Chesapeake Vacation Packages 2026 from $449

Chesapeake flight + hotel vacation packages

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

Boardwalk Resort and Villas

Northeast Virginia Beach

$449

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Norfolk (ORF)

This hotel features an indoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A business center, express check-out, and laundry facilities are also on offer.

The Barclay Towers Resort Hotel

Northeast Virginia Beach

$503

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Chicago (ORD) 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.

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Northeast Virginia Beach

$498

per person

Oct 15 - Oct 18

found 1 day ago

Roundtrip flight included

Chicago (ORD) 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.

Chincoteague Bay RV Resort & Cottages

$472

per person

Oct 16 - Oct 20

found 21 hours ago

Roundtrip non-stop flight included

San Juan (SJU) to Norfolk (ORF)

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this vacation home. WiFi in public areas is free. A convenience store and a picnic area are also provided.

The Colony at Virginia Beach

Northeast Virginia Beach

$989

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Norfolk (ORF)

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this condo. WiFi in public areas is free. Barbecue grills are provided for your convenience.

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

Hyatt Studios Chesapeake

101 Volvo Parkway Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$167 total

Sep 13 - Sep 14

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.

Breakfast included

Pet friendly

YourSpace Hotels Chesapeake

2137 Starmount Parkway Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$109 total

Oct 12 - Oct 13

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

$94 nightly

$110 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

Holiday Inn & Suites Virginia Beach North Beach by IHG

3900 Atlantic Avenue Virginia Beach VA

Free Cancellation

$127 nightly

$148 total

Oct 11 - Oct 12

Total with taxes and fees

This smoke-free hotel features 3 restaurants, 3 outdoor pools, and an indoor pool. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a lazy river and a free kid's club, and families will appreciate the onsite laundry facilities.

Pool

Free WiFi

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

1101 Atlantic Ave Virginia Beach VA

Free Cancellation

$76 nightly

$89 total

Oct 4 - Oct 5

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

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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 building with a large arched entrance, surrounded by trees and a parking lot.

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.

See properties

Frequently asked questions

How much are vacation packages to Chesapeake?

Travelocity provides package deals to Chesapeake, including flights and hotels, from an impressive $449. 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.