Title: Windsor Vacation Packages 2026 from $772 | 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 $772 ## 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/28000000/27670000/27661400/27661353/10a69b41_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Covered Bridge Inn $772 per person May 22 - May 25 found 16 hours ago Roundtrip non-stop flight included Chicago (CHI) to Springfield (VSF) 7.6/10 Good! (1,007 reviews) Decent Internet. Room stayed warm. Reviewed on Mar 9, 2026 ![Latchis Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/4c998aa8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Latchis Hotel $825 per person May 22 - May 25 found 16 hours ago Roundtrip non-stop flight included Chicago (CHI) to Springfield (VSF) 8.6/10 Excellent! (853 reviews) Great location, great staff really cool old building with lots of character Reviewed on Mar 8, 2026 ![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 $871 per person May 22 - May 25 found 16 hours ago Roundtrip non-stop flight included Chicago (CHI) to Springfield (VSF) 9.2/10 Wonderful! (115 reviews) Great stay! Very cozy and homey. Very yummy breakfast! Reviewed on Feb 27, 2026 ![Windham Hill Inn](https://images.trvl-media.com/lodging/95000000/94660000/94650100/94650035/ee964e2b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Windham Hill Inn $950 per person May 22 - May 25 found 16 hours ago Roundtrip non-stop flight included Chicago (CHI) to Springfield (VSF) 8.4/10 Very Good! (40 reviews) The Inn is situated near the top of a mountain and surrounded by other hilltops. There are trails that help you to reconnect with nature. Our room was lovely and comfortable. There is a attention to detail in the decor of this establishment which is both delightful and humorous. Reviewed on Jul 11, 2025 ![Chalet 239](https://images.trvl-media.com/lodging/102000000/101290000/101284000/101283909/f7a080fa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chalet 239 $815 per person May 22 - May 25 found 16 hours ago Roundtrip non-stop flight included Chicago (CHI) to Springfield (VSF) 9.4/10 Exceptional! (113 reviews) Parking was right in front of the building. The place was very clean all over. Breakfast was included, they served pastries, bagels, yogurt, etc. Super easy check in process. The Chalet is only about a 5 minute drive from mount snow! So grateful to the staff who texted me to let me know we had left something behind and the room when they went to clean it! Reviewed on Mar 19, 2026 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/2026-04-20/2026-04-27/?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 ![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 $139 nightly $152 total Apr 19 - Apr 20 Total with taxes and fees 7.4/10 Good! (1,002 reviews) Yes Reviewed on Mar 19, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F19%2F2026&endDate=4%2F20%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 $129 nightly $142 total Mar 29 - Mar 30 Total with taxes and fees 7/10 Good! (1,002 reviews) The room had a food smell. There were little black flies in the room. When I notified the desk the gentleman said he would be sure to report it to the proper person. No offer of a discount on the price of the room or even a voucher for a future stay which I never would have used. Not interested in ... Reviewed on Mar 15, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=27933&PinnedHotelID=27933&HadPinnedHotel=true®ionId=7881) ![Fireside Inn & Suites West Lebanon](https://images.trvl-media.com/lodging/1000000/20000/12300/12300/43f4036d_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 $141 nightly $154 total Mar 22 - Mar 23 Total with taxes and fees 8.2/10 Very Good! (1,002 reviews) Very convenient location. Helpful, kind staff. Reviewed on Mar 17, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=12300&PinnedHotelID=12300&HadPinnedHotel=true®ionId=7881) [See all 2,704 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F21%2F2026&endDate=3%2F22%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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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