Title: Windsor Vacation Packages 2026 from $323 | Expedia.com [Hotels in Windsor](https://expedia.com/Windsor-Hotels.d175568.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d175568.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.com/Cheap-Flights-To-Windsor.d175568.Travel-Guide-Flights)[Car Rentals in Windsor](https://expedia.com/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 Vacations from $323 ## 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 ## The Latest Windsor vacation packages Price found within the past 48 hours. Click for updated prices. ![Jordan Hotel](https://images.trvl-media.com/lodging/25000000/24110000/24101000/24100923/1e281804_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Jordan Hotel $323 per person Jun 5 - Jun 7 found 1 day ago Roundtrip flight included New York (NYC) to Augusta (AUG) 8.8/10 Excellent! (493 reviews) Great mini ski vacation. Grandkids and family love the Jordan Hotel!!! Reviewed on Mar 21, 2026 ![OneSixtyFive](https://images.trvl-media.com/lodging/83000000/82450000/82442000/82441910/16b08991_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### OneSixtyFive Save 100% on your flight $723 per person Jun 10 - Jun 15 found 11 hours ago Roundtrip flight included New York (NYC) to Augusta (AUG) 9.4/10 Exceptional! (147 reviews) Wonderful property, quiet comfortable rooms, friendly staff, great location in Brunswick, definitely worth staying for the delicious breakfast too, Reviewed on Mar 12, 2026 ![Smuggler's Cove Inn](https://images.trvl-media.com/lodging/3000000/2130000/2130000/2129923/b7d35423_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Smuggler's Cove Inn $434 per person Jun 5 - Jun 8 found 17 hours ago Roundtrip flight included New York (NYC) to Augusta (AUG) 9/10 Wonderful! (451 reviews) This was an end of season visit. The property, breakfast, and staff couldn’t be nicer. Sadly, pool was closed up for the season along with the restaurant. Dining options were very limited, even in town due to it being post Columbus Day. Reviewed on Oct 23, 2025 ![Flagship Inn and Suites](https://images.trvl-media.com/lodging/1000000/900000/894100/894021/8017bb8a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Flagship Inn and Suites $365 per person Jun 5 - Jun 7 found 1 day ago Roundtrip flight included New York (NYC) to Augusta (AUG) 8/10 Very Good! (1,002 reviews) Clean room great amenities Reviewed on Mar 6, 2026 ![Grand Summit Hotel](https://images.trvl-media.com/lodging/25000000/24110000/24100900/24100888/9d36745e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Grand Summit Hotel $438 per person Jun 5 - Jun 8 found 17 hours ago Roundtrip flight included New York (NYC) to Augusta (AUG) 8.4/10 Very Good! (348 reviews) Easy access to slopes. Reviewed on Mar 23, 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/2026-04-23/2026-04-30/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=AUG&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Windsor Hotel Deals ![Maine Evergreen Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/790000/787600/787572/2b5fab10_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Maine Evergreen Hotel, an Ascend Collection Hotel 65 Whitten Rd Augusta ME Fully refundable $110 nightly $120 total Mar 31 - Apr 1 Total with taxes and fees 9.2/10 Wonderful! (1,002 reviews) Rude Reviewed on Mar 19, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F31%2F2026&endDate=4%2F1%2F2026&selected=787572&PinnedHotelID=787572&HadPinnedHotel=true®ionId=175568) ![Senator Inn & Spa](https://images.trvl-media.com/lodging/1000000/10000/9900/9853/c9f754bc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Senator Inn & Spa 284 Western Ave Augusta ME Fully refundableReserve now, pay when you stay $99 nightly $108 total Apr 1 - Apr 2 Total with taxes and fees 7.8/10 Good! (1,000 reviews) Great all sround Reviewed on Mar 18, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F1%2F2026&endDate=4%2F2%2F2026&selected=9853&PinnedHotelID=9853&HadPinnedHotel=true®ionId=175568) ![Holiday Inn Express & Suites Waterville - North by IHG](https://images.trvl-media.com/lodging/1000000/810000/802200/802109/0b519be7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Express & Suites Waterville - North by IHG 332 Main St Waterville ME Fully refundable $86 nightly $94 total Mar 29 - Mar 30 Total with taxes and fees 8.6/10 Excellent! (888 reviews) Staf are friendly and fast but the room it self could use better up keep there was a stain right next to the bed on the floor the wall paper was falling off the walls and bathroom could of used cocked for the corners looked moldy Reviewed on Mar 15, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=802109&PinnedHotelID=802109&HadPinnedHotel=true®ionId=175568) [See all 661 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F24%2F2026&endDate=3%2F25%2F2026®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. Additional terms may apply. ## Find the Best Windsor Vacation Packages ## Windsor Essential Information | Language | English | | --------------- | ---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Knox County Regional Airport (RKD) | | Population | 2,300 | | Top Sights | [Maine State Museum](https://www.expedia.com/Maine-State-Museum-Augusta.d6181699.Vacation-Attraction), [Johnson Hall](https://www.expedia.com/Johnson-Hall-Gardiner.d553248621532668226.Vacation-Attraction) and [Capitol Park](https://www.expedia.com/Capitol-Park-Augusta.d6181427.Vacation-Attraction) | ## More vacations you might like 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