Title: Windsor Vacation Packages 2026 from $509 | Expedia.com [Windsor Travel Guide](https://expedia.com/Windsor.dx7881)[Hotels in Windsor](https://expedia.com/Windsor-Hotels.d7881.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d7881.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.com/Cheap-Flights-To-Windsor.d7881.Travel-Guide-Flights)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d7881.Car-Rental-Guide) ![](https://images.trvl-media.com/place/7881/cd323da6-a215-45d8-82e1-e1768184197a.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windsor Vacations from $509 ## 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 ## Your Windsor Vacation Food, history, entertainment and more … There's so much to experience with a Windsor vacation package. And with the ability to customize your city break, you know it'll be one that's hard to forget. If sightseeing is on the agenda during your trip to Windsor, stop by leading attractions like [Mount Ascutney](https://www.expedia.com/Mount-Ascutney-Windsor.d553248621532666931.Vacation-Attraction), [Blow-Me-Down Bridge](https://www.expedia.com/Blow-Me-Down-Bridge-Cornish.d553248621532666969.Vacation-Attraction) and [Mt Ascutney State Park](https://www.expedia.com/Mt-Ascutney-State-Park-Vermont.d6175264.Vacation-Attraction). Whoever you're escaping with and whether your budget is big or small, your ultimate Windsor vacation is only clicks away with Expedia. ## The Latest Windsor vacation packages Price found within the past 48 hours. Click for updated prices. ![Jackson Gore Village](https://images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Jackson Gore Village Jackson Gore Base Area $509 per person May 29 - May 31 found 24 hours ago Roundtrip flight included Minneapolis (MSP) to Springfield (VSF) 8.6/10 Excellent! (834 reviews) Clean, staff was great. Reviewed on Dec 23, 2025 ![Treehouse Home in Ludlow](https://images.trvl-media.com/lodging/121000000/120110000/120100200/120100182/815dfdc4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Treehouse Home in Ludlow $1,509 per person May 29 - May 31 found 24 hours ago Roundtrip flight included Minneapolis (MSP) to Springfield (VSF) No reviews ![The Hartness House](https://images.trvl-media.com/lodging/10000000/9720000/9715200/9715200/299bcb43_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Hartness House $612 per person May 29 - May 31 found 24 hours ago Roundtrip flight included Minneapolis (MSP) to Springfield (VSF) 8.2/10 Very Good! (328 reviews) So be aware, YOU ARE PROBABLY NOT SLEEPING IN THE BEAUTIFUL MANSION. There is long ugly gray motel in the back, where the rooms actually are. Our host was lovely on check in & I kinda feel bad for this tepid review but as our friend said "this place has all the charm of a upscale Motel 6". Our room was clean & ok for a nights sleep though & the price was right for us. Room 24's bed had the DREADED "constantly roll into the middle of the mattress" SWALE in it, our friends said, so maybe they could replace that. The motel connects to the mansion & your are kindly told you can come, "check it out at night & in the morning there is continental breakfast & coffee" here. I actually wish they opened the beautiful bar on the weekend so we could have sat there & had a drink instead of going back to the Motel 6\. Anyway, it was fine, but not exactly what we expected. Reviewed on Feb 10, 2026 ![Winterplace at Okemo, A Vail Resorts Property](https://images.trvl-media.com/lodging/13000000/12530000/12522700/12522689/58a46b66_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Winterplace at Okemo, A Vail Resorts Property Clock Tower Base Area $543 per person May 29 - May 31 found 24 hours ago Roundtrip flight included Minneapolis (MSP) to Springfield (VSF) 8.8/10 Excellent! (26 reviews) The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty Reviewed on Dec 1, 2025 ![Deer Brook Inn ](https://images.trvl-media.com/lodging/123000000/122650000/122648800/122648718/53db29c8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Deer Brook Inn $555 per person May 29 - May 31 found 24 hours ago Roundtrip flight included Minneapolis (MSP) to Springfield (VSF) No reviews 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/2026-04-03/2026-04-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=VSF&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_7881) ### Discover the most popular places to visit in Windsor ![La rivière Otter Creek pour aller à Vergennes, Vermont.](https://images.trvl-media.com/place/553248621532666970/0b6ecb17-7da3-48e6-a4c6-9908a628f235.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Paradise Park 4/5(4 reviews) Explore the great outdoors at Paradise Park, a lovely green space in Windsor. Wander the riverfront in this quaint area. [](https://expedia.com/Paradise-Park-Windsor.d553248621532666970.Vacation-Attraction) ![Bowers Covered Bridge - Vermont](https://images.trvl-media.com/place/553248621532666963/0aea9e2a-d801-4d4d-8059-76669d528621.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Brownsville Trail You can take time to visit Brownsville Trail during your travels to Windsor. Discover the mountain views in this family-friendly area, or seek out the ski slopes. [](https://expedia.com/Brownsville-Trail-Windsor.d553248621532666963.Vacation-Attraction) #### American Precision Museum You can spend time exploring the galleries in American Precision Museum in Windsor. Wander the riverfront in this quaint area. [](https://expedia.com/American-Precision-Museum-Windsor.d6330768.Vacation-Attraction) ## Windsor Hotel Deals ![Killington Mountain Lodge, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/403a8548_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Killington Mountain Lodge, Tapestry Collection by Hilton 2617 Killington Rd Killington VT $188 nightly $207 total Apr 1 - Apr 2 Total with taxes and fees 7.4/10 Good! (1,006 reviews) Room was clean. Hotel was clean. Enjoyed my stay Reviewed on Mar 2, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F1%2F2026&endDate=4%2F2%2F2026&selected=103640&PinnedHotelID=103640&HadPinnedHotel=true®ionId=7881) ![Align Inn Vermont](https://images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Align Inn Vermont 5817 Woodstock Rd Quechee VT $108 nightly $119 total Mar 8 - Mar 9 Total with taxes and fees 9.4/10 Exceptional! (1,131 reviews) Perfection in every way Reviewed on Mar 1, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%2F2026&selected=1108&PinnedHotelID=1108&HadPinnedHotel=true®ionId=7881) ![Fireside Inn & Suites West Lebanon](https://images.trvl-media.com/lodging/1000000/20000/12300/12300/adb27d13_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Fireside Inn & Suites West Lebanon 25 Airport Road West Lebanon NH Fully refundableReserve now, pay when you stay $143 nightly $156 total Mar 4 - Mar 5 Total with taxes and fees 8.2/10 Very Good! (1,006 reviews) False Advertising. There was no breakfast Reviewed on Mar 2, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F4%2F2026&endDate=3%2F5%2F2026&selected=12300&PinnedHotelID=12300&HadPinnedHotel=true®ionId=7881) [See all 2,693 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F4%2F2026&endDate=3%2F5%2F2026®ionId=7881) 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 | Lebanon Municipal Airport (LEB) | | Population | 2,100 | | Max Temp Winter | 25ºF | | Max Temp Summer | 75ºF | | Top Sights | [Mt Ascutney State Park](https://www.expedia.com/Mt-Ascutney-State-Park-Vermont.d6175264.Vacation-Attraction), [Harpoon Brewery](https://www.expedia.com/Harpoon-Brewery-Windsor.d553248635975913439.Vacation-Attraction) and [Quechee State Park](https://www.expedia.com/Quechee-State-Park-Quechee.d553248621532667673.Vacation-Attraction) | ## 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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Windsor vacation package cost? ### What are the cheapest months to go to Windsor? ### How many days is enough for Windsor? ### Is it worth booking a vacation package to Windsor? ### How to find the best Windsor package deals? ### Is it cheaper to book a Windsor vacation as a package? ### When to book a vacation package to Windsor? ### Does Expedia offer Book Now, Pay Later Windsor vacation packages? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app