Chesapeake Vacation Packages 2026 from $517

Chesapeake flight + hotel vacation packages

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

TRU by Hilton Chesapeake, VA

Greenbrier

$517

per person

Jun 27 - Jun 30

found 20 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

A gym is featured at this hotel, along with free self parking. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. A 24-hour business center, express check-in, and express check-out are also on offer.

The Ocean Key Virginia Beach Resort

Northeast Virginia Beach

Save 100% on your flight

$702

per person

Aug 10 - Aug 15

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

This aparthotel features an indoor pool, a gym, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A safe deposit box is provided and the front desk is staffed around-the-clock.

Sea Ranch Resort

$702

per person

Jun 27 - Jun 30

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Sea Scape Beach and Golf Villas

Sea Scape

$737

per person

Jul 26 - Jul 29

found 22 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

2 outdoor pools, an indoor pool, and an outdoor tennis court are all featured at this smoke-free condo. Bring the family and enjoy the mini golf, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Sanderling Resort Residences

Save 100% on your flight

$2,230

per person

Jun 27 - Jun 30

found 1 day ago

Roundtrip flight included

Boston (BOS) 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

$93 nightly

$109 total

May 31 - Jun 1

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.

STUDIOS & SUITES 4 LESS CHESAPEAKE

2222 S Military Hwy Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$70 nightly

$83 total

May 26 - May 27

Total with taxes and fees

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

YourSpace Hotels Chesapeake

2137 Starmount Parkway Chesapeake VA

$117 nightly

$136 total

May 31 - Jun 1

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.

TRU by Hilton Chesapeake, VA

1570 CROSSWAYS BLVD Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$112 nightly

$130 total

May 31 - Jun 1

Total with taxes and fees

Wyndham Virginia Beach Oceanfront

5700 Atlantic Ave Virginia Beach VA

Free Cancellation

Reserve now, pay when you stay

$104 nightly

$121 total

May 31 - Jun 1

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.

Hyatt Place Virginia Beach / Oceanfront

3601 ATLANTIC AVENUE Virginia Beach VA

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$196 total

May 31 - Jun 1

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.

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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.

Chesapeake Conference Center

After visiting Chesapeake Conference Center, make a plan to see the other sights and activities in Chesapeake. Experience the area's acclaimed theater scene and 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 $517. 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.