Title: Greenbrier Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,002 Expedia.ca [Greenbrier Travel Guide](https://expedia.ca/Chesapeake-Greenbrier.dx946137804512284672)[Hotels in Greenbrier](https://expedia.ca/Greenbrier-Hotels.d946137804512284672.Travel-Guide-Hotels)[Flights to Chesapeake](https://expedia.ca/Cheap-Flights-To-Chesapeake.d6612.Travel-Guide-Flights)[Greenbrier Car Rentals](https://expedia.ca/Car-Rentals-In-Greenbrier.d946137804512284672.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6612/a9713a83-9e8c-48e1-a2a0-408a1c201fa4.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Greenbrier 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 ## Top Holiday Package Deals in Greenbrier Price found within the past 48 hours. Click for updated prices. ![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 CA $1,002 per person Mar 30 - Apr 5 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to Norfolk (ORF) 8.6/10 Excellent! (329 reviews) Room was cozy and clean. Staff was excellent... Reviewed on Jan 13, 2026 ![Budget Inn Norfolk Va](https://images.trvl-media.com/lodging/1000000/20000/17600/17512/b82e43d8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Budget Inn Norfolk Va Willoughby Spit CA $1,722 per person Mar 30 - Apr 5 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to Norfolk (ORF) 5.8/10 (369 reviews) Management guarantees safety thats most important. There are plenty of restaurants around to choose from. The beach view is beautiful, and the walk to the beach is not gar at all. I enjoy being here. Im from a different state. Reviewed on Jan 5, 2026 ![Holiday Inn & Suites Virginia Beach North Beach by IHG](https://images.trvl-media.com/lodging/1000000/20000/16300/16268/631516bd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn & Suites Virginia Beach North Beach by IHG Northeast Virginia Beach CA $1,151 per person Mar 30 - Apr 5 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to Norfolk (ORF) 7.8/10 Good! (1,242 reviews) Yep great view grear times, Reviewed on Jan 9, 2026 ![Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/12800/12727/8e60d2f4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel Northeast Virginia Beach CA $1,021 per person Mar 30 - Apr 5 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to Norfolk (ORF) 8.4/10 Very Good! (1,197 reviews) I had a great stay and truly enjoyed everything. The property was clean, safe, and quiet, and the location was very convenient. Easy parking, walkable areas, and nearby shopping made it even better. I would definitely stay here again and recommend it to others. Reviewed on Jan 8, 2026 ![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 $2,060 per person Apr 1 - Apr 7 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to Norfolk (ORF) No reviews ## Where to stay in Greenbrier Find the best Greenbrier areas and neighborhoods for the activities you enjoy most. [Learn more about Greenbrier](https://expedia.ca/Chesapeake-Greenbrier.dx946137804512284672) ![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 If you're spending some time in Greenbrier West, Chesapeake Arboretum and Battlefield Historic Park 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 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://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 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) ![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) ### Great Bridge 2 out of top 10 points of interest in this area If you're spending some time in Great Bridge, Chesapeake City Hall and Chesapeake Golf Club are top sights worth seeing. [Find hotel + flight trips in Great Bridge](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Great%20Bridge&DestID=553248635976473375&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Greenbrier 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 $101 CA $118 total Jan 19 - Jan 20 includes taxes & fees 8.6/10 Excellent! (1,000 reviews) Everything is excellent Reviewed on Jan 9, 2026 [](https://expedia.ca/Hotel-Search?startDate=19%2F01%2F2026&endDate=20%2F01%2F2026&selected=6570&PinnedHotelID=6570&HadPinnedHotel=true®ionId=946137804512284672) ![Aloft Chesapeake](https://images.trvl-media.com/lodging/3000000/2180000/2178600/2178508/40b8c7ba_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Aloft Chesapeake 1454 Crossways Boulevard Chesapeake VA Fully refundableReserve now, pay when you stay CA $127 CA $148 total Feb 1 - Feb 2 includes taxes & fees 8.4/10 Very Good! (1,002 reviews) The staff was amazing! Reviewed on Jan 12, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&selected=2178508&PinnedHotelID=2178508&HadPinnedHotel=true®ionId=946137804512284672) ![WoodSpring Suites Chesapeake - Norfolk South](https://images.trvl-media.com/lodging/4000000/3080000/3071800/3071703/24f7fba4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### WoodSpring Suites Chesapeake - Norfolk South 137 Kempsville Rd Chesapeake VA Fully refundableReserve now, pay when you stay CA $96 CA $113 total Jan 19 - Jan 20 includes taxes & fees 5.8/10 (656 reviews) Staff was really welcoming and nice.. I plan on returning. Reviewed on Dec 8, 2025 [](https://expedia.ca/Hotel-Search?startDate=19%2F01%2F2026&endDate=20%2F01%2F2026&selected=3071703&PinnedHotelID=3071703&HadPinnedHotel=true®ionId=946137804512284672) [See all 2,974 properties in Greenbrier](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=946137804512284672) 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) ### Things to do ![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 $190 per adult **76%** of travellers recommend [](https://expedia.ca/things-to-do/city-cruises-norfolk-signature-dinner-cruise.a174659.activity-details) ![Visit Norfolk's Perk Up Pass](https://mediaim.expedia.com/localexpert/47153116/cebb6dd9-72f3-417c-88da-f9e725038575.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Visit Norfolk's Perk Up Pass CA $23 per adult [](https://expedia.ca/things-to-do/visit-norfolks-perk-up-pass.a47153116.activity-details) [See all activities in Chesapeake](https://expedia.ca/things-to-do/search?rid=946137804512284672) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.