Chesapeake Vacations 2025 from CA $592

Chesapeake flight + hotel packages

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

Ocean Pines Resort by Capital Vacations

per person

Mar. 28 - Mar. 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Norfolk (ORF)

Stay at this 3.5-star beach vacation home in Kitty Hawk. Enjoy free WiFi, free parking, and a beach locale. Popular attractions The Sanderling Spa and Nor'Banks Sailing are located nearby.

Boardwalk Resort and Villas

Northeast Virginia Beach

per person

Mar. 21 - Mar. 27

found 9 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Norfolk (ORF)

Stay at this 3-star beach hotel in Virginia Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Virginia Beach Boardwalk and Atlantic Fun Park are located nearby.

Beach Quarters Resort

Northeast Virginia Beach

per person

Mar. 21 - Mar. 27

found 9 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Norfolk (ORF)

Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Virginia Beach Boardwalk and Sandbridge Beach are located nearby.

Four Sails Resort

Northeast Virginia Beach

per person

Mar. 21 - Mar. 27

found 9 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Norfolk (ORF)

Stay at this 3.5-star beach condo in Virginia Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Virginia Beach Boardwalk and Neptune Statue are located nearby.

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Northeast Virginia Beach

per person

Mar. 21 - Mar. 27

found 9 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Norfolk (ORF)

Stay at this 3-star beach aparthotel in Virginia Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Virginia Beach Boardwalk and Virginia Beach Fishing Pier are located nearby.

Top Chesapeake hotels deals

Quality Inn

100 Red Cedar Court, Chesapeake, VA

Free cancellation

Reserve now, pay when you stay

CA $65

CA $79 total

includes taxes & fees

23 Feb - 24 Feb

Book a stay at this business-friendly hotel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Greenbrier Mall and Waterside District are located nearby.

Wingate by Wyndham Chesapeake

817 Greenbrier Circle, Chesapeake, VA

Free cancellation

Reserve now, pay when you stay

CA $119

CA $139 total

includes taxes & fees

2 Mar - 3 Mar

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 Waterside District are located nearby.

Pool

Hot tub

Aloft Chesapeake

1454 Crossways Boulevard, Chesapeake, VA

Free cancellation

Reserve now, pay when you stay

CA $129

CA $150 total

includes taxes & fees

9 Feb - 10 Feb

Stay at this 3-star 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.

SpringHill Suites by Marriott Chesapeake Greenbrier

1446 Crossways Blvd, Chesapeake, VA

Free cancellation

Reserve now, pay when you stay

CA $124

CA $144 total

includes taxes & fees

9 Feb - 10 Feb

Stay at this 3-star 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.

Hilton Vacation Club Oceanaire Virginia Beach

3421 Atlantic Ave, Virginia Beach, VA

Free cancellation

Reserve now, pay when you stay

CA $135

CA $203 total

includes taxes & fees

12 Feb - 13 Feb

Stay at this 3.5-star beach hotel in Virginia Beach. Enjoy free WiFi, a beach locale, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Virginia Beach Boardwalk and Neptune Statue are located nearby.

Hyatt Place Virginia Beach / Oceanfront

3601 ATLANTIC AVENUE, 36TH AND ATLANTIC, Virginia Beach, VA

Free cancellation

Reserve now, pay when you stay

CA $115

CA $135 total

includes taxes & fees

12 Feb - 13 Feb

Stay at this 3-star beach hotel in Virginia Beach. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Virginia Beach Boardwalk and Neptune Statue 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

3.5/5(4 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.

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 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 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 $592. 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.