Chesapeake Vacations 2026

Top Chesapeake hotels deals

Comfort Suites Chesapeake - Norfolk

1550 Crossways Blvd Chesapeake VA

Free cancellation

CA $126

CA $148 total

Sep 7 - Sep 8

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.

Wyndham Virginia Beach Oceanfront

5700 Atlantic Ave Virginia Beach VA

Free cancellation

Reserve now, pay when you stay

CA $131

CA $164 total

Aug 31 - Sep 1

includes taxes & fees

Stay at this hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Virginia Beach Boardwalk and Neptune Statue are located nearby.

Ocean Resort

Atlantic Avenue,2417 Virginia Beach VA

Free cancellation

Reserve now, pay when you stay

CA $116

CA $156 total

Sep 20 - Sep 21

includes taxes & fees

Stay at this hotel in Virginia Beach. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Virginia Beach Boardwalk and Pacific Avenue are located nearby.

Crowne Plaza Virginia Beach Town Center by IHG

4453 Bonney Rd Virginia Beach VA

Free cancellation

CA $128

CA $150 total

Sep 7 - Sep 8

includes taxes & fees

Book a stay at this business-friendly hotel in Virginia Beach. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Veterans United Home Loans Amphitheater at Virginia Beach and Norfolk Premium Outlets are located nearby.

Holiday Inn & Suites Virginia Beach North Beach by IHG

3900 Atlantic Avenue Virginia Beach VA

Free cancellation

CA $226

CA $262 total

Sep 20 - Sep 21

includes taxes & fees

Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, 3 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Virginia Beach Boardwalk and Neptune Statue are located nearby.

Pool

Free WiFi

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

1101 Atlantic Ave Virginia Beach VA

Free cancellation

CA $116

CA $136 total

Sep 20 - Sep 21

includes taxes & fees

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 Pacific Avenue 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.

Stay near popular Chesapeake attractions

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.

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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 . 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.