Title: Windsor Vacation Packages & Trips 2026 | Expedia.ca [Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d7881.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d7881.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.ca/Cheap-Flights-To-Windsor.d7881.Travel-Guide-Flights)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d7881.Car-Rental-Guide) ![](https://images.trvl-media.com/place/7881/9675231b-9d1e-4af8-9ac0-4a4684345ff1.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windsor Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by mike dobias - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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.ca/Mount-Ascutney-Windsor.d553248621532666931.Vacation-Attraction), [Blow-Me-Down Bridge](https://www.expedia.ca/Blow-Me-Down-Bridge-Cornish.d553248621532666969.Vacation-Attraction) and [Mt Ascutney State Park](https://www.expedia.ca/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. ### Things to do in and around Windsor Windsor, Vermont, is an ideal destination for adventure enthusiasts and outdoor lovers. With its renowned ski resorts and fields, visitors can enjoy thrilling winter sports. Additionally, Windsor offers family outings and is perfect for a relaxing beach vacation. Whether you're seeking an exhilarating break or a peaceful escape, Windsor has something for everyone to enjoy in the great outdoors. **Shopping** In Windsor, visit [The Sustainable Farmer](https://www.expedia.ca/The-Sustainable-Farmer.d553248621532666964.Vacation-Attraction) for unique gifts. For a bit of a drive, head to [Quechee Gorge Village](https://www.expedia.ca/Quechee-Gorge-Village.d6175190.Vacation-Attraction), 17.7km away, for charming shops and souvenirs. Closer by, [North Country Smokehouse](https://www.expedia.ca/North-Country-Smokehouse.d553248621532666957.Vacation-Attraction), just 11.3km from Windsor, offers local delicacies perfect for gifts. **Recreation** The [Upper Valley Aquatic Center](https://www.expedia.ca/Upper-Valley-Aquatic-Center.d6329639.Vacation-Attraction), located 17.7km from Windsor, offers a family-friendly atmosphere with a variety of aquatic activities. Nearby, the [Woodstock Town Hall Theatre](https://www.expedia.ca/Woodstock-Town-Hall-Theatre.d6329612.Vacation-Attraction) presents cultural and romantic performances, while the [Woodstock Country Club](https://www.expedia.ca/Woodstock-Country-Club.d6329607.Vacation-Attraction) provides a scenic golf course for outdoor sports enthusiasts. **Adventure** Explore the scenic [Brownsville Trail](https://www.expedia.ca/Brownsville-Trail.d553248621532666963.Vacation-Attraction) for a refreshing outdoor experience in Windsor. Enjoy skiing and snowboarding at [Arrowhead Recreation Area](https://www.expedia.ca/Arrowhead-Recreation-Area.d6110774.Vacation-Attraction), located 14.5km from Windsor, or unleash your competitive spirit at [Maple Lanes](https://www.expedia.ca/Maple-Lanes.d553248621532666956.Vacation-Attraction), an exciting arcade adventure zone situated 12.9km away, perfect for family fun. **Nightlife** Windsor offers a charming nightlife with cozy pubs and local eateries. Visit the Harpoon Brewery for craft beers and tasty bites, then head to the Windsor Station for live music and a vibrant atmosphere. Enjoy the friendly vibe and meet locals while soaking in the evening's excitement. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Find the best attractions near Windsor Windsor, Vermont, is an ideal destination for adventure seekers and outdoor enthusiasts, offering a blend of historic sites, national parks, and environmental centres. Visitors can enjoy cultural experiences and family-friendly activities, while also exploring local attractions such as vacation rental resorts and seasonal festivals. Don't miss the chance to experience the charm of nearby landmarks, including Windsor Island and the renowned Windsor Castle, making it a perfect getaway for all types of travellers. - **[Blow-Me-Down Bridge: ](https://www.expedia.ca/Blow-Me-Down-Bridge.d553248621532666969.Vacation-Attraction)** This historic bridge, located 805m from Windsor, offers a charming glimpse into the area’s rich cultural heritage. Its picturesque setting and unique architecture make it a perfect spot for photography and leisurely walks, allowing visitors to appreciate the local history. - **[Mount Ascutney: ](https://www.expedia.ca/Mount-Ascutney.d553248621532666931.Vacation-Attraction)** Just 6.4km away, Mount Ascutney is a haven for outdoor enthusiasts. With breathtaking scenery, hiking trails, and opportunities for adventure sports, this mountain provides a thrilling escape into nature, ideal for both seasoned adventurers and casual hikers. - **[Saint-Gaudens National Historic Site: ](https://www.expedia.ca/Saint-Gaudens-National-Historic-Site.d6110820.Vacation-Attraction)** Located 3.2km from Windsor, this historic site celebrates the life and work of renowned sculptor Augustus Saint-Gaudens. Visitors can explore stunning sculptures and beautiful gardens, immersing themselves in the artistry and culture of the period. ### Best time to go to Windsor The best time to visit Windsor can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windsor falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Windsor falls in January, visitor numbers are average and weather is mostly with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 16.7°F (-8.5°C) | Light Rain | Mostly | Average | Average | | February | 18.9°F (-7.3°C) | Light Rain | Mostly | Slightly Low | Slightly High | | March | 27.1°F (-2.7°C) | Light Rain | Mostly | Average | Average | | April | 39.4°F (4.1°C) | Light Rain | Mostly | Average | Slightly Low | | May | 52.3°F (11.3°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | June | 59.9°F (15.5°C) | Light Rain | Mostly Sunny | Average | Average | | July | 65.8°F (18.8°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 64.0°F (17.8°C) | Light Rain | Mostly Sunny | Slightly High | Average | | September | 57.0°F (13.9°C) | Light Rain | Mostly Sunny | Slightly High | Average | | October | 45.5°F (7.5°C) | Light Rain | Mostly | Average | Slightly High | | November | 33.1°F (0.6°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | December | 24.3°F (-4.3°C) | Light Rain | Mostly | Slightly Low | Slightly High | ### Tips to save on your trip to Windsor - Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Windsor. - Consider traveling to Windsor during the low season (April to May and November) for more affordable options. - Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget. - Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties. ## Ready to book your vacation to Windsor? Choose your dates ## Windsor Hotel Deals ![White River Inn and Suites](https://images.trvl-media.com/lodging/1000000/30000/28000/27933/f779e2ff_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 6.8/10 (1,004 reviews) Very nice hotel, location was perfect. Reviewed on Dec 20, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=07%2F01%2F2026&endDate=08%2F01%2F2026&selected=27933&PinnedHotelID=27933&HadPinnedHotel=true®ionId=7881) [](https://expedia.ca/Hotel-Search?startDate=07%2F01%2F2026&endDate=08%2F01%2F2026&selected=27933&PinnedHotelID=27933&HadPinnedHotel=true®ionId=7881) ![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 CA $266 CA $293 total Jan 21 - Jan 22, 2026 includes taxes & fees 7.2/10 Good! (1,002 reviews) Very happy. Reviewed on Dec 19, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F01%2F2026&endDate=22%2F01%2F2026&selected=103640&PinnedHotelID=103640&HadPinnedHotel=true®ionId=7881) ![The Mountain Inn at Killington](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Mountain Inn at Killington 47 Old Mill Rd Killington VT 9/10 Wonderful! (966 reviews) Great inn!!! Close to everything and specially the mountain Reviewed on Dec 17, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=07%2F01%2F2026&endDate=08%2F01%2F2026&selected=975389&PinnedHotelID=975389&HadPinnedHotel=true®ionId=7881) [](https://expedia.ca/Hotel-Search?startDate=07%2F01%2F2026&endDate=08%2F01%2F2026&selected=975389&PinnedHotelID=975389&HadPinnedHotel=true®ionId=7881) [See all 2,625 properties in Windsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F12%2F2025&endDate=26%2F12%2F2025®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. ![](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.ca/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.ca/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) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in Windsor #### The Sustainable Farmer Enjoy an outing to The Sustainable Farmer during your stay in Windsor. Wander the riverfront in this quaint area. 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