Title: Windham County Vacations & Trips 2026 from CA $819 | Expedia.ca [Windham County Hotels](https://expedia.ca/Destinations-In-Windham-County.d6057353.Hotel-Destinations)[Vacation Rentals in Windham County](https://expedia.ca/Destinations-In-Windham-County.d6057353.Vacation-Rental-Destinations)[Windham County Car Rentals](https://expedia.ca/Destinations-In-Windham-County.d6057353.Car-Rental-Destinations) ![](https://images.trvl-media.com/place/6057353/bdb3e72e-fca5-4208-a6a4-c09318f6a7f8.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windham County Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Bruce Altobelli - ## 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 Windham County Vacation Answer the call of adventure with a tailor-made vacation package to Windham County. Wherever it is you're going and whatever you plan to do, prepare to discover a destination with plenty to offer. Kick off your trip to Windham County with a couple of nights in [Wilmington](https://www.expedia.ca/Wilmington.d175314.Destination-Travel-Guides) visiting popular attractions like Mount Snow and Mount Snow Golf Course. [Londonderry](https://www.expedia.ca/Londonderry.d127228.Destination-Travel-Guides) is another city that draws crowds from near and far. Magic Mountain Ski Resort and Jamaica State Park are two of the leading places to see in this destination. From the moment you book your Windham County vacation to when you get back home, Expedia has your back every step of the way. ## Top vacation destinations in Windham County ![](https://mediaim.expedia.com/destination/2/7293bdf66975e2ab77f3169d08030312.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Brattleboro [](https://expedia.ca/Brattleboro.d9636.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/dccef88d1434c06846bba7f35aaa8285.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Stratton [](https://expedia.ca/Stratton.d163002.Destination-Travel-Guides) ## Top Windham 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 $819 per person May 6 - May 10 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Springfield (VSF) 7.6/10 Good! (1,002 reviews) Easy check in and good parking Reviewed on Jan 9, 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 $994 per person May 6 - May 10 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) 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 $1,032 per person May 6 - May 10 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Rutland (RUT) 9/10 Wonderful! (1,000 reviews) The room was clean, staff was helpful and courteous, and the breakfast was excellent and so appreciated Reviewed on Feb 9, 2026 ![Latchis Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Latchis Hotel CA $1,005 per person May 6 - May 10 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Springfield (VSF) 8.4/10 Very Good! (822 reviews) Spotless room -- all the basics. Friendly & helpful staff Reviewed on Feb 1, 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_6057353) ## Windham County Hotel Deals ![The Black Bear Lodge at Stratton Mountain Resort](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/ac6aa3fb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Black Bear Lodge at Stratton Mountain Resort 5 Village Lodge Road Stratton VT CA $239 CA $290 total Mar 3 - Mar 4 includes taxes & fees 7.6/10 Good! (966 reviews) Accommodating staff Reviewed on Feb 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=03%2F03%2F2026&endDate=04%2F03%2F2026&selected=800765&PinnedHotelID=800765&HadPinnedHotel=true®ionId=6057353) ![Mount Snow Grand Summit Resort](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/57303655_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Mount Snow Grand Summit Resort 89 Grand Summit Way West Dover VT CA $431 CA $516 total Mar 16 - Mar 17 includes taxes & fees 8.6/10 Excellent! (254 reviews) Staff was great, location terrific, restaurant/bar very nice, room was really nice, kitchen well equipped Reviewed on Jan 19, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F03%2F2026&endDate=17%2F03%2F2026&selected=663170&PinnedHotelID=663170&HadPinnedHotel=true®ionId=6057353) ![Comfort Inn & Suites Brattleboro I-91](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites Brattleboro I-91 1186 Putney Road Brattleboro VT Fully refundableReserve now, pay when you stay CA $167 CA $184 total Mar 16 - Mar 17 includes taxes & fees 8.4/10 Very Good! (760 reviews) Nice location… clean room! Breakfast was not appetizing… Reviewed on Jan 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F03%2F2026&endDate=17%2F03%2F2026&selected=8784377&PinnedHotelID=8784377&HadPinnedHotel=true®ionId=6057353) [See all 1,409 properties in Windham County](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=14%2F02%2F2026&endDate=15%2F02%2F2026®ionId=6057353) 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 Windham County vacation package cost? ### How do I get a cheap travel package to Windham County? ### What are the top hotels in Windham County? ### How far in advance should I book my Windham County vacation? ### What does an Expedia Windham County travel package include? ### What should I know before booking a Windham County travel package? ### Can I choose my airline with a Windham County Expedia vacation package? ### If I'm not able to travel, can I cancel my Windham 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