Cheap Vacations in Chesapeake

Choose two or more items and save on your trip:

4-night Chesapeake vacations

The Inn at Four Eleven York
Hilton Virginia Beach Oceanfront

Chesapeake Vacation Deal FAQ's

Where to find Chesapeake package deals?

On CheapTickets, you can find package deals in Chesapeake and save up to $287.

When is peak season in Chesapeake?

are very popular times to visit Chesapeake.

When is the best time to visit Chesapeake?

If you're looking for cheap vacations to Chesapeake, is the best time to visit Chesapeake.

When is the worst time time to visit Chesapeake?

Prices for Chesapeake vacations can peak during .

When is low season in Chesapeake?

We have found to be the least-crowded time of the year to visit Chesapeake.

Where is Chesapeake?

Are you searching for a real steal? You're in the right place! Your next fabulous adventure awaits in Chesapeake.

Where is Chesapeake?

It's a neighborhood of Norfolk - Virginia Beach. You'll discover it 10 miles south of the downtown area.

Cheap Things to do in Chesapeake

Forget about entry fees, ticket prices and costly days out! With our list of free things to see in or near Chesapeake, you'll be ahead of the crowd with some of the best free travel hacks:

  • Have a look at the displays, check for one-off events and exercise your brain (without spending a cent) at the Douglas MacArthur Memorial, the Hampton Roads Naval Museum and the Portlock Galleries at SoNo.
  • Keep an eye out for the exciting things going on at the D'Art Center. This fine establishment is well known for coordinating some of the most interesting free culture and arts events around. Have a look at the upcoming program and see what interests you.
  • Crush boredom without ruining your budget at Oak Grove Lake Park. It ought to be the first place you visit if you're in the mood for some outdoor excitement.
  • Frugal history fans should really add the Norfolk State University, the Chesapeake Veterans' Memorial, the Armed Forces Memorial and Hill House Museum to their vacation to-do lists. These age-old landmarks also provide outstanding photo opportunities!
  • If you're in the area, we recommend dropping by the Chesapeake Central Library.
  • See if it's possible to get a peek inside St. Paul's Episcopal Church. If not, it's still worth discovering from the outside — there's always something uplifting about being in the presence of religious landmarks.

Cheap Chesapeake Vacation Package Deals

Remember, at CheapTickets cheap really doesn't have to mean nasty. Even though we're wildly economical, we definitely will not make trade-offs on quality or comfort.

Want a world of options on accommodations and flights? Our 500 partner airlines and 500,000 global properties offer plenty of choice. You can also save as much as $287 when you combine your bookings into a package.

Let your inner penny-pincher book without a worry with our Price Guarantee. Here's how it works — if within 48 hours you come across your vacation deal at a better price, we will match it and reimburse the difference. After all, frugal is our middle name!

Get CheapCash

Book your flights, earn CheapCash and use it on your next qualifying CheapTickets hotel reservation. Our rewards program is as straightforward as that. So, what are you waiting around for?

Taking advantage of our CheapCash rewards program couldn't get much easier. Log in to your existing account or sign up (for free!), and you'll be able to save on eligible bookings, as well as getting intel on other fantastically-thrifty bonus offers and super-scrimpy perks!

Cheap Car Rentals in Chesapeake

We hear you — you've already had to part with enough of your hard-earned dough on your getaway, so you have no interest in spending a fortune on cabs. Fortunately, Chesapeake has a number of car rental places which should ease the burden on your bank account.

Cheap Hotels in Chesapeake

Choose from 44 hotels just a short commute from the heart of Chesapeake. While you won't find accommodation options in the center, you will find an amazing deal!

We suggest the Econo Lodge Chesapeake and the WoodSpring Suites Chesapeake-Norfolk Greenbrier. They're located at 2222 S Military Hwy, Chesapeake 23320, VA and 1708 Sentinel Drive, Chesapeake 23320, VA, respectively.

Flight deals to Chesapeake

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Top rated hotels for your Chesapeake vacation

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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.

^Savings based on all package bookings with Flight + Hotel made on from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.