Chesapeake Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
If you're spending some time in Greenbrier, Greenbrier Mall and Chesapeake Arboretum are top sights worth seeing.
Greenbrier East
While visiting Greenbrier East, you might make a stop by sights like Greenbrier Mall and Jillian's Billiards.
Greenbrier West
If you're spending some time in Greenbrier West, Chesapeake Arboretum and Bowlero Chesapeake are top sights worth seeing.
South Norfolk
South Norfolk might not have many top sights, but Chesapeake Conference Center and Greenbrier Mall are two attractions nearby that you can check out.
Deep Creek South
2 out of top 10 points of interest in this area
Suburban community with a rural touch, Deep Creek is connected to the historic Dismal Swamp Canal, a National Historic Civil Engineering Landmark. Located along the original U.S. Highway 17 route, it offers easy access to nearby attractions.
Find the Best Chesapeake Vacation Packages
Chesapeake Hotel Deals
Wyndham Virginia Beach Oceanfront
5700 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
₩112,234
₩142,418 total
Sep 2 - Sep 3
includes taxes & fees
7.8/10 Good! (1,968 reviews)
"Could use a bigger outdoor pool and could be cleaner but it is in a nice quiet area and the beach is not crowded and quiet."
Reviewed on Aug 13, 2026
Ocean Resort
Atlantic Avenue,2417 Virginia Beach VA
Fully refundableReserve now, pay when you stay
₩122,156
₩162,922 total
Sep 14 - Sep 15
includes taxes & fees
7.8/10 Good! (1,676 reviews)
"Excellent place for families and kids.."
Reviewed on Aug 13, 2026
Crowne Plaza Virginia Beach Town Center by IHG
4453 Bonney Rd Virginia Beach VA
Fully refundable
₩131,790
₩154,393 total
Sep 7 - Sep 8
includes taxes & fees
8.4/10 Very Good! (488 reviews)
"Room 211 was riddled with issues. I only stayed 1 night fortunately. The shower door was on a track and wouldn't stay closed so I had to place a bottle of bodywash to keep it shut. By morning I figured out the coffee marker couldn't be plugged in so I moved it to the desk. Finally, the bathroom faucet ..."
Reviewed on Aug 13, 2026
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 center features over 100 stores and eateries, plus a Cinema Café for dining during movies. 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 theater. Visit weekday mornings for a relaxed experience at this regional retail center undergoing a $30 million revitalization.
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 customized 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.
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.
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.
Frequently asked questions
How much does a Chesapeake vacation 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 vacation to Chesapeake costs.
What are the cheapest months to go to Chesapeake?
If you'd like to book a cheap Chesapeake vacation package, consider planning a trip in January, February and November. You'll generally find better prices on accommodations and flights during these months — perfect for travelers wishing to save money.
How many days is enough for Chesapeake?
Chesapeake vacations 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 neighborhoods 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 vacation package to Chesapeake?
Well known for its nature, adventure sports and hiking, a Chesapeake vacation 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 vacation as a package?
You can enjoy significant savings on your next Chesapeake retreat by booking a customized vacation 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 vacation 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, favorite 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 vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
