Chesapeake Holiday Packages

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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

Schooner Inn

Schooner Inn

2 out of 5
215 Atlantic Ave, Virginia Beach, VA
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the convenient ...
"I have visited hundreds of times. That speaks for itself."

Reviewed on 10 Sept 2025

Opens in a new windowSchooner Inn
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave, Virginia Beach, VA
The price is NZ$190 per night from 22 Sept to 23 Sept
NZ$190
22 Sept - 23 Sept
includes taxes & fees
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff ...
"The beach was beautiful and I walked out of my room to see the ocean.."

Reviewed on 8 Sept 2025

Opens in a new windowWyndham Virginia Beach Oceanfront
STUDIOS & SUITES 4 LESS CHESAPEAKE

STUDIOS & SUITES 4 LESS CHESAPEAKE

2 out of 5
2222 S Military Hwy, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is NZ$105 per night from 17 Sept to 18 Sept
NZ$105
17 Sept - 18 Sept
includes taxes & fees
Stay at this hotel in Chesapeake. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
"The staff was very accommodating."

Reviewed on 9 Sept 2025

Opens in a new windowSTUDIOS & SUITES 4 LESS CHESAPEAKE
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