Title: Chesapeake City County Vacations & Trips 2026 from CA $1,403 | Expedia.ca [Chesapeake City County Hotels](https://expedia.ca/Destinations-In-Chesapeake-City-County.d553248635976432419.Hotel-Destinations)[Vacation Rentals in Chesapeake City County](https://expedia.ca/Destinations-In-Chesapeake-City-County.d553248635976432419.Vacation-Rental-Destinations)[Chesapeake City County Car Rentals](https://expedia.ca/Destinations-In-Chesapeake-City-County.d553248635976432419.Car-Rental-Destinations) ![](https://images.trvl-media.com/place/6273847/920d6124-d998-482b-9bd7-35767b65c694.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chesapeake City County 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 City County Vacation Leave the planning to us with a Chesapeake City County vacation package. With everything organized before you leave home, the only thing left for you to do is relax and experience this destination's beauty and culture. Not sure where your first stop should be? [Chesapeake](https://www.expedia.ca/Chesapeake.d6612.Destination-Travel-Guides) is among the most popular cities to visit during a trip to Chesapeake City County. Expedia has hotels, flights and all your other travel needs to help you put together your very own customized Chesapeake City County vacation today. ## Top Chesapeake City County Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia](https://images.trvl-media.com/lodging/2000000/1160000/1154700/1154697/8389c2fe_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia Northeast Virginia Beach CA $1,403 per person Apr 2 - Apr 9 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Norfolk (ORF) 8.2/10 Very Good! (1,168 reviews) We had a great stay. The staff was very helpful. The room was amazing and clean. We will be back Reviewed on Jan 31, 2026 ![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 $2,358 per person Apr 10 - Apr 18 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Norfolk (ORF) 9/10 Wonderful! (1,000 reviews) Compared to my first visit, this stay came with a few challenges. The shower wasn’t properly cleaned, and I had to call maintenance for both the showerhead and the safe. The headboard also appeared to be torn, and the restaurants closed at midnight, which was disappointing since nightlife was the main reason I chose The Main. I would consider staying again, but the accommodations were not top-notch. Reviewed on Jan 11, 2026 ![The Ocean Key Virginia Beach Resort](https://images.trvl-media.com/lodging/1000000/530000/529400/529337/25abf259_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ocean Key Virginia Beach Resort Northeast Virginia Beach CA $1,429 per person Apr 2 - Apr 9 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Norfolk (ORF) 7.8/10 Good! (1,448 reviews) I did not enjoy pool like we wanted it was closed for 2 days out of the stay we was there so kids did t get to use it until a day for we was leaving Reviewed on Nov 17, 2025 ![The Atrium Resort, Virginia Beach by Vacatia](https://images.trvl-media.com/lodging/2000000/1150000/1141900/1141831/b72945f5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Atrium Resort, Virginia Beach by Vacatia Northeast Virginia Beach CA $1,514 per person Apr 2 - Apr 9 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Norfolk (ORF) 8.2/10 Very Good! (1,478 reviews) We love the homey feeling of the room. The whole apartment aka hotel room was the best. Can't wait to cone back during the warmer season. Thanks for making my birthday Reviewed on Oct 12, 2025 ![Spacious 4BR Home w/ Pool Family Friendly](https://images.trvl-media.com/lodging/121000000/120520000/120512800/120512753/47e0cdcf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Spacious 4BR Home w/ Pool Family Friendly Central Newport News CA $2,684 per person Apr 10 - Apr 18 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Norfolk (ORF) No reviews ## Chesapeake City County Hotel Deals ![Wingate by Wyndham Chesapeake](https://images.trvl-media.com/lodging/2000000/1520000/1513300/1513238/d607b035_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 $103 CA $121 total Feb 22 - Feb 23 includes taxes & fees 7.8/10 Good! (1,007 reviews) Great customer service Reviewed on Feb 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=1513238&PinnedHotelID=1513238&HadPinnedHotel=true®ionId=553248635976432419) ![Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)](https://images.trvl-media.com/lodging/1000000/10000/5400/5363/c80e2694_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Country Inn & Suites by Radisson, Virginia Beach (Oceanfront) 1801 Atlantic Ave Virginia Beach VA Fully refundable CA $129 CA $151 total Feb 16 - Feb 17 includes taxes & fees 8.2/10 Very Good! (2,495 reviews) Great room! Clean and tidy. Amazing ocean view. Breakfast was great, offered eggs, bacon, muffins, waffles, bagels, cereals, and much more. Definitely stay here again! Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F02%2F2026&endDate=17%2F02%2F2026&selected=5363&PinnedHotelID=5363&HadPinnedHotel=true®ionId=553248635976432419) ![Holiday Inn Va Beach-Oceanside (21st St) by IHG](https://images.trvl-media.com/lodging/1000000/10000/4900/4857/9b6817bb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Va Beach-Oceanside (21st St) by IHG 2101 Atlantic Avenue Virginia Beach VA Fully refundable CA $178 CA $207 total Mar 9 - Mar 10 includes taxes & fees 8.8/10 Excellent! (1,003 reviews) Nice view of the beach Reviewed on Jan 19, 2026 [](https://expedia.ca/Hotel-Search?startDate=09%2F03%2F2026&endDate=10%2F03%2F2026&selected=4857&PinnedHotelID=4857&HadPinnedHotel=true®ionId=553248635976432419) [See all 3,424 properties in Chesapeake City County](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026®ionId=553248635976432419) 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) ## Frequently asked questions ### How much does a Chesapeake City County vacation package cost? ### How do I get a cheap travel package to Chesapeake City County? ### What are the top hotels in Chesapeake City County? ### How far in advance should I book my Chesapeake City County vacation? ### What does an Expedia Chesapeake City County travel package include? ### What should I know before booking a Chesapeake City County travel package? ### Can I choose my airline with a Chesapeake City County Expedia vacation package? ### If I'm not able to travel, can I cancel my Chesapeake City County vacation package? \* 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