Chesapeake Vacation Packages 2026 from $373

Chesapeake flight + hotel vacation packages

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

Pamlico Station Edgecamp

South Rodanthe

$373

per person

Feb 14 - Feb 16

found 8 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

This hotel features a hot tub and a sauna. Free self parking and concierge services are also offered on site.

Sanderling Resort Residences

Save 100% on your flight

$1,084

per person

Feb 14 - Feb 16

found 8 hours ago

Roundtrip non-stop 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.

The Sanderling

$712

per person

Mar 26 - Mar 29

found 13 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Boardwalk Resort and Villas

Northeast Virginia Beach

$562

per person

Apr 5 - Apr 10

found 1 day ago

Roundtrip non-stop flight included

Pittsburgh (PIT) 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 Ocean Key Virginia Beach Resort

Northeast Virginia Beach

$722

per person

Feb 13 - Feb 20

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 business center, laundry facilities, and free newspapers are also on offer.

Top Chesapeake hotels deals

Comfort Suites Chesapeake - Norfolk

1550 Crossways Blvd Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$70 nightly

$82 total

Jan 13 - Jan 14

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Pool

Breakfast included

Wingate by Wyndham Chesapeake

817 Greenbrier Circle Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$88 total

Jan 18 - Jan 19

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

Holiday Inn Express Chesapeake - Norfolk by IHG

721 Conference Center Drive Chesapeake VA

Free Cancellation

$83 nightly

$97 total

Jan 25 - Jan 26

Total with taxes and fees

This hotel features a gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A 24-hour business center, luggage storage, and laundry facilities are also on offer.

Pool

Breakfast included

TRU by Hilton Chesapeake, VA

1570 CROSSWAYS BLVD Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$110 total

Jan 18 - Jan 19

Total with taxes and fees

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.

Breakfast included

Pet friendly

Fairfield Inn and Suites By Marriott Chesapeake

1560 Crossways Blvd Chesapeake VA

$80 nightly

$94 total

Jan 18 - Jan 19

Total with taxes and fees

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

Pool

Breakfast included

WoodSpring Suites Chesapeake - Norfolk South

137 Kempsville Rd Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$69 nightly

$81 total

Jan 12 - Jan 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-out. Laundry facilities are provided for your convenience.

Pet friendly

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.

Popular places to visit

Greenbrier Mall

4/5(260 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(76 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 great live music and acclaimed theater scene.

Frequently asked questions

How much are vacation packages to Chesapeake?

Travelocity provides package deals to Chesapeake, including flights and hotels, from an impressive $373. 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.