Title: Windsor Vacation Packages 2026 from $474 | 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 $474 ## 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 $474 per person May 7 - May 10 found 14 hours ago Roundtrip flight included Nashville (BNA) to Augusta (AUG) 8/10 Very Good! (1,002 reviews) Such a nice quiet stay. Beautiful location. Grateful for the friendly customer service as well. Amazing value. Reviewed on Apr 4, 2026 ![Spruce Point Inn](https://images.trvl-media.com/lodging/1000000/900000/893300/893209/76da18d6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Spruce Point Inn $980 per person May 22 - May 25 found 4 hours ago Roundtrip flight included New York (NYC) to Augusta (AUG) 8.8/10 Excellent! (397 reviews) didn't have breakfast but view was amazing Reviewed on Oct 23, 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 $552 per person May 7 - May 10 found 14 hours ago Roundtrip flight included Nashville (BNA) to Augusta (AUG) 9.4/10 Exceptional! (916 reviews) Clean room, friendly staff, in walking distance to everything great view Reviewed on Mar 20, 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 $1,795 per person Jun 21 - Jun 26 found 8 hours ago Roundtrip non-stop flight included Nashville (BNA) to Augusta (AUG) 9.2/10 Wonderful! (15 reviews) Our host is the best! Such a beautiful property. Reviewed on Nov 16, 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 $702 per person May 22 - May 25 found 4 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 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/2026-05-05/2026-05-12/?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 12 - Apr 13 Total with taxes and fees 9.2/10 Wonderful! (1,001 reviews) Good Reviewed on Apr 4, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%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 $112 nightly $122 total Apr 6 - Apr 7 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%2F6%2F2026&endDate=4%2F7%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 $93 nightly $101 total May 3 - May 4 Total with taxes and fees 8.6/10 Excellent! (890 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=5%2F3%2F2026&endDate=5%2F4%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%2F6%2F2026&endDate=4%2F7%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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