Deals on vacations and trips to Chesapeake, VA

Save when you book Chesapeake, VA package deals

Choose two or more items and save on your trip:
Choose two or more items and save on your trip:

Chesapeake flight + hotel vacation packages

Beachwoods by Diamond Resorts
Owens' Motel
Roanoke Island Inn
Fin 'n Feather Waterside Inn By Kees Vacations
Oceanside Court by Kees Vacations

Top Chesapeake hotels deals

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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.

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Frequently asked questions

How much are vacation packages to Chesapeake?
With deals starting at just $484, hotel and flight packages are the perfect way to make your vacation budget stretch further. Watch out Chesapeake — here you come!
How long should my Chesapeake vacation be?
Around 2 nights is the average amount of time visitors vacation in Chesapeake. But the ideal trip length comes down to how many treasured memories you want to create. Why not allow a little more time and discover some off-the-beaten-path gems?
Where can I get the best vacation package deals for Chesapeake?
There are amazing Chesapeake package deals to be gained with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties across the globe? Keep that in mind the next time you’re ready to tick another destination off your must-see list.
Why should I purchase my Chesapeake vacation bundle via Travelocity?
Because you’ll never roam alone if you book through us, and we offer round-the-clock support and superb service to boot. Add to that our Price Match Guarantee and a massive range of destinations to choose from. It’s our job to help you jet off on the vacation of a lifetime.
Will I save money on my Chesapeake car rental if I combine it with a hotel or flight?
Absolutely — combine your car, flight and hotel into a Chesapeake vacation package and you can save a handsome sum. With so many things to do in the Chesapeake area, that set of wheels will make it easy to explore. Once you’re behind the wheel, hit the wide open road and find your way to Busch Gardens Williamsburg, an unmissable sight about 40 mi from Chesapeake.
What is the best time of year to go to Chesapeake?
Visit in if you don’t want to miss a thing. While they are the busiest few months, the buzzing vibe associated with peak season is part of the charm. If you’re looking for a slower pace, may fit your plans better. Don’t want to fork out for somewhere to stay? Hold off on booking in , when rates usually soar. Search for someplace more affordable in instead.
Which airport is best for Chesapeake?
Many vacationers arrive at Norfolk Intl. Airport (ORF). Once you’ve touched down and collected your luggage, make tracks 10 mi southwest to reach inner Chesapeake. Newport News - Williamsburg Intl. Airport (PHF) is the other option available, 30 mi from the city center.
What is there to do in Chesapeake?
While venturing off the beaten track is no doubt rewarding, you shouldn’t ignore the well-known sights that make a destination famous. Greenbrier Mall and Chesapeake Square Mall are a couple of them in Chesapeake.
Where should I stay when visiting Chesapeake?
Many travelers hit the hay at the Holiday Inn Express Chesapeake - Norfolk, an IHG Hotel. It’s the perfect base for your Chesapeake vacation.
Can I go on vacation to Chesapeake at this time?
Travelocity has all the knowledge to ensure your getaway dreams a reality, so before arranging a ticket to Chesapeake, look over our Covid-19 Travel Advisor. Here you’ll find all the up-to-date info on quarantine policies, travel restrictions and much more.