Chesapeake Vacation Packages 2026 from $590

Chesapeake flight + hotel vacation packages

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

Sea Ranch Resort

$590

per person

Oct 22 - Oct 29

found 1 day ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Norfolk (ORF)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference center. Enjoy the gym and perks like free self parking.

John Yancey Oceanfront Inn

Save 100% on your flight

$599

per person

Oct 22 - Oct 29

found 1 day ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Norfolk (ORF)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Families will appreciate the playground and barbecue grills. There's an outdoor pool on site, and a terrace and a picnic area are also provided.

Blackbeard's Lodge

$787

per person

Oct 22 - Oct 29

found 1 day ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Norfolk (ORF)

A seasonal outdoor pool, free self parking, and barbecue grills are featured at this hotel. Guests will appreciate perks like free WiFi and a free airport shuttle. A picnic area and luggage storage are also provided.

Pony Island Inn

$863

per person

Oct 22 - Oct 29

found 1 day ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Norfolk (ORF)

A seasonal outdoor pool, free self parking, and barbecue grills are featured at this motel. WiFi in public areas is free. A picnic area is also provided.

Roanoke Island Inn

Historic Downtown Manteo

Save 100% on your flight

$1,187

per person

Oct 22 - Oct 29

found 1 day ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Norfolk (ORF)

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A garden, a snack bar/deli, and a picnic area are also on offer.

Top Chesapeake hotels deals

Comfort Suites Chesapeake - Norfolk

1550 Crossways Blvd Chesapeake VA

Free Cancellation

$95 nightly

$111 total

Oct 4 - Oct 5

Total with taxes and fees

This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

YourSpace Hotels Chesapeake

2137 Starmount Parkway Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$92 nightly

$108 total

Sep 27 - Sep 28

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-in. A 24-hour gym and locker space are also provided.

Pet friendly

Parking included

Wyndham Virginia Beach Oceanfront

5700 Atlantic Ave Virginia Beach VA

Free Cancellation

Reserve now, pay when you stay

$82 nightly

$96 total

Oct 4 - Oct 5

Total with taxes and fees

This hotel features an indoor pool, a gym, and a restaurant. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A bar/lounge, a 24-hour front desk, and a terrace are also provided.

Pool

Pet friendly

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

1801 Atlantic Ave Virginia Beach VA

Free Cancellation

$119 nightly

$139 total

Sep 28 - Sep 29

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free on-the-go breakfast each morning.

Pool

Breakfast included

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

1101 Atlantic Ave Virginia Beach VA

Free Cancellation

$76 nightly

$89 total

Oct 13 - Oct 14

Total with taxes and fees

This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Free self parking, a library, and dry cleaning are also offered.

Pool

Parking included

Hilton Vacation Club Ocean Beach Club Virginia Beach

3401 Atlantic Ave Virginia Beach VA

Free Cancellation

Reserve now, pay when you stay

$92 nightly

$108 total

Sep 24 - Sep 25

Total with taxes and fees

This smoke-free hotel features 2 indoor pools, an outdoor pool, and a restaurant. Enjoy the 24-hour gym and perks like free WiFi. There's a beach bar on site, and laundry facilities and concierge services are also provided.

Pool

Free WiFi

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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.

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Frequently asked questions

How much are vacation packages to Chesapeake?

Travelocity provides package deals to Chesapeake, including flights and hotels, from an impressive $590. 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 40 mi 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 10 mi southwest to reach central Chesapeake. Newport News - Williamsburg Intl. Airport (PHF) is another option, 30 mi 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.