Title: Windsor Vacation Packages 2026 from $348 | 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 $348 ## 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. ![Masquerade Tower at Rio Hotel & Casino](https://images.trvl-media.com/lodging/115000000/114900000/114898100/114898093/w1870h1500x115y0-29e4f340_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Masquerade Tower at Rio Hotel & Casino Save 100% on your flight $348 per person Apr 17 - Apr 21 found 1 day ago Roundtrip non-stop flight included Boston (BOS) to Las Vegas (LAS) 7.6/10 Good! (1,656 reviews) Place was nice but very old , the carpets had cigarette burns on the floor. The bathroom had major water problems, leaks also the shower mold I have pictures and videos to prove it too 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 $2,064 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 ![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 11 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) Spacious room, clean, affordable, great location, amazing staff, 10/10 and would stay here again. Mattress and pillows could be little comfier but you can’t have it all lol. So glad we found this place! Reviewed on Mar 1, 2026 ![Hollywood Inn Suites Hotel](https://images.trvl-media.com/lodging/28000000/27240000/27238100/27238098/918a7f8f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hollywood Inn Suites Hotel Save 100% on your flight $452 per person May 23 - May 27 found 1 day ago Roundtrip flight included Boston (BOS) to Los Angeles (LAX) 8.2/10 Very Good! (1,622 reviews) Room was clean and the staff were very nice and helpful. We end up extending another night. Reviewed on Feb 28, 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 $156 nightly $186 total Mar 15 - Mar 16 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%2F15%2F2026&endDate=3%2F16%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) 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![](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