Title: Windsor Vacation Packages & Trips 2026 from CA $853 | Expedia.ca [Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d175568.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d175568.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.ca/Cheap-Flights-To-Windsor.d175568.Travel-Guide-Flights)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d175568.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 ## Top Windsor Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Maine Evergreen Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/790000/787600/787572/42d3f26f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Maine Evergreen Hotel, an Ascend Collection Hotel CA $853 per person Mar 13 - Mar 18 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Augusta (AUG) 9.2/10 Wonderful! (1,000 reviews) The room was clean. The staff was extremely pleasant. The hotel was really nice; I loved the gallery feel to it. Reviewed on Dec 29, 2025 ![Comfort Inn Ellsworth - Bar Harbor](https://images.trvl-media.com/lodging/1000000/10000/9900/9881/9809a150_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Comfort Inn Ellsworth - Bar Harbor CA $1,150 per person Feb 13 - Feb 16 found 10 hours ago Roundtrip flight included Calgary (YYC) to Augusta (AUG) 9/10 Wonderful! (879 reviews) Room was clean. Bed was a bit too soft. Check in person was quite helpful with respect to the area's amenities. Reviewed on Dec 22, 2025 ![210 Main St](https://images.trvl-media.com/lodging/111000000/110800000/110790100/110790062/cb9b5cad_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 210 Main St CA $1,240 per person Feb 13 - Feb 16 found 10 hours ago Roundtrip flight included Calgary (YYC) to Augusta (AUG) 9/10 Wonderful! (10 reviews) Such a cool place to stay. Love the history of the building yet had modern amenities. Good location. Reviewed on Oct 17, 2025 ![Colonial Inn Ellsworth](https://images.trvl-media.com/lodging/1000000/90000/84600/84589/efa98278_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Colonial Inn Ellsworth CA $1,115 per person Feb 13 - Feb 16 found 10 hours ago Roundtrip flight included Calgary (YYC) to Augusta (AUG) 7.6/10 Good! (827 reviews) staff were helpful and clean rooms Reviewed on Dec 25, 2025 ![The Brunswick Hotel](https://images.trvl-media.com/lodging/5000000/4450000/4449200/4449120/3ba35403_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Brunswick Hotel CA $1,352 per person Feb 13 - Feb 16 found 10 hours ago Roundtrip flight included Calgary (YYC) to Augusta (AUG) 9.4/10 Exceptional! (868 reviews) Everything was great! Reviewed on Dec 15, 2025 ## Ready to book your vacation to Windsor? Choose your dates ## Windsor Hotel Deals ![Maine Evergreen Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/790000/787600/787572/42d3f26f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Maine Evergreen Hotel, an Ascend Collection Hotel 65 Whitten Rd Augusta ME Fully refundable CA $160 CA $174 total Jan 9 - Jan 10, 2026 includes taxes & fees 9.2/10 Wonderful! (1,008 reviews) Clean & nicely decorated room & hotel. Reviewed on Dec 21, 2025 [](https://expedia.ca/Hotel-Search?startDate=09%2F01%2F2026&endDate=10%2F01%2F2026&selected=787572&PinnedHotelID=787572&HadPinnedHotel=true®ionId=175568) ![Senator Inn & Spa](https://images.trvl-media.com/lodging/1000000/10000/9900/9853/19df0ad9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Senator Inn & Spa 284 Western Ave Augusta ME Fully refundableReserve now, pay when you stay CA $126 CA $138 total Jan 18 - Jan 19, 2026 includes taxes & fees 7.8/10 Good! (1,000 reviews) Pleasant front desk check in Reviewed on Dec 15, 2025 [](https://expedia.ca/Hotel-Search?startDate=18%2F01%2F2026&endDate=19%2F01%2F2026&selected=9853&PinnedHotelID=9853&HadPinnedHotel=true®ionId=175568) ![Fireside Inn & Suites Waterville](https://images.trvl-media.com/lodging/1000000/20000/19700/19607/0fbc096a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Fireside Inn & Suites Waterville 376 Main Street Waterville ME Fully refundableReserve now, pay when you stay CA $143 CA $156 total Dec 30 - Dec 31 includes taxes & fees 8.6/10 Excellent! (1,001 reviews) We stayed Christmas Eve and they gave us a little gift bag which was so nice!! The bed was amazing and want to know where to get the mattress. Didn’t have breakfast. For being so close to the Highway I did not hear any noise. Reviewed on Dec 26, 2025 [](https://expedia.ca/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=19607&PinnedHotelID=19607&HadPinnedHotel=true®ionId=175568) [See all 645 properties in Windsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=30%2F12%2F2025&endDate=31%2F12%2F2025®ionId=175568) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. 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