Title: Windsor Vacation Packages 2026 from $660 | 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 $660 ## 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. ![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 $660 per person Jun 26 - Jun 29 found 10 hours ago Roundtrip non-stop flight included Cleveland (CLE) to Augusta (AUG) 8/10 Very Good! (1,002 reviews) friendly customer service as well. nice quiet stay. Reviewed on Apr 6, 2026 ![Greenleaf Inn](https://images.trvl-media.com/lodging/109000000/108780000/108777400/108777377/eca2d4ec_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Greenleaf Inn $711 per person Jun 26 - Jun 29 found 7 hours ago Roundtrip non-stop flight included Cleveland (CLE) to Augusta (AUG) 9.2/10 Wonderful! (15 reviews) Our host is the best! Such a beautiful property. Reviewed on Nov 16, 2025 ![Linekin Bay Resort](https://images.trvl-media.com/lodging/15000000/14660000/14657800/14657719/47dcf3c2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Linekin Bay Resort $1,036 per person Jun 14 - Jun 19 found 3 hours ago Roundtrip non-stop flight included Dallas (DFW) to Augusta (AUG) 9.2/10 Wonderful! (203 reviews) My wife and I enjoyed our time at the resort. Property is quiet and well maintained. Views are breathtaking and pleasant. Staff were very friendly and pleasant and sought to make sure we had all we needed. Food was spot on! We tried as much as we could that was on the menu and couldn’t find anything we didn’t like and wouldn’t eat again. We jokingly asked each other “do you have anything you didn’t like or would change” and we couldn’t think of anything. Highly recommend and will return if life permits! Reviewed on Oct 1, 2025 ![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 $682 per person Jun 26 - Jun 29 found 23 hours ago Roundtrip non-stop flight included Cleveland (CLE) 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 ![Admirals Quarters Inn](https://images.trvl-media.com/lodging/97000000/96400000/96397200/96397184/246bb89f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Admirals Quarters Inn $801 per person Jun 26 - Jun 29 found 7 hours ago Roundtrip non-stop flight included Cleveland (CLE) to Augusta (AUG) 9.4/10 Exceptional! (30 reviews) The room was great. Lots of space. The bed was super comfortable. The breakfast items were delicious. We enjoyed the many selections of tea and coffee. The proprietor,Jersey was terrific. He explained the property and area Had a wonderful time Reviewed on Dec 1, 2025 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/2026-05-08/2026-05-15/?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 $120 nightly $131 total Apr 16 - Apr 17 Total with taxes and fees 9.2/10 Wonderful! (1,005 reviews) The room itself was clean, but unfortunately, the overall comfort fell short. The bed was particularly strange. It was hard to tell whether it was too soft or too firm, but either way, something just didn’t feel right. It made it difficult to get a comfortable night’s sleep. The pillows also left ... Reviewed on Apr 5, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F16%2F2026&endDate=4%2F17%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 $109 nightly $119 total Apr 26 - Apr 27 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%2F26%2F2026&endDate=4%2F27%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 $96 nightly $105 total Apr 12 - Apr 13 Total with taxes and fees 8.6/10 Excellent! (893 reviews) Nice Reviewed on Apr 8, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=802109&PinnedHotelID=802109&HadPinnedHotel=true®ionId=175568) [See all 662 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=4%2F9%2F2026&endDate=4%2F10%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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