Title: Chesapeake Vacation Packages & Trips 2025/2026 from CA $968 | 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/6612/a9713a83-9e8c-48e1-a2a0-408a1c201fa4.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chesapeake Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Kaylee Spinhirn - ## 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. ## Top Chesapeake Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Delta Hotels by Marriott Virginia Beach Waterfront Suites](https://images.trvl-media.com/lodging/41000000/40900000/40896500/40896449/6e910a6c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Delta Hotels by Marriott Virginia Beach Waterfront Suites Northeast Virginia Beach CA $968 per person Jan 10 - Jan 17 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Norfolk (ORF) 8.4/10 Very Good! (1,414 reviews) Need more light in bathroom vanity and around full length mirror. Too dark. Reviewed on Oct 24, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-10/2026-01-17/?FromAirport=YYC&Destination=ORF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=40896449&paandie=true&dealMarker=ltb-f-s0gICvrDpdHLMxeM1_OA7TUeBrAk6L68GSe1kR-2OCaBiIhsk2q3-E54w1) ![TRU by Hilton Chesapeake, VA](https://images.trvl-media.com/lodging/93000000/92930000/92925200/92925103/1ca0dd05_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### TRU by Hilton Chesapeake, VA Greenbrier East CA $1,019 per person Jan 10 - Jan 17 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Norfolk (ORF) 8.6/10 Excellent! (298 reviews) Everything about our stay at the Tru by Hilton was great, except the maintenence on the hot water. We arrived on Wednesday night, took one shower and couldnt get another shower until friday afternoon. Reviewed on Oct 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-10/2026-01-17/?FromAirport=YYC&Destination=ORF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=92925103&paandie=true&dealMarker=VCE7QcuKn8xLCDGDCnmXgA6mh8XCA9q_9FUElDbkNLcQuG27sz5tLhjAU-ULTG6H) ![Hampton Inn & Suites Newport News (Oyster Point)](https://images.trvl-media.com/lodging/1000000/30000/21100/21074/1e9dfcd1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn & Suites Newport News (Oyster Point) Central Newport News CA $1,348 per person Dec 26 - Jan 2 found 15 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Norfolk (ORF) 8.8/10 Excellent! (560 reviews) Shida checked us in and out. She was very friendly and helpful. She also accommodated our request for early check in with our cats. She’s the best! Reviewed on Oct 24, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2026-01-02/?FromAirport=YEG&Destination=ORF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21074&paandie=true&dealMarker=VCE7QcuKn8xLCDGDCnmXgMmNuumeMZ2pSpZHSlPzFhxYHXMUbt1wSHkatZJSSZBU) ![Courtyard by Marriott Chesapeake](https://images.trvl-media.com/lodging/1000000/50000/43100/43064/f2e59564_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Courtyard by Marriott Chesapeake Greenbrier East CA $991 per person Jan 10 - Jan 17 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Norfolk (ORF) 7.4/10 Good! (581 reviews) Under hotel Property undergoing remodeling. Some areas and rooms have been updated but some have not +Elevator, -yoilets not "bolted" to floor -Common areas and courtyard closed -pool? -Limited parking w/ access to building entrance way Reviewed on Oct 24, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-10/2026-01-17/?FromAirport=YYC&Destination=ORF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=43064&paandie=true&dealMarker=VCE7QcuKn8xLCDGDCnmXgGxwHiCAtWICL7bQSgNDMquQq1aJcIIi2bSDbbTxIfIO) ![Hilton Norfolk The Main](https://images.trvl-media.com/lodging/17000000/16420000/16417400/16417334/ec9c304d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Norfolk The Main Downtown Norfolk CA $1,553 per person Jan 10 - Jan 17 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Norfolk (ORF) 9/10 Wonderful! (1,004 reviews) Our ship out of the cruise port that is right next store was delayed they allowed us late check out and stored our luggage so we could walk around until we could board pur ship. Also for those cruising it is a quick walk to the cruise port no driving needed Reviewed on Oct 18, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-10/2026-01-17/?FromAirport=YYC&Destination=ORF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=16417334&paandie=true&dealMarker=KHWPRtfpgQLCPs1aqh3ZsQHJNCVwR0utYVjr48DA5SAtqKFCLV4Mfug_rvngXFNb) ## 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) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Greenbrier West 2 out of top 10 points of interest in this area 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) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/481000/481331-Greenbrier-Mall.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) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/481000/481331-Greenbrier-Mall.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Greenbrier 1 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) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.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) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/481000/481121-Chesapeake-Square-Mall.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 ![Comfort Suites Chesapeake - Norfolk](https://images.trvl-media.com/lodging/1000000/10000/6600/6570/74e17a93_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 $118 CA $138 total Nov 2 - Nov 3 includes taxes & fees 8.4/10 Very Good! (1,030 reviews) Good condition and excellent communication with the front desk Reviewed on Oct 19, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=6570&PinnedHotelID=6570&HadPinnedHotel=true®ionId=6612) ![Red Roof Inn Chesapeake Conference Center](https://images.trvl-media.com/lodging/1000000/10000/2000/1927/a9448b44_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Red Roof Inn Chesapeake Conference Center 724 Woodlake Dr, Chesapeake, VA Fully refundableReserve now, pay when you stay CA $99 CA $117 total Nov 16 - Nov 17 includes taxes & fees 6.8/10 (1,001 reviews) Clean rooms Reviewed on Oct 10, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=1927&PinnedHotelID=1927&HadPinnedHotel=true®ionId=6612) ![STUDIOS & SUITES 4 LESS CHESAPEAKE ](https://images.trvl-media.com/lodging/1000000/50000/40500/40428/e945abb1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### STUDIOS & SUITES 4 LESS CHESAPEAKE 2222 S Military Hwy, Chesapeake, VA Fully refundableReserve now, pay when you stay CA $77 CA $92 total Oct 26 - Oct 27 includes taxes & fees 6.6/10 (614 reviews) Nice staff. Reviewed on Oct 23, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=40428&PinnedHotelID=40428&HadPinnedHotel=true®ionId=6612) [See all 3,360 properties in Chesapeake](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F10%2F2025&endDate=27%2F10%2F2025®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 ![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 $57 per adult **80%** of travellers recommend [](https://expedia.ca/things-to-do/norfolks-combo-tickets-virginia-zoo-battleship-wisconsin.a1186873.activity-details) ![Deck area aboard the Spirit of Norfolk Dinner Cruise in Virginia ](https://mediaim.expedia.com/localexpert/174659/e709d57f-50ab-4b75-a124-6d7c3466f431.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Spirit of Norfolk Signature Dinner Cruise CA $208 per adult **72%** of travellers recommend [](https://expedia.ca/things-to-do/spirit-of-norfolk-signature-dinner-cruise.a174659.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) #### Spirit of Norfolk Signature Brunch Cruise CA $159 per adult **88%** of travellers recommend [](https://expedia.ca/things-to-do/spirit-of-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 ![QR code to download the app](data:image/png;base64,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)