Title: Windsor County Vacations & Trips 2026 from CA $629 | Expedia.ca [Windsor County Hotels](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Hotel-Destinations)[Vacation Rentals in Windsor County](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Vacation-Rental-Destinations)[Windsor County Car Rentals](https://expedia.ca/Destinations-In-Windsor-County.d553248635976432508.Car-Rental-Destinations) ![](https://images.trvl-media.com/place/3000459649/7d354301-07a8-4d26-bfd8-54320ed05c30.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windsor County Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Rachel Samanyi - ## 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 County Vacation With a Windsor County vacation package, you can forget about planning hassles and instead focus on experiencing everything this exciting destination has on offer. Begin your trip to Windsor County with some time exploring [Ludlow](https://www.expedia.ca/Ludlow.d8496.Destination-Travel-Guides) visiting popular sights like Weston Playhouse and Lake Rescue. [Norwich](https://www.expedia.ca/Norwich.d184063.Destination-Travel-Guides) is another top city that lures crowds from near and far. Quechee Gorge Bridge and Quechee Gorge Village are two of the leading places to see in this destination. From the instant you book your Windsor County vacation to the second you come back home, Expedia will take care of you each step of the way. ## Top vacation destinations in Windsor County ![Ludlow showing street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94298-Ludlow.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Ludlow [](https://expedia.ca/Ludlow.d8496.Destination-Travel-Guides) ![Woodstock featuring a house](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/94000/94311-Woodstock.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Woodstock [](https://expedia.ca/Woodstock.d10868.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/212ecbf3b606238229538e223f3f57eb.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### White River Junction [](https://expedia.ca/White-River-Junction.d6294.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/e6f5a135e5990faead3b19a2481c6d2b.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Windsor [](https://expedia.ca/Windsor.d7881.Destination-Travel-Guides) ## Top Windsor County Vacation Deals 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 CA $629 per person Apr 26 - Apr 29 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to Springfield (VSF) 7.6/10 Good! (1,002 reviews) Room worn. Dirty parking lot. Worn rugs in room. Noisy room at night, had to call desk for 3 am noise. Found out homeless were sheltered there from folk at next door McDonalds. Desk did not know where the Motel was located on the tourist supplied in lobby. Prices dropped $38.00 online after we booked. Ted Koczynski. Reviewed on Feb 18, 2026 ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shire Woodstock CA $732 per person Apr 26 - Apr 29 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to Springfield (VSF) 8.8/10 Excellent! (881 reviews) Woodstock is a magical place! We love staying at the Shire! They really make it feel like home! So cozy! The staff is very friendly and accommodating! We will always stay at the Shire! Reviewed on Jan 30, 2026 ![Holiday Inn Club Vacations Mount Ascutney Resort by IHG](https://images.trvl-media.com/lodging/1000000/430000/425200/425171/fead325a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Club Vacations Mount Ascutney Resort by IHG CA $677 per person Apr 26 - Apr 29 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to Lebanon (LEB) 9/10 Wonderful! (774 reviews) The room was clean but the plumbing in the bathrooms is so outdated and needs replacement. We love staying at this place and this was our first time at Bennington. It looks upgraded compared to Hanover and was really well done. Reviewed on Feb 19, 2026 ![Mount Snow Grand Summit Resort](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/57303655_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Mount Snow Grand Summit Resort CA $743 per person Apr 26 - Apr 29 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to Springfield (VSF) 8.8/10 Excellent! (242 reviews) Staff was great, location terrific, restaurant/bar very nice, room was really nice, kitchen well equipped Reviewed on Jan 19, 2026 ![The Quechee Inn at Marshland Farm](https://images.trvl-media.com/lodging/2000000/1930000/1924800/1924710/c8372335_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Quechee Inn at Marshland Farm CA $771 per person Apr 26 - Apr 29 found 1 day ago Roundtrip non-stop flight included Winnipeg (YWG) to Rutland (RUT) 9/10 Wonderful! (1,000 reviews) This was our third trip to the hotel and we love it evetytime we stay there. Reviewed on Feb 15, 2026 ![](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.ca/deals?rfrr=PKG_SPRING_PROMO_553248635976432508) ## Windsor County Hotel Deals ![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 Fully refundableReserve now, pay when you stay CA $148 CA $163 total Feb 22 - Feb 23 includes taxes & fees 9.4/10 Exceptional! (1,117 reviews) Very clean, pleasant staff, recommend. Reviewed on Feb 20, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=1108&PinnedHotelID=1108&HadPinnedHotel=true®ionId=553248635976432508) ![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 CA $192 CA $219 total Mar 4 - Mar 5 includes taxes & fees 8.8/10 Excellent! (984 reviews) We stayed one night in room 107\. It was roomier than many other hotels these days and had a comfortable bed. We were pleasantly surprised to have a mini fridge that actually worked. Furniture is a bit worn and the carpet has some mileage on it. Bathroom was clean and shower worked well. The hot tub ... Reviewed on Feb 17, 2026 [](https://expedia.ca/Hotel-Search?startDate=04%2F03%2F2026&endDate=05%2F03%2F2026&selected=1823093&PinnedHotelID=1823093&HadPinnedHotel=true®ionId=553248635976432508) ![Woodstock Inn & Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Woodstock Inn & Resort Fourteen The Green Woodstock VT CA $409 CA $510 total Feb 22 - Feb 23 includes taxes & fees 9.2/10 Wonderful! (564 reviews) Incredible experience. Can’t wait to return Reviewed on Feb 13, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=25690&PinnedHotelID=25690&HadPinnedHotel=true®ionId=553248635976432508) [See all 1,361 properties in Windsor County](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=21%2F02%2F2026&endDate=22%2F02%2F2026®ionId=553248635976432508) 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) ## Frequently asked questions ### How much does a Windsor County vacation package cost? ### How do I get a cheap travel package to Windsor County? ### Where should I stay in Windsor County? ### What are the top hotels in Windsor County? ### How far in advance should I book my Windsor County vacation? ### What does an Expedia Windsor County travel package include? ### What should I know before booking a Windsor County travel package? ### Can I choose my airline with a Windsor County Expedia vacation package? ### If I'm not able to travel, can I cancel my Windsor County vacation package? \* 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 on select hotels and earn double points 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