Chesapeake Vacation Packages 2026 from $228

Chesapeake flight + hotel vacation packages

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

John Yancey Oceanfront Inn

$228

per person

Dec 4 - Dec 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

The Historic Cavalier Hotel and Beach Club, Autograph Collection

Northeast Virginia Beach

$1,401

per person

Dec 30 - Jan 3

found 11 hours ago

Roundtrip non-stop flight included

Islip (ISP) to Norfolk (ORF)

A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the 24-hour gym and perks like a free beach shuttle.

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Northeast Virginia Beach

$638

per person

Dec 30 - Jan 3

found 11 hours ago

Roundtrip non-stop flight included

Islip (ISP) to Norfolk (ORF)

This aparthotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the hot tub and conveniences like a 24-hour front desk and laundry facilities.

The Barclay Towers Resort Hotel

Northeast Virginia Beach

$636

per person

Dec 30 - Jan 3

found 11 hours ago

Roundtrip non-stop flight included

Islip (ISP) to Norfolk (ORF)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the hot tub and conveniences like a 24-hour front desk and laundry facilities.

Sunrise Inn By OYO Newport News US-60

North Newport News

$592

per person

Dec 25 - Jan 1

found 19 hours ago

Roundtrip flight included

New York (NYC) to Norfolk (ORF)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Top Chesapeake hotels deals

Comfort Suites Chesapeake - Norfolk

1550 Crossways Blvd Chesapeake VA

Free Cancellation

$83 nightly

$98 total

Nov 15 - Nov 16

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.

YourSpace Hotels Chesapeake

2137 Starmount Parkway Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$88 nightly

$103 total

Nov 15 - Nov 16

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.

SpringHill Suites by Marriott Chesapeake Greenbrier

1446 Crossways Blvd Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$138 total

Nov 16 - Nov 17

Total with taxes and fees

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

Hyatt Studios Chesapeake

101 Volvo Parkway Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$99 total

Oct 18 - Oct 19

Total with taxes and fees

A 24-hour gym, free self parking, and laundry facilities are featured at this hotel. Enjoy the free on-the-go breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.

Aloft by Marriott Chesapeake

1454 Crossways Boulevard Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$125 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.

Hilton Vacation Club Ocean Beach Club Virginia Beach

3401 Atlantic Ave Virginia Beach VA

Free Cancellation

Reserve now, pay when you stay

$96 nightly

$113 total

Oct 22 - Oct 23

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.

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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 $228. 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.