Title: Cherry Plain Vacation Packages & Trips 2026 | Expedia.ca [Hotels in Cherry Plain](https://expedia.ca/Cherry-Plain-Hotels.d553248635975873940.Travel-Guide-Hotels)[Vacation Rentals in Cherry Plain](https://expedia.ca/Cherry-Plain-Vacation-Rentals.d553248635975873940.Travel-Guide-VacationRentals)[Cherry Plain Car Rentals](https://expedia.ca/Car-Rentals-In-Cherry-Plain.d553248635975873940.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Cherry Plain Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## 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 ![](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_553248635975873940) ## Ready to book your vacation to Cherry Plain? Choose your dates ## Cherry Plain Hotel Deals ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Vacation Village in the Berkshires 276 Brodie Mountain Rd Williamstown MA Fully refundableReserve now, pay when you stay CA $142 CA $174 total Feb 23 - Feb 24 includes taxes & fees 8.8/10 Excellent! (2,257 reviews) The staff was wonderful and the pool was great. Reviewed on Feb 21, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&selected=1066423&PinnedHotelID=1066423&HadPinnedHotel=true®ionId=553248635975873940) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshire Mountain Lodge 8 Dan Fox Dr Pittsfield MA Fully refundableReserve now, pay when you stay CA $137 CA $183 total Mar 23 - Mar 24 includes taxes & fees 9/10 Wonderful! (852 reviews) The staff were friendly and welcoming and the rooms were spacious and clean. Pool and hot tub were fun after a long day of skiing. It was an overall great experience. The hot cocoa and coffee was a nice touch and would recommend this hotel to any skiers or snowboarders trying out the nearby ... Reviewed on Feb 21, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F03%2F2026&endDate=24%2F03%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=553248635975873940) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Williams Inn 101 Spring Street Williamstown MA Fully refundableReserve now, pay when you stay CA $257 CA $287 total Feb 23 - Feb 24 includes taxes & fees 9.6/10 Exceptional! (577 reviews) Elegant and oupdated decor throughout, spotlessly clean Welocation, Reviewed on Feb 21, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&selected=35658765&PinnedHotelID=35658765&HadPinnedHotel=true®ionId=553248635975873940) [See all 657 properties in Cherry Plain](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=23%2F02%2F2026&endDate=24%2F02%2F2026®ionId=553248635975873940) 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) ## Explore a world of travel with Expedia \* 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