Chesapeake Holiday Packages

Save when you book Chesapeake package deals

Choose two or more items and save on your trip:

Book your Chesapeake holiday

Holidays To Chesapeake

Looking to spend your annual leave somewhere with great scenery, a bustling city nightlife, country byways and loads of outdoor activities?

How about museums and historical sites? We'll even throw in the Atlantic Ocean, to boot—you just have to head to Chesapeake, Virginia. Between the surprises at Colonial Williamsburg to the shopping at Antique Alley, Chesapeake is the greatest getaway you've never heard of—until now!

Things to Do in Chesapeake

Your Chesapeake holiday kicks off on the Atlantic coast, about 320 kilometres south of Washington, D.C. It's as far south in Virginia as you can go before you hit North Carolina, and it’s one of the oldest areas of the original colonies in the United States. Get a real taste of early American life by checking out historic sites like nearby Chippokes Plantation or that granddaddy of all living history museums, Colonial Williamsburg.

Chesapeake also has heaps of places for nature buffs to take a hike or do some birdwatching. Despite its name, Dismal Swamp is great! Feel like a trip to the seashore? Of course you do. Book one of Wotif’s Chesapeake car hire options and cruise on over to the Atlantic to Virginia Beach quicker than you can say "Pass the sunscreen."

Shopping, Dining & Nightlife

If you’re into history, you’re in luck. Chesapeake is packed with antique shops—they even have antique malls, with rows upon rows of stalls selling everything from pieces of shipwrecks and sea glass to retro clothes and street signs. "Antique Alley" at Military Highway and Canal Street is a great place to get started. There are also modern shopping centres galore in the city. Don’t worry about your wallet our Chesapeake deals will save you enough cash to shop until you drop at the Chesapeake Square Mall.

Many of the restaurants here are also located in gigantic malls and shopping centres, so stow your bags at your hotel and start eating. When you're this close to the Atlantic, seafood is the way to go, and you can't go wrong by choosing one of several eateries named in honour of the area's history of swashbucklers and pirates. Chesapeake holidays practically require you to try the traditional crab cakes—no claw cracking required!

Hey, sailor! When you're done filling up on dinner, the nightlife in Chesapeake and nearby Norfolk is hopping, in no small part thanks to the naval base there. The most happening spots are near the harbour in Norfolk. From sipping a beer on a waterside deck, to jamming to ’80s nights, to trying country line dancing at a club, you're bound to find a place that speaks (or sings!) to you.

What's Next?

Chesapeake holiday packages don't have to be expensive when you let Wotif find your deals. Trust us to get you a bargain on Chesapeake packages alone, or extend your getaway by booking one of our Washington, D.C. holidays. What’s better than a relaxing road trip along the Eastern Seaboard, followed by an exciting adventure in the capital? Not much. Book today and kick off your trip tomorrow!

Top Chesapeake hotels

SpringHill Suites by Marriott Chesapeake Greenbrier

SpringHill Suites by Marriott Chesapeake Greenbrier

3 out of 5
1446 Crossways Blvd, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is NZ$181 per night from 16 Mar to 17 Mar
NZ$181
includes taxes & fees
16 Mar - 17 Mar
Stay at this 3-star business-friendly hotel in Chesapeake. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff and the ...
"The Hotel Staff"

Reviewed on 24 Feb. 2025

SpringHill Suites by Marriott Chesapeake Greenbrier
Aloft Chesapeake

Aloft Chesapeake

3 out of 5
1454 Crossways Boulevard, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is NZ$180 per night from 2 Mar to 3 Mar
NZ$180
includes taxes & fees
2 Mar - 3 Mar
Stay at this 3-star business-friendly hotel in Chesapeake. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
"Just what was needed!"

Reviewed on 22 Feb. 2025

Aloft Chesapeake
Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

2.5 out of 5
817 Greenbrier Circle, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is NZ$154 per night from 5 Mar to 6 Mar
NZ$154
includes taxes & fees
5 Mar - 6 Mar
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
"The hot tub and heated pool year round is the reason we come. The staff is okay, not the friendliest... The room is okay, some have a little wear and tear. Breakfast is bomb too! 👌😁Usually eggs, biscuits and gravy, waffles you make yourself, cereal, bagels, and fruit. Solid 4."

Reviewed on 21 Feb. 2025

Wingate by Wyndham Chesapeake
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.