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

YourSpace Hotels Chesapeake

YourSpace Hotels Chesapeake

3 out of 5
2137 Starmount Parkway Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is NZ$233 per night from 21 June to 22 June
NZ$233
21 June - 22 June
includes taxes & fees
Stay at this business-friendly hotel in Chesapeake. Enjoy free Wi-Fi, free parking and a 24-hour fitness centre. Popular attractions Chesapeake Square Mall and ...
"Staff is excellent! Safety is good. Property already needs repairs. Water leaking around light in the shower. Room above not in use. Hot water took 20 minutes to warm the shower or reach kitchen sink. Rooms looked clean but, Found trash behind a dresser. Sticky spots on counters and in drawers next ..."

Reviewed on 3 June 2026

Opens in a new windowYourSpace Hotels Chesapeake
Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd Chesapeake VA
Fully refundable
The price is NZ$270 per night from 28 June to 29 June
NZ$270
28 June - 29 June
includes taxes & fees
Stay at this business-friendly hotel in Chesapeake. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
"The property was clean. Not exceptional. Staff helpful. Breakfast not the greatest. The stay was nice but for the price they need to upgrade. Carpet definitely needs to be changed."

Reviewed on 14 June 2026

Opens in a new windowComfort Suites Chesapeake - Norfolk
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 NZ$218 per night from 5 July to 6 July
NZ$218
5 July - 6 July
includes taxes & fees
Stay at this business-friendly hotel in Chesapeake. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
"This hotel is run down, there was 0 hot water and when I asked the front desk he said oh yeah the water heater has been broke for 2 days - you fail to mention this to your customers??? The room was dark and old and very noisy. The entire floor smelled like marijuana. It was so bad I checked out before ..."

Reviewed on 15 June 2026

Opens in a new windowWingate by Wyndham 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.

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