Title: Windsor Vacation Packages 2026 from $856 | 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 $856 ## Book a Hotel + Flight or Car together to unlock savings ## 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, A Vail Resorts Property](https://images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Jackson Gore Village, A Vail Resorts Property Jackson Gore Base Area $856 per person May 5 - May 11 found 4 hours ago Roundtrip non-stop flight included Newark Liberty Intl. Airport (EWR) to Springfield (VSF) 8.6/10 Excellent! (846 reviews) Clean, staff was great. Reviewed on Dec 23, 2025 ![Stone Hearth Inn and Eatery](https://images.trvl-media.com/lodging/88000000/87490000/87486300/87486236/52ce2be1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Stone Hearth Inn and Eatery $989 per person May 5 - May 11 found 4 hours ago Roundtrip non-stop flight included Newark Liberty Intl. Airport (EWR) to Springfield (VSF) 9.2/10 Wonderful! (115 reviews) Great stay! Very cozy and homey. Very yummy breakfast! Reviewed on Feb 27, 2026 ![Treehouse Home in Ludlow](https://images.trvl-media.com/lodging/121000000/120110000/120100200/120100182/e339d32d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Treehouse Home in Ludlow Save 100% on your flight $3,310 per person May 5 - May 11 found 4 hours ago Roundtrip non-stop flight included Newark Liberty Intl. Airport (EWR) to Springfield (VSF) No reviews ![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 $964 per person May 5 - May 11 found 4 hours ago Roundtrip non-stop flight included Newark Liberty Intl. Airport (EWR) 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 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/2026-04-12/2026-04-19/?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/f9bd2dd9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Killington Mountain Lodge, Tapestry Collection by Hilton 2617 Killington Rd Killington VT Fully refundableReserve now, pay when you stay $147 nightly $161 total Apr 9 - Apr 10 Total with taxes and fees 7.4/10 Good! (1,001 reviews) Great place! Close to the mountain and restaurants on access road. Reviewed on Mar 12, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F9%2F2026&endDate=4%2F10%2F2026&selected=103640&PinnedHotelID=103640&HadPinnedHotel=true®ionId=7881) ![White River Inn and Suites](https://images.trvl-media.com/lodging/1000000/30000/28000/27933/ba27b41f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### White River Inn and Suites 91 Ballardvale Drive White River Junction VT Fully refundableReserve now, pay when you stay $121 nightly $133 total Mar 22 - Mar 23 Total with taxes and fees 7/10 Good! (1,002 reviews) Conditions of room was nice and roomy, temperature was perfect Reviewed on Mar 11, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=27933&PinnedHotelID=27933&HadPinnedHotel=true®ionId=7881) ![Align Inn Vermont](https://images.trvl-media.com/lodging/1000000/10000/1200/1108/4cc53d97_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Align Inn Vermont 5817 Woodstock Rd Quechee VT Fully refundableReserve now, pay when you stay $119 nightly $131 total Mar 15 - Mar 16 Total with taxes and fees 9.4/10 Exceptional! (1,136 reviews) Clean room Reviewed on Mar 11, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%2F2026&selected=1108&PinnedHotelID=1108&HadPinnedHotel=true®ionId=7881) [See all 2,685 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F13%2F2026&endDate=3%2F14%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) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf 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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.