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.
Top Chesapeake Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Delta Hotels by Marriott Virginia Beach Waterfront Suites
Northeast Virginia Beach
CA $1,264
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
8.4/10 Very good! (1,500 reviews)
Hotel was very clean and close to what we were looking to do.
Reviewed on Aug 8, 2026
The Atrium Resort, Virginia Beach by Vacatia
Northeast Virginia Beach
CA $932
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
8.2/10 Very good! (1,593 reviews)
I stayed with my husband and two children. The room was spacious and had everything we needed for the stay. Some cosmetic needs to be done such as broken bathroom tiles, shower loose items, and some stains on the towels. Room temperature was good and the bed and sofa bed were comfortable.
Reviewed on Aug 7, 2026
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
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.
Ready to book your vacation to Chesapeake?
Chesapeake Hotel Deals
Hyatt Studios Chesapeake
101 Volvo Parkway Chesapeake VA
Fully refundableReserve now, pay when you stay
CA $177
CA $206 total
Aug 16 - Aug 17
includes taxes & fees
8.4/10 Very good! (75 reviews)
"This is a brand new hotel and it is very nice. Comfy bed and linens. Quiet."
Reviewed on Aug 9, 2026
Wyndham Virginia Beach Oceanfront
5700 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
CA $119
CA $150 total
Aug 31 - Sep 1
includes taxes & fees
7.8/10 Good! (1,937 reviews)
"Everything was great!"
Reviewed on Aug 8, 2026
Ocean Resort
Atlantic Avenue,2417 Virginia Beach VA
Fully refundableReserve now, pay when you stay
CA $130
CA $171 total
Sep 7 - Sep 8
includes taxes & fees
7.8/10 Good! (1,680 reviews)
"The location was wonderful as well as the staff. The parking was horrible!!! People did smoke on the balconies and since there is no wall between them it comes on over to the next balcony big time !! Something was leaking above my balcony and splattering on me when I sat out there."
Reviewed on Aug 9, 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 great live music 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 family-friendly 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 Golf Club
7.4/10 (93 reviews)
Enjoy a round of golf in Chesapeake at Chesapeake Golf Club. Experience the great live music or attend a sporting event in this family-friendly area.
What to do in Chesapeake
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
CA $60
per adult
100% of travellers recommend
City Cruises Norfolk: Signature Dinner Cruise
CA $158
per adult
76% of travellers recommend
City Cruises Norfolk: Signature Brunch Cruise
CA $136
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 $834 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.
