Title: Windsor Vacation Packages 2026 from $777 | 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 $777 ## 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. ![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 $777 per person May 8 - May 11 found 18 hours ago Roundtrip flight included Grand Rapids (GRR) to Springfield (VSF) 8.6/10 Excellent! (853 reviews) If you love retro/vintage/history/ quiet and pet friendly this place is wonderful for a short stay and lowkey weekend. So many cool local businesses and delicious food. We went for a show at the stone church- walking distance from hotel! And everything we could have needed was easily accessible. They have a bar downstairs and a movie theatre in the hotel! All rooms have record players and vinyls to play with more available. Big rooms. “Dated” but it’s keeping with the retro style- very clean and neat. Only negatives were the parking lot (really small but we got a spot! There’s plenty of on street parking and a nearby parking garage as well). Staff was so friendly and helpful! This would be a great “staycation” or mom night away as well. Stop at some of the amazing thrift/vintage/2nd hand stores for books, music, clothes and more. If you’re a crafter, Bobbins’and Skeins and Beadnik are great places to take a look at. I’d definitely come back! Reviewed on Mar 30, 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 $877 per person May 8 - May 11 found 18 hours ago Roundtrip flight included Grand Rapids (GRR) to Springfield (VSF) 9.2/10 Wonderful! (117 reviews) Fantastic breakfast in this quaint inn. Right in the road so very easy to find. Wonderful meal in the attached restaurant. Friendly staff. Easy parking. Reviewed on Mar 29, 2026 ![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 $820 per person May 8 - May 11 found 18 hours ago Roundtrip flight included Grand Rapids (GRR) to Springfield (VSF) 8.6/10 Excellent! (847 reviews) No inflatable mattress offered anymore. Reviewed on Mar 18, 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 $870 per person May 8 - May 11 found 18 hours ago Roundtrip flight included Grand Rapids (GRR) 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 ![Solitude Village at Okemo by Vail Resorts](https://images.trvl-media.com/lodging/13000000/12530000/12521300/12521237/740d68de_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Solitude Village at Okemo by Vail Resorts Clock Tower Base Area $826 per person May 8 - May 11 found 18 hours ago Roundtrip flight included Grand Rapids (GRR) to Springfield (VSF) 7.8/10 Good! (35 reviews) Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also. Reviewed on Oct 8, 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=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 $130 nightly $143 total Apr 22 - Apr 23 Total with taxes and fees 7.4/10 Good! (1,002 reviews) was put in a room next to elevator, elevator was rubbing squeeling reported to front desk, they refused to move us, noise kept us up all night long. terrible experience. she said they didn't have any other rooms and refused to move us the hotel was clearly NOT full capacity. Elevator certificate ... Reviewed on Mar 31, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F22%2F2026&endDate=4%2F23%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 $131 nightly $144 total Apr 12 - Apr 13 Total with taxes and fees 7/10 Good! (1,000 reviews) Clean room and easy parking Reviewed on Mar 30, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%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 Apr 6 - Apr 7 Total with taxes and fees 9.4/10 Exceptional! (1,152 reviews) Clean room, friendly staff, good breakfast. Always enjoy staying at the Inn. 👍👍 Reviewed on Apr 5, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F6%2F2026&endDate=4%2F7%2F2026&selected=1108&PinnedHotelID=1108&HadPinnedHotel=true®ionId=7881) [See all 2,702 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=4%2F6%2F2026&endDate=4%2F7%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