Title: Windsor Vacation Packages & Trips 2026 from CA $1,102 | 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. ![Sea Ranch Resort](https://images.trvl-media.com/lodging/2000000/1340000/1336400/1336351/796917e8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sea Ranch Resort CA $1,102 per person May 15 - May 18 found 19 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Norfolk (ORF) 8.6/10 Excellent! (1,000 reviews) Very spartan room which was fine as it had decent amenties. One small thing that would really help would be to fix the drapery on the window. It was hanging off the rod & made the room look terrible. Staff was friendly & efficient. Reviewed on Mar 28, 2026 ![Ocean 27](https://images.trvl-media.com/lodging/1000000/20000/14100/14028/c2441dc5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ocean 27 Northeast Virginia Beach CA $2,811 per person Jun 4 - Jun 8 found 1 day ago Roundtrip flight included St. John's (YYT) to Norfolk (ORF) 6.4/10 (1,059 reviews) Close to beach. Ground level beach access rooms. Grounds need to be picked-up a bit. Centrally located along boardwalk. Reviewed on Oct 13, 2025 ![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 $1,532 per person Jun 4 - Jun 8 found 1 day ago Roundtrip flight included St. John's (YYT) to Norfolk (ORF) 8/10 Very Good! (1,347 reviews) The rooms was very clean , a little outdated but we still slept pretty comfortably. It’s not a bad stay for the price. Reviewed on Apr 4, 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 $1,495 per person Jun 4 - Jun 8 found 1 day ago Roundtrip flight included St. John's (YYT) to Norfolk (ORF) 8.4/10 Very Good! (1,215 reviews) This was a nice property on the beach. Perfect to see the sunrise each morning. Reviewed on Apr 1, 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 $1,408 per person Jun 4 - Jun 8 found 1 day ago Roundtrip flight included St. John's (YYT) to Norfolk (ORF) 7.8/10 Good! (1,471 reviews) Great place to stay! Room and amenities were far beyond my expectation. This was my first day with my family and we will definitely do it again this year. Reviewed on Mar 30, 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 $148 CA $172 total Apr 9 - Apr 10 includes taxes & fees 8.6/10 Excellent! (1,331 reviews) Managers special apps, cheese squares & chips? Room was great! Looked forward to breakfast. Place was over rum by Bus Tours, several buses. Single breakfast chef taking omelet and egg orders was buried and other breakfast items were running low to out! If packed management to staff more appropriately. ... Reviewed on Apr 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=09%2F04%2F2026&endDate=10%2F04%2F2026&selected=1172219&PinnedHotelID=1172219&HadPinnedHotel=true®ionId=3000460770) ![Comfort Inn & Suites Hampton near Coliseum](https://images.trvl-media.com/lodging/2000000/1550000/1545200/1545185/8b180fc8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites Hampton near Coliseum 1551 Hardy Cash Dr Hampton VA Fully refundable CA $128 CA $150 total Apr 20 - Apr 21 includes taxes & fees 8.8/10 Excellent! (1,200 reviews) When I arrived I was told they were short staffed and no rooms were available. I let the check-in person know I had an event to attend. She went and found me a room. Reviewed on Mar 30, 2026 [](https://expedia.ca/Hotel-Search?startDate=20%2F04%2F2026&endDate=21%2F04%2F2026&selected=1545185&PinnedHotelID=1545185&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 $208 CA $243 total Apr 6 - Apr 7 includes taxes & fees 8.2/10 Very Good! (1,003 reviews) Good experience Reviewed on Apr 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=06%2F04%2F2026&endDate=07%2F04%2F2026&selected=11622&PinnedHotelID=11622&HadPinnedHotel=true®ionId=3000460770) [See all 725 properties in Windsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=05%2F04%2F2026&endDate=06%2F04%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