Book Exclusive Chesapeake Vacation Packages

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Chesapeake flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Mulberry Inn

Mulberry Inn

2.5 out of 5
North Newport News
Price was CA $1,077, price is now CA $910 per person
CA $910
per person
Feb 28 - Mar 7
found 1 day 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 Busch Gardens Williamsburg and Lee Hall Mansion are located nearby.
Spacious 4BR Home w/ Pool Family Friendly

Spacious 4BR Home w/ Pool Family Friendly

3 out of 5
Central Newport News
Price was CA $3,293, price is now CA $2,648 per person
CA $2,648
per person
Feb 28 - Mar 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
Stay at this 3-star cottage in Newport News. Enjoy free parking, a garden, and patios. Popular attractions Lee Hall Mansion and Patrick Henry Mall are located nearby.
Comfort Suites Airport

Comfort Suites Airport

2.5 out of 5
Central Newport News
Price was CA $1,271, price is now CA $1,057 per person
CA $1,057
per person
Feb 28 - Mar 7
found 1 day 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 Patrick Henry Mall and Newport News Park are located nearby.
Hampton Inn & Suites Newport News (Oyster Point)

Hampton Inn & Suites Newport News (Oyster Point)

2.5 out of 5
Central Newport News
Price was CA $1,379, price is now CA $1,151 per person
CA $1,151
per person
Feb 28 - Mar 7
found 1 day 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.
Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
Coliseum Central
Price was CA $1,313, price is now CA $1,114 per person
CA $1,114
per person
Feb 28 - Mar 7
found 1 day 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.

Top Chesapeake hotels deals

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

2.5 out of 5
817 Greenbrier Circle Chesapeake VA
Free cancellation
Reserve now, pay when you stay
The price is CA $109 per night
CA $109
CA $128 total
Jan 15 - Jan 16, 2026
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 breakfast and the helpful staff in our reviews. Popular attractions Greenbrier Mall and AMF Indian River Lanes are located nearby.
Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd Chesapeake VA
Free cancellation
Reserve now, pay when you stay
The price is CA $92 per night
CA $92
CA $109 total
Dec 21 - Dec 22
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 Chesapeake City Park are located nearby.
Aloft Chesapeake

Aloft Chesapeake

3 out of 5
1454 Crossways Boulevard Chesapeake VA
Free cancellation
Reserve now, pay when you stay
The price is CA $114 per night
CA $114
CA $134 total
Jan 4 - Jan 5, 2026
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 Oak Grove Lake Park are located nearby.
Holiday Inn Express Chesapeake - Norfolk by IHG

Holiday Inn Express Chesapeake - Norfolk by IHG

2.5 out of 5
721 Conference Center Drive Chesapeake VA
Free cancellation
The price is CA $109 per night
CA $109
CA $128 total
Dec 21 - Dec 22
includes taxes & fees
Stay at this 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 AMF Indian River Lanes are located nearby.
Days Inn by Wyndham Chesapeake

Days Inn by Wyndham Chesapeake

2 out of 5
1439 Geo. Washington Hwy Chesapeake VA
Free cancellation
Reserve now, pay when you stay
The price is CA $72 per night
CA $72
CA $86 total
Dec 21 - Dec 22
includes taxes & fees
Book a stay at this business-friendly motel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the property condition in our reviews. Popular attractions Brentwood Play Area and Rivers Casino Portsmouth are located nearby.
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

3 out of 5
1801 Atlantic Ave Virginia Beach VA
Free cancellation
The price is CA $130 per night
CA $130
CA $152 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Book a stay at this beach hotel in Virginia Beach. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Virginia Beach Boardwalk and John Wareing Monument are located nearby.
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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.

Popular places to visit

Greenbrier Mall

Greenbrier Mall

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.

Greenbrier Mall
Chesapeake Square Mall

Chesapeake Square Mall

You can find the perfect gifts to bring home at Chesapeake Square Mall during your trip to Chesapeake. Discover the top-notch restaurants and acclaimed theater scene in this family-friendly area.

Chesapeake Square Mall
Chesapeake Conference Center

Chesapeake Conference Center

After visiting Chesapeake Conference Center, make a plan to see the other sights and activities in Chesapeake. Experience the area's acclaimed theater scene and great live music.

Chesapeake Conference Center

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 $910. 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

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