Title: Windsor Vacation Packages & Trips 2026 from CA $836 | Expedia.ca [Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d553248635975855642.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d553248635975855642.Travel-Guide-VacationRentals)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d553248635975855642.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.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 When you book a vacation package to Windsor, you can relax and enjoy your getaway knowing that all your travel arrangements are under control. Discover the many delights of this vibrant city from your base in a neighborhood like Princeton Meadows, which is great for golfing. During your trip to Windsor, carve some time in your schedule for sightseeing. A popular place to begin exploring is [Working Dog Winery](https://www.expedia.ca/Working-Dog-Winery-Hightstown.d553248621532663729.Vacation-Attraction). Whoever you're escaping with and whatever you plan to spend, your dream Windsor vacation is just a few clicks away with Expedia. ## Top Windsor Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Hotel St. James](https://images.trvl-media.com/lodging/2000000/1150000/1144500/1144474/ecd19bcc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel St. James Manhattan CA $836 per person Mar 12 - Mar 16 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to New York (JFK) 8.8/10 Excellent! (6,546 reviews) The best place to stay on a budget if you’re planning to see Broadway shows. I’ve already reserved The St. James for my trip in April. Reviewed on Feb 6, 2026 ![1 Hotel Central Park](https://images.trvl-media.com/lodging/10000000/9220000/9215600/9215515/524d3c3f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Central Park Manhattan CA $2,010 per person Apr 25 - Apr 29 found 18 hours ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9/10 Wonderful! (1,001 reviews) Excellent stay! Friendly staff, comfortable, beautiful rooms & lobby. Reviewed on Feb 2, 2026 ![The Fifth Avenue Hotel](https://images.trvl-media.com/lodging/97000000/96480000/96472700/96472655/d0a5c1e1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Fifth Avenue Hotel Manhattan CA $2,194 per person Apr 25 - Apr 29 found 18 hours ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 9.6/10 Exceptional! (159 reviews) Staff were lovely, helpful and pleasant. Turndown service way too late, though—9:45 might catch some guests sleeping. Reviewed on Jan 3, 2026 ![1 Hotel Brooklyn Bridge](https://images.trvl-media.com/lodging/16000000/15400000/15399700/15399642/7801a5d8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Brooklyn Bridge CA $1,469 per person Apr 25 - Apr 27 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.8/10 Excellent! (1,000 reviews) The entire stay was exceptional! From the point of entry to departure 10/10 Reviewed on Jan 29, 2026 ![The Pierre, A Taj Hotel, New York](https://images.trvl-media.com/lodging/1000000/30000/20300/20213/8b7fc5c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Pierre, A Taj Hotel, New York Manhattan CA $1,883 per person Apr 25 - Apr 29 found 18 hours ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 9.2/10 Wonderful! (1,007 reviews) Staff warm, & welcoming, bar, great breakfast, & restaurant lovely, don’t miss coffee at the bar in the morning & Friday with the Martinis piano singers. Reviewed on Feb 5, 2026 ## Ready to book your vacation to Windsor? Choose your dates ## Windsor Hotel Deals ![DoubleTree by Hilton Princeton](https://images.trvl-media.com/lodging/1000000/10000/9500/9428/4fa61295_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Princeton 4355 US Highway 1 at Ridge Rd. Princeton NJ Fully refundableReserve now, pay when you stay CA $117 CA $134 total Feb 15 - Feb 16 includes taxes & fees 8.4/10 Very Good! (1,014 reviews) clean room Reviewed on Feb 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=9428&PinnedHotelID=9428&HadPinnedHotel=true®ionId=553248635975855642) ![Hyatt Regency New Brunswick](https://images.trvl-media.com/lodging/1000000/20000/12300/12262/089ba453_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency New Brunswick 2 Albany St New Brunswick NJ Fully refundableReserve now, pay when you stay CA $173 CA $199 total Feb 22 - Feb 23 includes taxes & fees 8.6/10 Excellent! (1,000 reviews) my handicapped accessible room had everything I needed -wheelchair easily navigated all spaces, etc. The food /room service was amazing. I ordered breakfast as well as dinner through room service on two occasions. It was yummy and had a beautiful presentation. Also, My sisters and their kids came ... Reviewed on Jan 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=12262&PinnedHotelID=12262&HadPinnedHotel=true®ionId=553248635975855642) ![The Heldrich Hotel](https://images.trvl-media.com/lodging/2000000/1540000/1531600/1531531/dd23b6be_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Heldrich Hotel 10 Livingston Avenue New Brunswick NJ Fully refundableReserve now, pay when you stay CA $171 CA $203 total Feb 12 - Feb 13 includes taxes & fees 8.4/10 Very Good! (1,002 reviews) Everything was perfect Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F02%2F2026&endDate=13%2F02%2F2026&selected=1531531&PinnedHotelID=1531531&HadPinnedHotel=true®ionId=553248635975855642) [See all 390 properties in Windsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026®ionId=553248635975855642) 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