Title: Windsor Vacation Packages & Trips 2026 from CA $722 | Expedia.ca [Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d553248635975850362.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d553248635975850362.Travel-Guide-VacationRentals)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d553248635975850362.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 #### Your Windsor Vacation Take the stress out of organizing your next exciting adventure with a Windsor vacation package. Whether you're lured here by its history, food or other highlights, this city offers endless possibilities for fun. Every trip to Windsor should include a little sightseeing. [Kates Fish Camp](https://www.expedia.ca/Kates-Fish-Camp-Gainesville.d553248621563220062.Vacation-Attraction) is an excellent place to start. No matter your travel plans or budget, organizing a tailored Windsor vacation is a cinch with Expedia. ## Top Windsor Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Westgate Town Center Resort](https://images.trvl-media.com/lodging/1000000/430000/426900/426819/410a3d83_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Westgate Town Center Resort CA $722 per person Feb 17 - Feb 24 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Orlando (MCO) 8/10 Very Good! (1,367 reviews) La habitacion muy buena y limpia expaciosa recomendaria cambiar ollas y sartenes estan muy viejos y quemados Reviewed on Dec 4, 2025 ![Florida Hotel & Conference Center in the Florida Mall](https://images.trvl-media.com/lodging/1000000/20000/17800/17739/3ccef447_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Florida Hotel & Conference Center in the Florida Mall CA $852 per person Feb 17 - Feb 24 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Orlando (MCO) 9.2/10 Wonderful! (2,232 reviews) Fantastic room, excellent dining options, free parking, helpful staff, excellent pools Reviewed on Dec 16, 2025 ![The Delaney Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19389600/19389598/ceba7f1d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Delaney Hotel South Orange CA $1,157 per person Feb 17 - Feb 24 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Orlando (MCO) 9.6/10 Exceptional! (1,002 reviews) We had a great one-night stay for the Matt Rife show at Kia Center. Ride Share options were plentiful, room was clean and staff was very friendly and helpful! Breakfast at the tavern was delicious and the complimentary coffee was a bonus! The noise from emergency vehicles and helicopter landing and taking off was noticeable but not terrible and to be expected across from the hospital. We felt fortunate to stay for an event and had empathy for those pacing the floors of the hospital across the street. Whatever brings you there, it's a lovely place to stay. Reviewed on Dec 16, 2025 ![Margaritaville Cottages Orlando with H2O Waterpark by Vstays](https://images.trvl-media.com/lodging/36000000/35110000/35109100/35109061/0a506e54_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Margaritaville Cottages Orlando with H2O Waterpark by Vstays CA $1,572 per person Feb 17 - Feb 24 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Orlando (MCO) 9.2/10 Wonderful! (1,001 reviews) The place was really nice, with plenty of room for everyone. But, the normal amenities were lacking. They would not provide extra towels, hand soap, toilet paper, etc., etc!! We called several times about heating the hot tub; we were told there was nothing they could do about it. There was a coffee machine, but no filters, coffee,etc. We were NOT going for a week vacation, so would not expect to have to buy such things for just a couple days stay. So, it's sad that the little things can ruin the overall family time! Reviewed on Dec 16, 2025 ![Ocean Sands Beach Boutique Inn - 1 Acre Private Beach](https://images.trvl-media.com/lodging/1000000/810000/809000/808920/65d99be5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ocean Sands Beach Boutique Inn - 1 Acre Private Beach Vilano Beach CA $944 per person Feb 21 - Feb 28 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Orlando (MCO) 8.8/10 Excellent! (645 reviews) Very clean and courteous staff! Reviewed on Dec 14, 2025 ## Ready to book your vacation to Windsor? Choose your dates ## Windsor Hotel Deals ![Hilton University of Florida Conference Center Gainesville](https://images.trvl-media.com/lodging/1000000/480000/475300/475205/7dbdcf15_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton University of Florida Conference Center Gainesville 1714 SW 34th St Gainesville FL Fully refundableReserve now, pay when you stay CA $133 CA $150 total Dec 24 - Dec 25 includes taxes & fees 8.2/10 Very Good! (1,002 reviews) The room, location, and staff were perfect. The only reason it didn't receive five stars is that if you are staying for a day and there is an event or conference, it may be impossible to find parking. The morning food option in the cafe was lackluster. Reviewed on Dec 8, 2025 [](https://expedia.ca/Hotel-Search?startDate=24%2F12%2F2025&endDate=25%2F12%2F2025&selected=475205&PinnedHotelID=475205&HadPinnedHotel=true®ionId=553248635975850362) ![Hotel Eleo at the University of Florida](https://images.trvl-media.com/lodging/53000000/52060000/52054200/52054135/180700a0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Eleo at the University of Florida 1514 Southwest 14th Street Gainesville FL Fully refundableReserve now, pay when you stay CA $153 CA $172 total Dec 21 - Dec 22 includes taxes & fees 9.2/10 Wonderful! (1,285 reviews) Relatively new hotel staffed with several recent graduates of the University of Florida. Reviewed on Dec 12, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&selected=52054135&PinnedHotelID=52054135&HadPinnedHotel=true®ionId=553248635975850362) ![DoubleTree by Hilton Gainesville](https://images.trvl-media.com/lodging/1000000/50000/49700/49617/ff7eaa86_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Gainesville 3726 Sw 40th Blvd Gainesville FL Fully refundableReserve now, pay when you stay CA $112 CA $126 total Dec 24 - Dec 25 includes taxes & fees 7.6/10 Good! (1,000 reviews) Our overall stay was good. At first I was taken aback from the front desk and how one young lady talked her guest as opposed to how my front desk staff talked to me. I chalked it up to young kids. The room was ok. Found some pet hair and women hair on the carpet. Need to do a better job of Cleaning. ... Reviewed on Dec 8, 2025 [](https://expedia.ca/Hotel-Search?startDate=24%2F12%2F2025&endDate=25%2F12%2F2025&selected=49617&PinnedHotelID=49617&HadPinnedHotel=true®ionId=553248635975850362) [See all 823 properties in Windsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=18%2F12%2F2025&endDate=19%2F12%2F2025®ionId=553248635975850362) 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 #### Shands at the University of Florida Though Shands at the University of Florida might be what brings you to town, perhaps you'll have a chance to explore more of Gainesville while you are here. [](https://expedia.ca/Shands-At-The-University-Of-Florida-Gainesville.d6187967.Vacation-Attraction) #### North Florida Regional Medical Center Though North Florida Regional Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Gainesville while you are here. [](https://expedia.ca/North-Florida-Regional-Medical-Center-Gainesville.d6187962.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