Title: Windsor Vacation Packages & Trips 2026 from CA $1,158 | Expedia.ca [Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d3000460770.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d3000460770.Travel-Guide-VacationRentals)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d3000460770.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Windsor 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 ## Top Windsor Vacation Deals Price found within the past 48 hours. Click for updated prices. ![TRU by Hilton Chesapeake, VA](https://images.trvl-media.com/lodging/93000000/92930000/92925200/92925103/7e3313a2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### TRU by Hilton Chesapeake, VA Greenbrier East CA $1,158 per person Apr 25 - May 2 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Norfolk (ORF) 8.6/10 Excellent! (396 reviews) Everything was great! The room and bathroom were neat and clean. The bed was comfortable. Breakfast had many options, more than I was expecting. Check in was a breeze. It was very quiet. The location was perfect—very close to the freeway and there were restaurants very close. The only con I have is that the AC in the room sounded like there were crickets in the room when it was running. It made it somewhat difficult to fall asleep. Reviewed on Mar 22, 2026 ![Boardwalk Resort and Villas](https://images.trvl-media.com/lodging/1000000/920000/910400/910351/4f90a79f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boardwalk Resort and Villas Northeast Virginia Beach CA $1,159 per person Apr 25 - May 2 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Norfolk (ORF) 8.6/10 Excellent! (1,018 reviews) Room was clean, staff very friendly Reviewed on Mar 23, 2026 ![The Ocean Key Virginia Beach Resort](https://images.trvl-media.com/lodging/1000000/530000/529400/529337/87f7858a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ocean Key Virginia Beach Resort Northeast Virginia Beach CA $1,269 per person Apr 25 - May 2 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Norfolk (ORF) 7.8/10 Good! (1,471 reviews) The laundry was up to part. The staff was good except for not letting us know about the marathon on check out day and some other things they didn't let us know about. Over all the stay was good Reviewed on Mar 25, 2026 ![Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/12800/12727/26394a34_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel Northeast Virginia Beach CA $1,235 per person Apr 25 - May 2 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Norfolk (ORF) 8.4/10 Very Good! (1,215 reviews) Helpfuly staff and great in site bar and grille Reviewed on Mar 24, 2026 ![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 $1,224 per person Apr 25 - May 2 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Norfolk (ORF) 8.2/10 Very Good! (1,479 reviews) Staff very friendly. Reviewed on Mar 22, 2026 ## Ready to book your vacation to Windsor? Choose your dates ## Windsor Hotel Deals ![Embassy Suites by Hilton Hampton Convention Center](https://images.trvl-media.com/lodging/2000000/1180000/1172300/1172219/f5721060_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Hampton Convention Center 1700 Coliseum Drive Hampton VA Fully refundableReserve now, pay when you stay CA $123 CA $144 total Mar 30 - Mar 31 includes taxes & fees 8.6/10 Excellent! (1,306 reviews) Everyone was very friendly and the property is very well kept. Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=30%2F03%2F2026&endDate=31%2F03%2F2026&selected=1172219&PinnedHotelID=1172219&HadPinnedHotel=true®ionId=3000460770) ![Wyndham Garden Norfolk Downtown](https://images.trvl-media.com/lodging/1000000/10000/500/472/0d975282_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wyndham Garden Norfolk Downtown 700 Monticello Avenue Norfolk VA Fully refundableReserve now, pay when you stay CA $129 CA $152 total Apr 5 - Apr 6 includes taxes & fees 6.8/10 (1,007 reviews) Nice place. Additional $15 for parking though should be told about I didn't realize tell I got credit card bill Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=472&PinnedHotelID=472&HadPinnedHotel=true®ionId=3000460770) ![Sheraton Norfolk Waterside Hotel](https://images.trvl-media.com/lodging/1000000/20000/11700/11622/ed53c7b5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sheraton Norfolk Waterside Hotel 777 Waterside Dr Norfolk VA CA $170 CA $199 total Apr 1 - Apr 2 includes taxes & fees 8.2/10 Very Good! (1,001 reviews) On this app, the room I chose had a balcony but that was not the case. The property was still very nice and service was over and above. Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F04%2F2026&endDate=02%2F04%2F2026&selected=11622&PinnedHotelID=11622&HadPinnedHotel=true®ionId=3000460770) [See all 715 properties in Windsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F03%2F2026&endDate=27%2F03%2F2026®ionId=3000460770) 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) ## 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