Title: Windham County Vacations & Trips 2026 from CA $1,086 | 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 ![Autumn colors along Connecticut River, Brattleboro, Vermont](https://images.trvl-media.com/place/9636/028a402e-1933-4649-ba79-261aea048ad3.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Brattleboro [](https://expedia.ca/Brattleboro.d9636.Destination-Travel-Guides) ![Autumn at Jones Pond - Carrabassett Valley - Maine - Bigelow Preserve Peak](https://images.trvl-media.com/place/163002/2c2fe06f-9c24-49c7-abde-ddaf8f23f7c4.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. ![Hideaway Inn Mt. Snow](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/c5bdc83b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hideaway Inn Mt. Snow CA $1,086 per person May 13 - May 16 found 20 hours ago Roundtrip flight included Edmonton (YEG) to Springfield (VSF) 8.8/10 Excellent! (69 reviews) I loved staying here and can’t wait to do so again. The room was clean, cozy and comfortable. Loved the automated check in with clear directions. The entire place was decked out with awesome ambience and decor. I just wish the hot tub was working. It’s so close to Mount Snow too! Reviewed on Mar 18, 2026 ![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 CA $1,155 per person May 13 - May 16 found 20 hours ago Roundtrip flight included Edmonton (YEG) to Springfield (VSF) 9.4/10 Exceptional! (113 reviews) Only issue is there was nowhere to hang anything and the room was very small. Room was clean, comfortable and bathroom was well-appointed. Breakfast was good and staff friendly and helpful. Close to restaurants and super easy access to Mt. Snow. Would definitely stay here again. Reviewed on Mar 28, 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 CA $1,273 per person May 13 - May 16 found 20 hours ago Roundtrip flight included Edmonton (YEG) 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 ![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 CA $1,236 per person May 13 - May 16 found 20 hours ago Roundtrip flight included Edmonton (YEG) to Springfield (VSF) 8.6/10 Excellent! (847 reviews) No inflatable mattress offered anymore. Reviewed on Mar 18, 2026 ![Okemo Mountain Lodging by Vail Resorts](https://images.trvl-media.com/lodging/33000000/32350000/32342000/32341945/05713f89_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Okemo Mountain Lodging by Vail Resorts Clock Tower Base Area CA $1,346 per person May 13 - May 16 found 20 hours ago Roundtrip flight included Edmonton (YEG) to Springfield (VSF) 7.8/10 Good! (28 reviews) Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June. Reviewed on Jun 26, 2025 ## Windham County Hotel Deals ![Hideaway Inn Mt. Snow](https://images.trvl-media.com/lodging/123000000/122980000/122978200/122978111/c5bdc83b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hideaway Inn Mt. Snow 270 Handle Rd West Dover VT Fully refundableReserve now, pay when you stay CA $136 CA $150 total Apr 14 - Apr 15 includes taxes & fees 8.6/10 Excellent! (80 reviews) The bath soap container was empty. I asked a hotel staff member if she could refill the dispenser and she said she would bring it to my room in a few minutes. She never showed up as promised. I passed her on the way out 45 minutes later. She look at me and went on her business. Reviewed on Mar 22, 2026 [](https://expedia.ca/Hotel-Search?startDate=14%2F04%2F2026&endDate=15%2F04%2F2026&selected=122978111&PinnedHotelID=122978111&HadPinnedHotel=true®ionId=6057353) ![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/05f7e3bc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Colonial Motel And Spa 889 Putney Rd Brattleboro VT Fully refundableReserve now, pay when you stay CA $132 CA $145 total Apr 2 - Apr 3 includes taxes & fees 6.8/10 (1,000 reviews) Plenty of parking Clean - no bugs Goes downhill from there. Front desk people were polite but far from friendly. Major renovations need to be done before I will come back. Windows did not lock, which my husband discovered as we were getting ready for bed. He decided that they were too small for anyone ... Reviewed on Mar 30, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F04%2F2026&endDate=03%2F04%2F2026&selected=1070729&PinnedHotelID=1070729&HadPinnedHotel=true®ionId=6057353) ![Grand Summit Resort, A Vail Resorts Property](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/7d1f7aea_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Grand Summit Resort, A Vail Resorts Property 89 Grand Summit Way West Dover VT Fully refundable CA $215 CA $257 total Apr 20 - Apr 21 includes taxes & fees 8.6/10 Excellent! (266 reviews) Room was on the small side and it's usually standard that the room have a pull our sofa bed but ours did not. Rooms had a small full kitchen which is really great. The location was amazing, right on the mountain and everything you need to ski is right there. It's also nice to be able to stroll to ... Reviewed on Mar 19, 2026 [](https://expedia.ca/Hotel-Search?startDate=20%2F04%2F2026&endDate=21%2F04%2F2026&selected=663170&PinnedHotelID=663170&HadPinnedHotel=true®ionId=6057353) [See all 1,414 properties in Windham County](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=02%2F04%2F2026&endDate=03%2F04%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