Chesapeake Vacation Packages 2025/2026 from $333

Chesapeake flight + hotel vacation packages

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

Beach Quarters Resort

Northeast Virginia Beach

per person

Oct 31 - Nov 3

found 18 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

This hotel features an indoor pool and a gym. Enjoy the outdoor tennis court and perks like free WiFi. There's a seasonal outdoor pool on site, and a 24-hour front desk and a rooftop terrace are also provided.

Boardwalk Resort and Villas

Northeast Virginia Beach

Save 100% on your flight

per person

Oct 12 - Oct 16

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Sonesta Simply Suites Hampton

per person

Oct 20 - Oct 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

A 24-hour gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Business travelers can take advantage of the laundry service.

The Lodge at Kiln Creek Resort

Central Newport News

per person

Oct 20 - Oct 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

This Art Deco hotel features a golf course, 6 outdoor tennis courts, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.

Four Sails Resort

Northeast Virginia Beach

per person

Oct 20 - Oct 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

This condo resort features an indoor pool, a gym, and a restaurant. Enjoy the sauna and perks like free self parking and free WiFi. A picnic area and laundry facilities are also provided.

Top Chesapeake hotels deals

STUDIOS & SUITES 4 LESS CHESAPEAKE

2222 S Military Hwy, Chesapeake, VA

Free Cancellation

Reserve now, pay when you stay

$59 nightly

$69 total

Aug 18 - Aug 19

Total includes 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

Red Roof Inn Chesapeake Conference Center

724 Woodlake Dr, Chesapeake, VA

Free Cancellation

Reserve now, pay when you stay

$85 nightly

$99 total

Aug 21 - Aug 22

Total includes 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

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection

1101 Atlantic Ave, Virginia Beach, VA

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$118 total

Sep 14 - Sep 15

Total includes taxes and fees

This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Guests will appreciate free perks like free self parking and WiFi in public areas.

Pool

Parking included

Holiday Inn & Suites Virginia Beach North Beach by IHG

3900 Atlantic Avenue, Virginia Beach, VA

Free Cancellation

$161 nightly

$187 total

Sep 14 - Sep 15

Total includes 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

Hot Tub

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA

1801 Atlantic Ave, Virginia Beach, VA

Free Cancellation

$128 nightly

$149 total

Sep 1 - Sep 2

Total includes taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free on-the-go breakfast each morning.

Pool

Breakfast included

Oceans 2700

2700 Pacific Avenue, Virginia Beach, VA

Free Cancellation

Reserve now, pay when you stay

$76 nightly

$89 total

Sep 1 - Sep 2

Total includes taxes and fees

A seasonal outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.

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.

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 $333. 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.