Chesapeake Vacation Packages
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Your Chesapeake Vacation
Lock in a Chesapeake vacation package and concentrate on what matters — enjoying yourself. No more planning headaches, just a lot more free time to uncover what's special about this lively city, such as its rich history and family-friendly attractions. Make your trip to Chesapeake even more fun by including some sightseeing. Greenbrier Mall, Oak Grove Lake Park and Chesapeake City Park are among the popular attractions you'll want to explore. Your perfect Chesapeake vacation is just clicks away. Search flights, hotels and more on Expedia for a trip that's tailored just for you.
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.
Deep Creek South
1 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.
Greenbrier East
If you're looking for some top things to see and do in Greenbrier East and surrounding area, you can visit Greenbrier Mall and Chesapeake Conference Center.
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.
Ready to book your vacation to Chesapeake?
Chesapeake Hotel Deals
Comfort Suites Chesapeake - Norfolk
1550 Crossways Blvd Chesapeake VA
Fully refundable
CA $129
CA $151 total
Oct 18 - Oct 19
includes taxes & fees
8.8/10 Excellent! (1,097 reviews)
"Exceptionally clean"
Reviewed on Sep 17, 2026
Hyatt Studios Chesapeake
101 Volvo Parkway Chesapeake VA
Fully refundableReserve now, pay when you stay
CA $200
CA $233 total
Sep 29 - Sep 30
includes taxes & fees
YourSpace Hotels Chesapeake
2137 Starmount Parkway Chesapeake VA
Fully refundableReserve now, pay when you stay
CA $137
CA $161 total
Oct 18 - Oct 19
includes taxes & fees
9.4/10 Exceptional! (209 reviews)
"had never been there before. The room had alot to utilize if you were in it more than I was. Pretty much full kitchen, laundry facilities in bathroom. Room was quite good sized. Only thing it could have used was a small coffee maker in room. They did have coffee in lobby at all times which is great, ..."
Reviewed on Sep 16, 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)
You can browse for the perfect souvenirs at Greenbrier Mall during your visit to Chesapeake. Stroll along the beautiful beaches or attend a sporting event in the area.
Chesapeake Square Mall
8.2/10 (429 reviews)
You can find the perfect gifts to bring home at Chesapeake Square Mall during your trip to Chesapeake. Discover the top-notch restaurants and acclaimed theater scene in this family-friendly area.
Chesapeake Conference Center
7.8/10 (169 reviews)
After visiting Chesapeake Conference Center, make a plan to see the other sights and activities in Chesapeake. Experience the area's great live music and acclaimed theater scene.
Chesapeake City Park
8.2/10 (180 reviews)
Chesapeake City Park is just one of the places to see in Chesapeake, so why not enjoy the other things to explore during your travels? Stroll along the area's beautiful beaches or experience its acclaimed theater scene.
Photo by Kaylee Spinhirn
Oak Grove Lake Park
7.6/10 (39 reviews)
After visiting Oak Grove Lake Park, make a plan to see the other sights and activities in Chesapeake. Experience the area's acclaimed theater scene or attend a sporting event.
Lake Drummond
7.8/10 (12 reviews)
Commune with nature and explore the great outdoors at Lake Drummond during your travels in Chesapeake. Stroll along the beautiful beaches in this romantic area, or check out its top-notch restaurants.
Dismal Swamp Canal
Dismal Swamp Canal is just one of the places to see in Chesapeake, so why not enjoy the other things to explore during your travels? While in this family-friendly area, you can enjoy the coffeehouses.
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.
What to do in Chesapeake
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
CA $59
per adult
80% of travellers recommend
City Cruises Norfolk: Signature Dinner Cruise
CA $115
per adult
76% of travellers recommend
City Cruises Norfolk: Signature Brunch Cruise
CA $109
per adult
88% of travellers recommend
Frequently asked questions
How much does a Chesapeake vacation package cost?
You can snap up a vacation package to this destination from CA $688 on Expedia. However, how much your vacation to Chesapeake costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Chesapeake?
You can generally find reduced prices and better availability in January, February and November. Explore our cheap Chesapeake vacation packages and you could get some great off-season deals.
How many days is enough for Chesapeake?
With about 2 days, you'll have plenty of time to visit popular neighbourhoods such as Greenbrier East and Greenbrier West during your Chesapeake vacation. Be sure to also add Chesapeake Central Library and Portlock Galleries at SoNo to your sightseeing list. In the mood for more adventures? Consider venturing outside of Chesapeake on day trips and tours.
Is it worth booking a vacation package to Chesapeake?
Well known for its nature, adventure sports and hiking, a Chesapeake vacation is a hit with all kinds of visitors. Be sure to check out major sights like Portlock Galleries at SoNo and Oak Grove Lake Park, and consider renting some wheels for day trips to discover even more.
How to find the best Chesapeake package deals?
Start your search for a Chesapeake package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Chesapeake package deal right away, just play around with your dates and search again. Remember 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 Chesapeake escape by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to view some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Chesapeake?
If you have your Chesapeake vacation dates finalized, book as soon as you can to score some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Chesapeake?
- Choose the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Chesapeake.
- Plan your budget wisely: In addition to the cost of your stay, you'll need to factor in other expenses. These include flights, transportation and food. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Chesapeake.
- Decide your trip length: Consider how much time you'd like to spend discovering Chesapeake. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
- Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to find 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.
