Chesapeake Vacation Packages 2026 from $665

Chesapeake flight + hotel vacation packages

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

Sea Ranch Resort

Save 100% on your flight

$665

per person

Aug 19 - Aug 24

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

The Burrus House Inn Waterfront Suites

Save 100% on your flight

$944

per person

Aug 19 - Aug 24

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)

This bed & breakfast features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. A snack bar/deli, express check-in, and express check-out are also on offer.

John Yancey Oceanfront Inn

Save 100% on your flight

$800

per person

Aug 19 - Aug 24

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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 Sanderling

Save 100% on your flight

$1,229

per person

Aug 19 - Aug 24

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)

A full-service spa, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. Enjoy the 2 hot tubs and perks like free WiFi.

Sanderling Resort Residences

Save 100% on your flight

$1,879

per person

Jul 17 - Jul 19

found 1 day ago

Roundtrip non-stop flight included

Islip (ISP) to Norfolk (ORF)

A full-service spa, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free resort. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. Family-friendly amenities include a children's pool and kid-friendly dining, along with kayaking.

Top Chesapeake hotels deals

Wingate by Wyndham Chesapeake

817 Greenbrier Circle Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$123 total

Jun 14 - Jun 15

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.

Pool

Hot Tub

STUDIOS & SUITES 4 LESS CHESAPEAKE

2222 S Military Hwy Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$70 nightly

$83 total

Jun 4 - Jun 5

Total with taxes and fees

Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.

Parking included

Free WiFi

YourSpace Hotels Chesapeake

2137 Starmount Parkway Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$113 nightly

$131 total

Jun 21 - Jun 22

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

$106 nightly

$124 total

Jun 10 - Jun 11

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

Hyatt Place Virginia Beach / Oceanfront

3601 ATLANTIC AVENUE Virginia Beach VA

Free Cancellation

Reserve now, pay when you stay

$279 nightly

$323 total

Jun 4 - Jun 5

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the seasonal outdoor pool and free buffet breakfast each morning.

Pool

Breakfast included

Hilton Virginia Beach Oceanfront

3001 Atlantic Ave Virginia Beach VA

Free Cancellation

Reserve now, pay when you stay

$229 nightly

$266 total

Jun 7 - Jun 8

Total with taxes and fees

This resort features 3 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's an indoor pool on site, and a 24-hour front desk and a rooftop terrace 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.

Popular places to visit

Greenbrier Mall

4/5(263 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

4/5(78 reviews)

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.

This is a new bridge over the indian creek in Chesapeake virginia. Near northwest river campground

Chesapeake City Park

5/5(1 review)

Chesapeake City Park is just one of the places to see in Chesapeake, so why not enjoy the other things to explore during your travels? Stroll along the area's beautiful beaches or experience its great live music.

Frequently asked questions

How much are vacation packages to Chesapeake?

Travelocity provides package deals to Chesapeake, including flights and hotels, from an impressive $665. 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.