Cheap Vacations in Chesapeake

Choose two or more items and save on your trip:

3-night Chesapeake vacations

Price found within the past 48 hours. Click for updated prices.
Beach Quarters Resort
The Inn at Four Eleven York
Delta Hotels by Marriott Virginia Beach Waterfront
Hilton Norfolk The Main
Wyndham Garden Norfolk Downtown
Hilton Vacation Club Oceanaire Virginia Beach
La Quinta Inn & Suites by Wyndham Norfolk
White Marlin Inn
Hilton Vacation Club Ocean Beach Club Virginia Beach
Travelodge by Wyndham Virginia Beach Bay Beach
Days Inn by Wyndham Chesapeake
Surry Seafood Company

4-night Chesapeake vacations

Price found within the past 48 hours. Click for updated prices.
Hilton Vacation Club Ocean Beach Club Virginia Beach
Boardwalk Resort and Villas
Four Sails Resort
Beach Quarters Resort
Delta Hotels by Marriott Virginia Beach Waterfront
Hilton Garden Inn Virginia Beach Town Center
The Capes Hotel
Hilton Garden Inn Virginia Beach Oceanfront
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
The Ocean Key Resort by VSA Resorts
Hilton Vacation Club Oceanaire Virginia Beach
Wyndham Virginia Beach Oceanfront

6-7 night Chesapeake vacations

Price found within the past 48 hours. Click for updated prices.
Outer Banks Inn
Sanderling Resort
Four Sails Resort
Boardwalk Resort and Villas
Delta Hotels by Marriott Virginia Beach Waterfront
Beach Quarters Resort
John Yancey Oceanfront Inn
The Capes Hotel
Hilton Garden Inn Virginia Beach Town Center
Hilton Vacation Club Ocean Beach Club Virginia Beach
Homewood Suites by Hilton Virginia Beach/Norfolk Airport
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

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

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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com 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.