Chesapeake Holiday Packages

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Top Chesapeake holiday packages

Price found within the past 48 hours. Click for updated prices.
The Ocean Key Virginia Beach Resort
The Barclay Towers Resort Hotel
The Colony at Virginia Beach
Delta Hotels by Marriott Virginia Beach Waterfront Suites
Holiday Inn Express & Suites VA Beach Oceanfront by IHG

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

Hyatt Studios Chesapeake

Hyatt Studios Chesapeake

2 out of 5
101 Volvo Parkway Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is AU$209 per night from 16 Aug to 17 Aug
AU$209
16 Aug - 17 Aug
includes taxes & fees
Hyatt Studios Chesapeake: Pet-friendly hotel with free breakfast and free WiFi.
"This place was very clean and. Modern I loved the kitchenette in the room and will be staying here on my next trip to Virginia"

Reviewed on 8 Aug 2026

Opens in a new windowHyatt Studios Chesapeake
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
The price is AU$155 per night from 31 Aug to 1 Sept
AU$155
31 Aug - 1 Sept
includes taxes & fees
Wyndham Virginia Beach Oceanfront: Pet-friendly hotel with free WiFi and free parking. Located by the ocean.
"Everything was great!"

Reviewed on 8 Aug 2026

Opens in a new windowWyndham Virginia Beach Oceanfront
Ocean Resort

Ocean Resort

2.5 out of 5
Atlantic Avenue,2417 Virginia Beach VA
Fully refundableReserve now, pay when you stay
The price is AU$174 per night from 7 Sept to 8 Sept
AU$174
7 Sept - 8 Sept
includes taxes & fees
Ocean Resort: Hotel with free WiFi and free parking. Located on the boardwalk.
"The location was wonderful as well as the staff. The parking was horrible!!! People did smoke on the balconies and since there is no wall between them it comes on over to the next balcony big time !! Something was leaking above my balcony and splattering on me when I sat out there."

Reviewed on 9 Aug 2026

Opens in a new windowOcean Resort
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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.