Chesapeake Holidays

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Your Chesapeake Holiday

Pick a Chesapeake holiday package and you can prioritize what matters — enjoying yourself. No more planning hassles, just more free time to immerse yourself in the delights of this fascinating city, such as its rich history and family-friendly attractions. Eager to get out and explore? Greenbrier Mall, Chesapeake City Park and Chesapeake City Hall are just three of the most popular places to visit during a trip to Chesapeake. No matter your travel plans or the size of your budget, organising your ultimate tailored Chesapeake holiday is simple with Expedia.

Our guide on where to stay in Chesapeake

Find the best Chesapeake areas and neighborhoods for the activities you enjoy most. Learn more about Chesapeake

Chesapeake Holiday

Chesapeake Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Norfolk Intl. Airport (ORF)
Population
235,400
Max Temp Winter
10ºC
Max Temp Summer
29ºC
Top Sights
Jillians Billiards, Portlock Galleries at SoNo and Chesapeake City Park

Our pick of the best Chesapeake Hotel Deals

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 AU$136 per night from 26 Apr to 27 Apr
AU$136
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (1,015 reviews)
It was a quiet clean hotel. We stayed 1 night. The breakfast was hot and fresh.

Reviewed on 12 Apr 2026

Wingate by Wyndham Chesapeake
Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd Chesapeake VA
Fully refundable
The price is AU$174 per night from 26 Apr to 27 Apr
AU$174
26 Apr - 27 Apr
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
Need better breakfast. Bacon perhaps. Bolled eggs,

Reviewed on 11 Apr 2026

Comfort Suites Chesapeake - Norfolk
Holiday Inn Express Chesapeake - Norfolk by IHG

Holiday Inn Express Chesapeake - Norfolk by IHG

2.5 out of 5
721 Conference Center Drive Chesapeake VA
Fully refundable
The price is AU$174 per night from 19 Apr to 20 Apr
AU$174
19 Apr - 20 Apr
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Everything was great as usual. Definitely my go to place to stay when Im in town. The staff aim to please. Amenities are always available when nedded. Parking was easy and breakfast was delicious..

Reviewed on 30 Mar 2026

Holiday Inn Express Chesapeake - Norfolk by IHG
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.

What to do in Chesapeake

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.