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
Greenbrier
5 out of top 10 points of interest in this area
While visiting Greenbrier, you might make a stop by sights like Greenbrier Mall and Chesapeake Arboretum.
Greenbrier East
If you're spending some time in Greenbrier East, Greenbrier Mall and Jillian's Billiards are top sights worth seeing.
Greenbrier West
While visiting Greenbrier West, you might make a stop by sights like Chesapeake Arboretum and Bowlero Chesapeake.
Deep Creek South
1 out of top 10 points of interest in this area
While visiting Deep Creek South, you might make a stop by sights like The Crossings at Deep Creek Shopping Center and Deep Creek Park.
South Norfolk
If you're looking for some top things to see and do in South Norfolk and surrounding area, you can visit Chesapeake Conference Center and Greenbrier Mall.
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
Comfort Suites Chesapeake - Norfolk
1550 Crossways Blvd Chesapeake VA
Fully refundable
AU$149
7 Sept - 8 Sept
includes taxes & fees
8.8/10 Excellent! (1,076 reviews)
"Carpet in the rooms need to be updated. It smelled a little musty."
Reviewed on 23 Aug 2026
Wyndham Virginia Beach Oceanfront
5700 Atlantic Ave Virginia Beach VA
AU$166
7 Sept - 8 Sept
includes taxes & fees
Ocean Resort
Atlantic Avenue,2417 Virginia Beach VA
AU$152
20 Sept - 21 Sept
includes taxes & fees
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.
Stay near popular Chesapeake attractions
Greenbrier Mall
8.4/10 (837 reviews)
This regional shopping centre features over 100 stores and eateries, plus a Cinema Café for dining during films. Families enjoy the supervised soft play area and convenient amenities while shopping.
Chesapeake Square Mall
8.2/10 (429 reviews)
Chesapeake Square Mall blends shopping with entertainment at its 12-screen Cinemark XD theatre. Visit weekday mornings for a relaxed experience at this regional retail centre undergoing a $30 million revitalisation.
Chesapeake Conference Center
7.8/10 (169 reviews)
This versatile 39,000-square-foot venue hosts elegant weddings to professional conferences in Chesapeake, Virginia. The on-site catering team delivers customised dining experiences with free Wi-Fi and parking.
Chesapeake City Park
8.2/10 (180 reviews)
This sprawling 90-acre recreational haven hosts Chesapeake's signature events like the Jubilee and Symphony Under the Stars. Families enjoy the Fun Forest Playground and peaceful walking trails.
Lake Drummond
7.8/10 (12 reviews)
Lake Drummond, one of only two natural freshwater lakes in Virginia, sits at the heart of Great Dismal Swamp. Paddle through tea-colored waters while spotting black bears and rare birds in this serene ecosystem.
Photo by Kaylee Spinhirn
Oak Grove Lake Park
7.6/10 (39 reviews)
Encircling a serene 65-acre lake, this park's 1.5-mile trail offers picturesque views and abundant wildlife. Enjoy fishing from accessible platforms or relax at shaded picnic areas overlooking the water.
Chesapeake Arboretum
7.6/10 (76 reviews)
Enjoy an outing to Chesapeake Arboretum during your stay in Chesapeake. Amble around the area's beautiful beaches or attend a sporting event.
Dismal Swamp Canal
The oldest hand-dug waterway still operating in America, this historic canal connects the Chesapeake Bay to Albemarle Sound. Paddle through its serene waters while spotting wildlife and exploring its history.
What to do in Chesapeake
City Cruises Norfolk: Signature Dinner Cruise
AU$147
per adult
76% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
AU$61
per adult
100% of travellers recommend
City Cruises Norfolk: Signature Brunch Cruise
AU$138
per adult
88% of travellers recommend
Frequently asked questions
How much does a Chesapeake holiday package cost?
You'll find cheap prices on Expedia for your Chesapeake escape. However, factors like the season, choice of hotel and length of stay will determine how much your holiday to Chesapeake costs.
What are the cheapest months to go to Chesapeake?
If you'd like to book a cheap Chesapeake holiday package, consider planning a trip in January, February and November. You'll generally find better prices on accommodation and flights during these months — perfect for travellers wishing to save money.
How many days is enough for Chesapeake?
Chesapeake holidays can be as short or long as you like, but to get a real feel for this destination, we reckon 2 days is about right. With this timeframe, you can fit in top sights like Chesapeake City Park and Oak Grove Lake Park along with lesser-known spots. Don't forget to visit neighbourhoods such as Greenbrier East and Greenbrier West either. If you're smart with your time, you can even take a day trip from Chesapeake too.
Is it worth booking a holiday package to Chesapeake?
Well known for its nature, adventure sports and hiking, a Chesapeake holiday has something for everyone. Be sure to check out major sights like Portlock Galleries at SoNo and Oak Grove Lake Park, and consider renting a car for day trips to experience even more.
How to find the best Chesapeake package deals?
Begin your search for a Chesapeake package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Chesapeake package deal right away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chesapeake adventure off to a flying start.
Is it cheaper to book a Chesapeake holiday as a package?
You can enjoy significant savings on your next Chesapeake retreat by booking a customised holiday package. Click on the "Package" heading, then select your travel dates and destination to view some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Chesapeake?
Land amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Chesapeake break.
How to plan a trip to Chesapeake?
- Choose the right time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to visit Chesapeake.
- Set a budget: Factor in costs such as flights, food and transportation when working out how much to set aside for your trip to Chesapeake. Then, pick a property that fits your budget, whether that's a wallet-friendly stay or a swankier retreat.
- Decide your trip length: Consider how much time you want to spend discovering Chesapeake. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
- Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to pick a Chesapeake holiday package that brings all your bookings together.
Explore a world of travel with Expedia
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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.
