Chesapeake Vacation Packages 2025 from $590

Chesapeake flight + hotel vacation packages

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

Four Sails Resort

Northeast Virginia Beach

Save 100% on your flight

per person

Aug 22 - Aug 26

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.

John Yancey Oceanfront Inn

Save 100% on your flight

per person

Jul 31 - Aug 5

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Pamlico Station Edgecamp

Save 100% on your flight

per person

Jul 31 - Aug 4

found 24 hours ago

Roundtrip 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.

Sea Ranch Resort

Save 100% on your flight

per person

Jul 31 - Aug 5

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.

Ocean Pines Resort

Save 100% on your flight

per person

Aug 4 - Aug 9

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

This vacation home features an indoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Guests will appreciate free perks like free self parking and WiFi in public areas.

Top Chesapeake hotels deals

Wingate by Wyndham Chesapeake

817 Greenbrier Circle, Chesapeake, VA

Free Cancellation

Reserve now, pay when you stay

Get rates

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

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection

1101 Atlantic Ave, Virginia Beach, VA

Free Cancellation

Reserve now, pay when you stay

Get rates

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

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

1801 Atlantic Ave, Virginia Beach, VA

Free Cancellation

Reserve now, pay when you stay

Get rates

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

Schooner Inn

215 Atlantic Ave, Virginia Beach, VA

Get rates

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A safe deposit box is provided and the front desk is staffed around-the-clock.

Pool

Parking included

Delta Hotels by Marriott Virginia Beach Waterfront

2800 Shore Drive, Virginia Beach, VA

Free Cancellation

Reserve now, pay when you stay

Get rates

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.

Pool

Pet friendly

Wyndham Virginia Beach Oceanfront

5700 Atlantic Ave, Virginia Beach, VA

Free Cancellation

Reserve now, pay when you stay

Get rates

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

Don't see what you're looking for?

See all available properties in Chesapeake

View all properties

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 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 $590. 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.