Title: Windsor Vacation Packages 2026 from $616 | 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 $616 ## 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. ![The Covered Bridge Inn](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Covered Bridge Inn $616 per person Mar 19 - Mar 22 found 1 day ago Roundtrip non-stop flight included Minneapolis (MSP) to Springfield (VSF) 7.6/10 Good! (1,002 reviews) Easy check in and good parking Reviewed on Jan 9, 2026 ![Okemo Mountain Lodging](https://images.trvl-media.com/lodging/33000000/32350000/32342000/32341945/05713f89_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Okemo Mountain Lodging Clock Tower Base Area $1,830 per person Mar 19 - Mar 22 found 1 day ago Roundtrip non-stop flight included Minneapolis (MSP) to Springfield (VSF) 7.8/10 Good! (28 reviews) Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June. Reviewed on Jun 26, 2025 ![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 $1,333 per person Mar 19 - Mar 22 found 1 day ago Roundtrip non-stop flight included Minneapolis (MSP) to Springfield (VSF) 8.6/10 Excellent! (834 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/f814b3d5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Stone Hearth Inn and Eatery $769 per person Mar 19 - Mar 22 found 1 day ago Roundtrip non-stop flight included Minneapolis (MSP) to Springfield (VSF) 9.2/10 Wonderful! (106 reviews) So great all around! Reviewed on Jan 4, 2026 ![Mountain Lodge at Okemo](https://images.trvl-media.com/lodging/3000000/2420000/2417100/2417011/5263ccb3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Mountain Lodge at Okemo Clock Tower Base Area $992 per person Mar 19 - Mar 22 found 1 day ago Roundtrip non-stop flight included Minneapolis (MSP) to Springfield (VSF) 8/10 Very Good! (219 reviews) We really enjoyed our stay at the Mountain Lodge at Okemo, it was clean and our room was newly renovated and very cute. Would definitely recommend!! Reviewed on Oct 6, 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/2026-03-06/2026-03-13/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=VSF&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Windsor ![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) ![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 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) #### 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 Fully refundableReserve now, pay when you stay $156 nightly $172 total Mar 1 - Mar 2 Total with taxes and fees 7.2/10 Good! (1,000 reviews) Close to the resort, nice hot tub, decent room with a modern tv software for easy connections. Good price to hotel quality ratio. Reviewed on Jan 26, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%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 $120 nightly $132 total Feb 8 - Feb 9 Total with taxes and fees 9.4/10 Exceptional! (1,100 reviews) Clean room, nice breakfast, nice restaurant next door Reviewed on Feb 1, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F8%2F2026&endDate=2%2F9%2F2026&selected=1108&PinnedHotelID=1108&HadPinnedHotel=true®ionId=7881) ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pointe at Castle Hill Resort 2940 State Route 103 Cavendish VT $142 nightly $154 total Mar 3 - Mar 4 Total with taxes and fees 8.8/10 Excellent! (970 reviews) Clean room! Great food! Reviewed on Jan 30, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F3%2F2026&endDate=3%2F4%2F2026&selected=1823093&PinnedHotelID=1823093&HadPinnedHotel=true®ionId=7881) [See all 2,693 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F7%2F2026&endDate=2%2F8%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://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