Title: Windsor Vacation Packages 2026 from $333 | 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 $333 ## 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. ![Newagen Seaside Inn](https://images.trvl-media.com/lodging/9000000/8090000/8082900/8082897/e842ee11_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Newagen Seaside Inn $333 per person May 23 - May 25 found 1 day ago Roundtrip flight included New York (NYC) to Augusta (AUG) 9.4/10 Exceptional! (341 reviews) IT WAS CHARMING AND BEAUTIFUL. The restaurant was wonderful, all the staff was first class, would love to go back. Reviewed on Oct 14, 2025 ![House near Acadia National Park](https://images.trvl-media.com/lodging/79000000/78040000/78037400/78037375/1ec57eda_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### House near Acadia National Park $1,442 per person May 3 - May 10 found 16 hours ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Augusta (AUG) 9.8/10 Exceptional! (24 reviews) My family enjoyed our time at this property. I received a friendly email prior to arrival with clear directions and local recommendations. It is a beautiful house, nicely decorated with comfortable furniture - perfect for relaxing and visiting. We loved the location, it is in a quiet neighborhood with multiple shopping and dining options nearby. It took us about 35 minutes to drive to the Bar Harbor area. Reviewed on Oct 15, 2025 ![The Brunswick Hotel](https://images.trvl-media.com/lodging/5000000/4450000/4449200/4449120/3069046e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Brunswick Hotel $683 per person Jun 4 - Jun 7 found 24 hours ago Roundtrip flight included New York (NYC) to Augusta (AUG) 9.4/10 Exceptional! (916 reviews) Loved our stay! Friendly staff, cozy fireplaces in the lobby, room was clean and comfortable. 5 minute walk from the train station. Highly recommend! Reviewed on Mar 8, 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 $1,082 per person Apr 19 - Apr 22 found 1 hour ago Roundtrip non-stop flight included Minneapolis (MSP) to Augusta (AUG) 9.2/10 Wonderful! (15 reviews) Our host is the best! Such a beautiful property. Reviewed on Nov 16, 2025 ![Colonial Inn Ellsworth](https://images.trvl-media.com/lodging/1000000/90000/84600/84589/223b08fe_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Colonial Inn Ellsworth $777 per person May 3 - May 10 found 16 hours ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Augusta (AUG) 7.6/10 Good! (839 reviews) Staff was helpful and courteous. We enjoyed our stay. Kids enjoyed the Amenities. My only criticism is the towels. Towels are stained and dingy. The entire place was clean despite being outdated. The towels were clean, but that one update would have made my stay even better. Breakfast was grab and go with options everyone could enjoy. Coffee was great. Our family will keep this place in mind for our next trip. Reviewed on Feb 16, 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/2026-04-17/2026-04-24/?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 $107 nightly $117 total Mar 26 - Mar 27 Total with taxes and fees 9.2/10 Wonderful! (1,005 reviews) Everything was fantastic Reviewed on Mar 17, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F26%2F2026&endDate=3%2F27%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 Mar 23 - Mar 24 Total with taxes and fees 7.8/10 Good! (1,003 reviews) Children are “allowed” but I would NOT recommend staying here with them. The pool is “for the spa”, the staff were aggressive and rude and I will never return here. Absolutely awful experience here with my children. Reviewed on Mar 16, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F23%2F2026&endDate=3%2F24%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 22 - Mar 23 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%2F22%2F2026&endDate=3%2F23%2F2026&selected=802109&PinnedHotelID=802109&HadPinnedHotel=true®ionId=175568) [See all 658 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F18%2F2026&endDate=3%2F19%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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