Chesapeake vacation photos for more inspiration

A beach at sunset with a pier extending into the water.
A calm lake at sunset with a rocky shoreline and tall grasses reflecting the sky.
A beach with a clear sky, calm sea, and a distant shoreline.
A solitary tree silhouetted against a sunset sky, reflected in calm water.
A sunset over a calm sea with wooden posts in the foreground.