Title: Windsor Vacation Packages 2026 from $290 | Expedia.com [Hotels in Windsor](https://expedia.com/Windsor-Hotels.d553248635740535086.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d553248635740535086.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.com/Cheap-Flights-To-Windsor.d553248635740535086.Travel-Guide-Flights)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d553248635740535086.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 Vacations from $290 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 a city stay is calling, answer it with a Windsor vacation package. With all your travel needs in place before you leave, all you have to do here is concentrate on having fun. Every trip to Windsor should include a little sightseeing. [le Parc Historique de la Poudriere de Windsor](https://www.expedia.com/Le-Parc-Historique-De-La-Poudriere-De-Windsor-Windsor.d553248621532865870.Vacation-Attraction) is a superb place to kick off your exploring. Your Windsor vacation is just a few clicks away. Browse airfares, hotels and more on Expedia for a trip that's tailored to suit your travel style. ## The Latest Windsor vacation packages Price found within the past 48 hours. Click for updated prices. ![Rio Hotel & Casino, a Destination by Hyatt Hotel](https://images.trvl-media.com/lodging/1000000/20000/19900/19837/w2160h1608x0y0-e07688de_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Rio Hotel & Casino, a Destination by Hyatt Hotel Save 100% on your flight $290 per person Mar 31 - Apr 3 found 1 day ago Roundtrip flight included Boston (BOS) to Las Vegas (LAS) 7.8/10 Good! (6,684 reviews) Clean and comfortable the nicest room we have ever stayed in. The room was cleaned each day Quiet and never heard anything noises while in the room. Easy to park and enter the casino. Will pass this on to our family and friends. Reviewed on Feb 28, 2026 ![Casablanca Miami Beach](https://images.trvl-media.com/lodging/32000000/31660000/31652200/31652150/628e521a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Casablanca Miami Beach North Beach $2,058 per person May 18 - May 22 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 5.8/10 (311 reviews) Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it. Reviewed on Feb 22, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach $5,263 per person May 23 - May 26 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ![One Bedroom | 1.5 Baths & Living Room | Jet Tub – Palms Place StripSuite](https://images.trvl-media.com/lodging/118000000/117360000/117352700/117352668/e2fb1771_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### One Bedroom | 1.5 Baths & Living Room | Jet Tub – Palms Place StripSuite $4,990 per person May 1 - May 8 found 5 hours ago Roundtrip flight included Boston (BOS) to Las Vegas (LAS) 10/10 Exceptional! (1 review) Staff was awesome and helpful Reviewed on Sep 2, 2025 ![NobleDEN Hotel](https://images.trvl-media.com/lodging/9000000/8690000/8682300/8682234/cb1dc844_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### NobleDEN Hotel Manhattan $1,261 per person May 1 - May 8 found 1 day ago Roundtrip flight included Boston (BOS) to Newark Liberty Intl. Airport (EWR) 9.8/10 Exceptional! (1,411 reviews) Room is very clean. Staff are nice. Superb location. I’ll definitely consider to stay here again Reviewed on Feb 27, 2026 Don't see what you're looking for? See all available trips from Columbus to Windsor [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-01/2026-04-08/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=YSC&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_553248635740535086) ### Discover the most popular places to visit in Windsor #### le Parc Historique de la Poudriere de Windsor Find out about the history of Windsor with a stop at le Parc Historique de la Poudriere de Windsor. You can enjoy the restaurants while in the area. [](https://expedia.com/Le-Parc-Historique-De-La-Poudriere-De-Windsor-Windsor.d553248621532865870.Vacation-Attraction) ## Windsor Hotel Deals ![Manoir des Sables Hôtel & Golf](https://images.trvl-media.com/lodging/2000000/1810000/1807000/1806928/c0bb21b9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Manoir des Sables Hôtel & Golf 90 Des Jardins Ave. Orford QC Fully refundableReserve now, pay when you stay $79 nightly $94 total Mar 22 - Mar 23 Total with taxes and fees 8.4/10 Very Good! (1,267 reviews) Loved the room. We got a suite and it was absolutely wonderful. Fireplace in the room with logs provided. Wonderful. The hot tubs / pool area were somewhat smaller / outdated. Reviewed on Feb 28, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=1806928&PinnedHotelID=1806928&HadPinnedHotel=true®ionId=553248635740535086) ![OTL Gouverneur Sherbrooke](https://images.trvl-media.com/lodging/19000000/18970000/18964300/18964290/ac5cb70b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### OTL Gouverneur Sherbrooke 3131 rue King Ouest Sherbrooke QC Fully refundableReserve now, pay when you stay $161 nightly $191 total Mar 8 - Mar 9 Total with taxes and fees 9.8/10 Exceptional! (1,691 reviews) Amazing Reviewed on Feb 26, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%2F2026&selected=18964290&PinnedHotelID=18964290&HadPinnedHotel=true®ionId=553248635740535086) ![Grand Times Hotel Sherbrooke](https://images.trvl-media.com/lodging/4000000/3610000/3604700/3604686/7bf9aa07_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Grand Times Hotel Sherbrooke 1, rue Belvedere Sud Sherbrooke QC Fully refundableReserve now, pay when you stay $155 nightly $184 total Mar 2 - Mar 3 Total with taxes and fees 8.4/10 Very Good! (1,004 reviews) Good Reviewed on Feb 24, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F2%2F2026&endDate=3%2F3%2F2026&selected=3604686&PinnedHotelID=3604686&HadPinnedHotel=true®ionId=553248635740535086) [See all 174 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F2%2F2026&endDate=3%2F3%2F2026®ionId=553248635740535086) 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. ## Find the Best Windsor Vacation Packages ## Windsor Essential Information | Language | English | | ---------- | ---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | Canadian dollars | | Population | 5,400 | | Top Sights | [Centre dInterpretation de lArdoise](https://www.expedia.com/Centre-DInterpretation-De-LArdoise-Richmond.d553248621532865863.Vacation-Attraction), [Centre dInterprétation de lHistoire de Sherbrooke](https://www.expedia.com/Centre-DInterpretation-De-LHistoire-De-Sherbrooke-Sherbrooke.d553248621533087852.Vacation-Attraction) and [Sherbrooke Golf Club](https://www.expedia.com/Sherbrooke-Golf-Club-Sherbrooke.d553248621561106018.Vacation-Attraction) | ## More vacations you might like ![](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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.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.com/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.com/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.com/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.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Windsor vacation package cost? ### What are the cheapest months to go to Windsor? ### How many days is enough for Windsor? ### How to find the best Windsor package deals? ### Is it cheaper to book a Windsor vacation as a package? ### When to book a vacation package to Windsor? ### Does Expedia offer Book Now, Pay Later Windsor vacation packages? \* 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 even more - get up to 20% on select hotels 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