Title: Windsor Vacation Packages & Trips 2026 from CA $551 | Expedia.ca [Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d7880.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d7880.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.ca/Cheap-Flights-To-Windsor.d7880.Travel-Guide-Flights)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d7880.Car-Rental-Guide) ![](https://images.trvl-media.com/place/7880/7cec51be-160c-4c0b-93cb-c61bca24b629.jpg?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 #### Your Windsor Vacation The cosmopolitan vibe and rich history are just the beginning of the things Windsor has going for it. Enjoy the best parts of this fascinating city your way with a personalized Windsor vacation package. A trip to Windsor is an ideal opportunity to see the sights. Be sure to stop by big-name attractions such as [XL Center](https://www.expedia.ca/XL-Center-Downtown-Hartford.d501167.Vacation-Attraction), [Xfinity Theatre](https://www.expedia.ca/Xfinity-Theatre-North-Meadows.d6237450.Vacation-Attraction) and [University of Hartford](https://www.expedia.ca/University-Of-Hartford-Hartford.d501174.Vacation-Attraction). Whatever your travel plans or budget, putting together the ultimate tailored Windsor vacation is simple with Expedia. ## Top Windsor Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Quality Suites Stratford](https://images.trvl-media.com/lodging/2000000/1770000/1764400/1764336/ded227e6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Quality Suites Stratford CA $551 per person Apr 24 - Apr 26 found 1 day ago Roundtrip flight included Montreal (YUL) to New Haven (HVN) 8/10 Very Good! (1,000 reviews) In the middle of a neighborhood so no close restaurants or amenities Reviewed on Mar 16, 2026 ## Ready to book your vacation to Windsor? Choose your dates ## Windsor Hotel Deals ![HYATT house Hartford North/Windsor](https://images.trvl-media.com/lodging/3000000/2230000/2220600/2220580/98051490_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### HYATT house Hartford North/Windsor 200 Corporate Dr Windsor CT Fully refundableReserve now, pay when you stay CA $165 CA $189 total Apr 3 - Apr 4 includes taxes & fees 9/10 Wonderful! (1,007 reviews) Great hotel but keep the safety bolt locked at all times Reviewed on Mar 22, 2026 [](https://expedia.ca/Hotel-Search?startDate=03%2F04%2F2026&endDate=04%2F04%2F2026&selected=2220580&PinnedHotelID=2220580&HadPinnedHotel=true®ionId=7880) ![Hilton Garden Inn Hartford North/Bradley Int'l Airport](https://images.trvl-media.com/lodging/1000000/540000/531100/531022/1958438c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Garden Inn Hartford North/Bradley Int'l Airport 555 Corporate Dr Windsor CT Fully refundableReserve now, pay when you stay CA $168 CA $193 total Apr 3 - Apr 4 includes taxes & fees 8.8/10 Excellent! (1,001 reviews) One night stay...staff was very courteous, room and lobby nice and clean, and the extended parking ans shuttle service/drivers were prompt and pleasant. Will stay again. Reviewed on Mar 19, 2026 [](https://expedia.ca/Hotel-Search?startDate=03%2F04%2F2026&endDate=04%2F04%2F2026&selected=531022&PinnedHotelID=531022&HadPinnedHotel=true®ionId=7880) ![Marriott Hartford/Windsor Airport](https://images.trvl-media.com/lodging/1000000/810000/806000/805952/17e85132_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Marriott Hartford/Windsor Airport 28 Day Hill Rd Windsor CT Fully refundableReserve now, pay when you stay CA $191 CA $219 total Apr 3 - Apr 4 includes taxes & fees 8.4/10 Very Good! (1,003 reviews) Not close to shopping without a car. Reviewed on Mar 22, 2026 [](https://expedia.ca/Hotel-Search?startDate=03%2F04%2F2026&endDate=04%2F04%2F2026&selected=805952&PinnedHotelID=805952&HadPinnedHotel=true®ionId=7880) [See all 763 properties in Windsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F03%2F2026&endDate=26%2F03%2F2026®ionId=7880) 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) ### Discover the most popular places to visit in Windsor #### Windsor Historical Society You can spend an afternoon browsing the exhibits at Windsor Historical Society during your trip to Windsor. Experience the great live music or attend a sporting event in this family-friendly area. [](https://expedia.ca/Windsor-Historical-Society-Windsor.d553248621555471516.Vacation-Attraction) ## 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