Title: Windsor Vacation Packages 2026 from $514 | 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 $514 ## 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 $514 per person May 22 - May 25 found 1 day ago Roundtrip flight included Nashville (BNA) 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 $1,506 per person May 15 - May 22 found 6 hours ago Roundtrip non-stop flight included Minneapolis (MSP) 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 $833 per person Apr 17 - Apr 22 found 1 day ago Roundtrip flight included Boston (BOS) to Augusta (AUG) 9.4/10 Exceptional! (914 reviews) The location was perfect, rooms were clean and waitstaff was courteous. Reviewed on Feb 22, 2026 ![210 Main St](https://images.trvl-media.com/lodging/111000000/110800000/110790100/110790062/4348112c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 210 Main St $865 per person May 15 - May 22 found 6 hours ago Roundtrip non-stop flight included Minneapolis (MSP) 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 ![OneSixtyFive](https://images.trvl-media.com/lodging/83000000/82450000/82442000/82441910/16b08991_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### OneSixtyFive $700 per person Apr 16 - Apr 19 found 1 day ago Roundtrip non-stop flight included Dallas (DFW) to Augusta (AUG) 9.4/10 Exceptional! (147 reviews) Clean, quiet, and comfortable. Very nice setting in the carriage house, enjoyable stay. Reviewed on Nov 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/2026-04-08/2026-04-15/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=AUG&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_175568) ## 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 $106 nightly $116 total Mar 19 - Mar 20 Total with taxes and fees 9.2/10 Wonderful! (1,006 reviews) Everything was excellent at this hotel. The staff was very accommodating and pleasantly very helpful at all times Reviewed on Mar 6, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F19%2F2026&endDate=3%2F20%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 $104 nightly $113 total Mar 9 - Mar 10 Total with taxes and fees 7.8/10 Good! (1,004 reviews) BothThe hot tub and saunas were out of commission so we did not have access to these, very disappointing. Reviewed on Mar 6, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F9%2F2026&endDate=3%2F10%2F2026&selected=9853&PinnedHotelID=9853&HadPinnedHotel=true®ionId=175568) ![Homewood Suites by Hilton Augusta](https://images.trvl-media.com/lodging/16000000/15600000/15591900/15591820/3f18ff2e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Homewood Suites by Hilton Augusta 377 Western Avenue Augusta ME Fully refundableReserve now, pay when you stay $131 nightly $142 total Mar 22 - Mar 23 Total with taxes and fees 9.2/10 Wonderful! (1,001 reviews) Very disappointed with water pressure and the fact that the shower head barely spit out water. There was no body wash in shower. The container was complete missing from the holder tied to wall. Also upon check in waited behind another couple as we stood there and there was no one around working the ... Reviewed on Feb 27, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=15591820&PinnedHotelID=15591820&HadPinnedHotel=true®ionId=175568) [See all 655 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F9%2F2026&endDate=3%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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