Chesapeake Vacation Packages 2025/2026 from $305

Chesapeake flight + hotel vacation packages

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

Delta Hotels by Marriott Virginia Beach Waterfront Suites

Northeast Virginia Beach

$305

per person

Jan 27 - Jan 31

found 15 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

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 conveniences like a 24-hour front desk and laundry facilities.

Pamlico Station Edgecamp

$488

per person

Jan 16 - Jan 19

found 14 hours ago

Roundtrip flight included

Chicago (ORD) to Norfolk (ORF)

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

The Sanderling

$694

per person

Dec 26 - Dec 29

found 1 day ago

Roundtrip non-stop flight included

Chicago (MDW) 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.

Residence Inn by Marriott Norfolk Airport

$348

per person

Jan 27 - Jan 31

found 15 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free buffet breakfast is served.

TRU by Hilton Chesapeake, VA

Greenbrier East

$315

per person

Jan 27 - Jan 31

found 15 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.

Top Chesapeake hotels deals

Comfort Suites Chesapeake - Norfolk

1550 Crossways Blvd Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$79 nightly

$93 total

Nov 24 - Nov 25

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

Red Roof Inn Chesapeake Conference Center

724 Woodlake Dr Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$88 total

Nov 23 - Nov 24

Total with taxes and fees

Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. A snack bar/deli is also provided.

Pet friendly

Parking included

Wingate by Wyndham Chesapeake

817 Greenbrier Circle Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$79 nightly

$93 total

Nov 30 - Dec 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.

Pool

Hot Tub

Aloft Chesapeake

1454 Crossways Boulevard Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$102 total

Dec 7 - Dec 8

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.

Pool

Pet friendly

STUDIOS & SUITES 4 LESS CHESAPEAKE

2222 S Military Hwy Chesapeake VA

Free Cancellation

Reserve now, pay when you stay

$61 nightly

$73 total

Nov 20 - Nov 21

Total with taxes and fees

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.

Parking included

Free WiFi

Holiday Inn Express Chesapeake - Norfolk by IHG

721 Conference Center Drive Chesapeake VA

Free Cancellation

$87 nightly

$102 total

Nov 23 - Nov 24

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

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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 $305. 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.