Title: Windsor Vacation Packages & Trips 2026 from CA $786 | 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 57](https://images.trvl-media.com/lodging/2000000/1210000/1208300/1208242/954f5b6b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel 57 Manhattan CA $786 per person Mar 11 - Mar 16 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.2/10 Very Good! (1,287 reviews) the room was cold. Everything else was ok. Nothing spectacular. Good place to stay for a day or two. Reviewed on Feb 6, 2026 ![Loews Regency New York Hotel](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Loews Regency New York Hotel Manhattan CA $1,845 per person Apr 2 - Apr 7 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9/10 Wonderful! (1,002 reviews) Staff were very accomodating and looked after my family well during our stay. Nothing was too difficult for them. Reviewed on Jan 17, 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 1 day 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 1 day 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 ![Arthouse Hotel New York City](https://images.trvl-media.com/lodging/1000000/20000/12200/12117/922bba74_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arthouse Hotel New York City Manhattan CA $1,410 per person Mar 14 - Mar 21 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.8/10 Excellent! (1,678 reviews) Hip boutique hotel with an industrial cozy vibe. Rooms are sumple but have everything you need. The libby bar and cafe are nice. Attached to Serafina restaurant. Great lication overall and parking across the street. Reviewed on Feb 6, 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) ![MHO Hotel Bordentown](https://images.trvl-media.com/lodging/1000000/20000/10100/10095/0ecbbd01_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### MHO Hotel Bordentown 187 US 130 and 206 Bordentown NJ Fully refundableReserve now, pay when you stay CA $87 CA $99 total Feb 9 - Feb 10 includes taxes & fees 8/10 Very Good! (1,000 reviews) Just finished a wonderful two-week stay and couldn't be happier. The staff was incredibly friendly and welcoming throughout my solo trip. The room was exceptionally clean, quiet, and cozy warm. Added perks like free 24/7 coffee made it perfect. A fantastic experience—would highly recommend. Reviewed on Jan 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=10095&PinnedHotelID=10095&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 15 - Feb 16 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=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=12262&PinnedHotelID=12262&HadPinnedHotel=true®ionId=553248635975855642) [See all 390 properties in Windsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F02%2F2026&endDate=10%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