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

TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
1570 CROSSWAYS BLVD Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 17 May to 18 May
AU$186
17 May - 18 May
includes taxes & fees
TRU by Hilton Chesapeake, VA: Pet-friendly hotel with free breakfast and free WiFi. Guests love the helpful staff!
Everything was great I love the pancake maker

Reviewed on 9 May 2026

Opens in a new windowTRU by Hilton Chesapeake, VA
Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

3 out of 5
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is AU$150 per night from 31 May to 1 June
AU$150
31 May - 1 June
includes taxes & fees
Wingate by Wyndham Chesapeake: Business-friendly hotel with free breakfast and free WiFi. Located in the business district.
Breakfast should be at least until 11. In the bathtub, there should be a mat or bathmats inside the bathtub, as the bathtub was extremely slippery.

Reviewed on 10 May 2026

Opens in a new windowWingate by Wyndham Chesapeake
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 AU$103 per night from 11 May to 12 May
AU$103
11 May - 12 May
includes taxes & fees
STUDIOS & SUITES 4 LESS CHESAPEAKE : Hotel with free WiFi and free parking. Guests love the helpful staff!
very clean and friendly employee

Reviewed on 9 May 2026

Opens in a new windowSTUDIOS & SUITES 4 LESS CHESAPEAKE
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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.