Title: Chesapeake Vacation Packages & Trips 2026 | Expedia.ca [Chesapeake Travel Guide](https://expedia.ca/Chesapeake.dx6612)[Hotels in Chesapeake](https://expedia.ca/Chesapeake-Hotels.d6612.Travel-Guide-Hotels)[Vacation Rentals in Chesapeake](https://expedia.ca/Chesapeake-Vacation-Rentals.d6612.Travel-Guide-VacationRentals)[Flights to Chesapeake](https://expedia.ca/Cheap-Flights-To-Chesapeake.d6612.Travel-Guide-Flights)[Chesapeake Car Rentals](https://expedia.ca/Car-Rentals-In-Chesapeake.d6612.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6608/0c611f9e-81b9-471c-8c9d-00c1df7fb2ec.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chesapeake Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### 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](https://www.expedia.ca/Greenbrier-Mall-Greenbrier-East.d6273847.Vacation-Attraction), [Oak Grove Lake Park](https://www.expedia.ca/Oak-Grove-Lake-Park-Greenbrier-West.d6301205.Vacation-Attraction) and [Chesapeake City Park](https://www.expedia.ca/Chesapeake-City-Park-Greenbrier-East.d6083011.Vacation-Attraction) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_6612) ## Where to stay in Chesapeake Find the best Chesapeake areas and neighborhoods for the activities you enjoy most. [Learn more about Chesapeake](https://expedia.ca/Chesapeake.dx6612) ![Silhouettes of trees in Great Dismal Swamp. Virginia, United States.](https://images.trvl-media.com/place/553248635976479827/3e7f7160-d17f-4047-85a3-7e12c732b1a8.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Greenbrier East 1 out of top 10 points of interest in this area While visiting Greenbrier East, you might make a stop by sights like Greenbrier Mall and Jillian's Billiards. [Find hotel + flight trips in Greenbrier East](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Greenbrier%20East&DestID=553248635976479827&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![1.5 miles around. No swimming. But a playground for the kiddos, dog friendly and tons of fishing spots :) ](https://images.trvl-media.com/place/6612/a9713a83-9e8c-48e1-a2a0-408a1c201fa4.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Greenbrier 4 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. [Find hotel + flight trips in Greenbrier](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Greenbrier&DestID=946137804512284672&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Newport News, Virginia, USA](https://images.trvl-media.com/place/553248635976388783/200cad18-a893-4842-a3b9-359f8cc97e65.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### 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. [Find hotel + flight trips in South Norfolk](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=South%20Norfolk&DestID=553248635976388783&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Traveling south on the intracostal waterway. great bridge va.](https://images.trvl-media.com/place/6612/7937059d-5412-4b6d-aa49-26aec8b431f3.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Greenbrier West If you're spending some time in Greenbrier West, Bowlero Chesapeake and Rivercrest Play Area are top sights worth seeing. [Find hotel + flight trips in Greenbrier West](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Greenbrier%20West&DestID=553248635976480700&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Aerial panorama of Chesapeake Bay Bridge Tunnel at sunset. CBBT is a 17.6-mile bridge tunnel that crosses the mouth of the Chesapeake Bay.](https://images.trvl-media.com/place/553248635976469582/a00ce0ef-b210-4160-a5db-1e10c2ab70e6.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Western Branch North 1 out of top 10 points of interest in this area 4/5(1 area review) If you're spending some time in Western Branch North, Chesapeake Square Mall and Bowlero Western Branch are top sights worth seeing. [Find hotel + flight trips in Western Branch North](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Western%20Branch%20North&DestID=553248635976469582&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Ready to book your vacation to Chesapeake? Choose your dates ## Chesapeake Hotel Deals ![Wingate by Wyndham Chesapeake](https://images.trvl-media.com/lodging/2000000/1520000/1513300/1513238/0d94729b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wingate by Wyndham Chesapeake 817 Greenbrier Circle Chesapeake VA Fully refundableReserve now, pay when you stay CA $111 CA $130 total Mar 22 - Mar 23 includes taxes & fees 8/10 Very Good! (1,002 reviews) There was urine on the sheet I pulled off and the mattress was covered in urine staining Reviewed on Mar 12, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=1513238&PinnedHotelID=1513238&HadPinnedHotel=true®ionId=6612) ![Comfort Suites Chesapeake - Norfolk](https://images.trvl-media.com/lodging/1000000/10000/6600/6570/038be8fc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Suites Chesapeake - Norfolk 1550 Crossways Blvd Chesapeake VA Fully refundableReserve now, pay when you stay CA $125 CA $147 total Mar 29 - Mar 30 includes taxes & fees 8.8/10 Excellent! (1,000 reviews) Great stay Reviewed on Mar 11, 2026 [](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=6570&PinnedHotelID=6570&HadPinnedHotel=true®ionId=6612) ![TRU by Hilton Chesapeake, VA](https://images.trvl-media.com/lodging/93000000/92930000/92925200/92925103/7e3313a2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### TRU by Hilton Chesapeake, VA 1570 CROSSWAYS BLVD Chesapeake VA Fully refundableReserve now, pay when you stay CA $133 CA $159 total Mar 22 - Mar 23 includes taxes & fees 8.6/10 Excellent! (398 reviews) Great hotel Reviewed on Mar 11, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=92925103&PinnedHotelID=92925103&HadPinnedHotel=true®ionId=6612) [See all 3,389 properties in Chesapeake](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=13%2F03%2F2026&endDate=14%2F03%2F2026®ionId=6612) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### What to do in Chesapeake ![View of the water and the Spirit of Norfolk Dinner Cruise ship](https://mediaim.expedia.com/localexpert/174659/794d9e61-87fc-4a64-b0b9-9b590737e3a7.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### City Cruises Norfolk: Signature Dinner Cruise CA $133 per adult **76%** of travellers recommend [](https://expedia.ca/things-to-do/city-cruises-norfolk-signature-dinner-cruise.a174659.activity-details) ![Virginia Zoo](https://mediaim.expedia.com/localexpert/1186873/7f097ff9-ed91-446b-81f3-777883b6b643.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin CA $58 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/norfolks-combo-tickets-virginia-zoo-battleship-wisconsin.a1186873.activity-details) ![View of Spirit of Norfolk](https://mediaim.expedia.com/localexpert/434982/dcd9584b-e114-4bc2-9c6e-f55b97e7f340.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### City Cruises Norfolk: Signature Brunch Cruise CA $133 per adult **88%** of travellers recommend [](https://expedia.ca/things-to-do/city-cruises-norfolk-signature-brunch-cruise.a434982.activity-details) [See all activities in Chesapeake](https://expedia.ca/things-to-do/search?rid=6612) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app