Title: Cummington Vacation Packages & Trips 2026 from CA $1,069 | Expedia.ca [Hotels in Cummington](https://expedia.ca/Cummington-Hotels.d183324.Travel-Guide-Hotels)[Vacation Rentals in Cummington](https://expedia.ca/Cummington-Vacation-Rentals.d183324.Travel-Guide-VacationRentals)[Cummington Car Rentals](https://expedia.ca/Car-Rentals-In-Cummington.d183324.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) # Cummington 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 #### Your Cummington Vacation Take the stress out of planning your next epic adventure with a Cummington vacation package. Whether you're visiting for its food, history, art or other highlights, there's a never-ending supply of new experiences to be had. If seeing the sights is a priority during your trip to Cummington, make sure you stop by leading attractions like [Chesterfield Gorge](https://www.expedia.ca/Chesterfield-Gorge-Chesterfield.d553248621532666609.Vacation-Attraction) and [Swift River](https://www.expedia.ca/Swift-River-Massachusetts.d681613380051832832.Vacation-Attraction). Browse Expedia's wide range of travel options and start organizing your dream vacation to Cummington now. ## Top Cummington Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Maverick Suites at 245 Newbury St](https://images.trvl-media.com/lodging/90000000/89760000/89756300/89756238/2e7614de_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Maverick Suites at 245 Newbury St Back Bay CA $1,069 per person Mar 18 - Mar 24 found 2 hours ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 8.2/10 Very Good! (151 reviews) Room was clean and a good size. Location was perfect - walking distance to where I needed to be. Reviewed on Dec 2, 2025 ![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boston Harbor Hotel North End CA $1,490 per person Apr 3 - Apr 6 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.8/10 Exceptional! (1,005 reviews) Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem. Reviewed on Jan 25, 2026 ![The Charles Hotel](https://images.trvl-media.com/lodging/1000000/20000/15900/15861/66098bc6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Charles Hotel West Cambridge CA $1,566 per person Mar 12 - Mar 16 found 1 day ago Roundtrip flight included Halifax (YHZ) to Boston (BOS) 9.4/10 Exceptional! (1,003 reviews) Room very well appointed and gym was the stand out Reviewed on Jan 25, 2026 ![Raffles Boston](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/0f66f064_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Raffles Boston Back Bay CA $2,384 per person Apr 23 - Apr 26 found 1 day ago Roundtrip flight included Halifax (YHZ) to Boston (BOS) 9.6/10 Exceptional! (181 reviews) Everything was great — room was immaculate, hotel was very nice. Would return! Reviewed on Feb 1, 2026 ## Ready to book your vacation to Cummington? Choose your dates ## Cummington 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 8 - Feb 9 includes taxes & fees 8.6/10 Excellent! (2,221 reviews) Everything was great, the staff, the room, and the amenities. We will be coming back. Reviewed on Jan 25, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=1066423&PinnedHotelID=1066423&HadPinnedHotel=true®ionId=183324) ![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### D. Hotel Suites & Spa 1 Country Club Rd Holyoke MA Fully refundableReserve now, pay when you stay CA $141 CA $164 total Feb 8 - Feb 9 includes taxes & fees 9.2/10 Wonderful! (2,231 reviews) Clean, cozy on a very cold night! Breakfast had a good variety and staff was pleasant. Will definitely go back Reviewed on Jan 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=849303&PinnedHotelID=849303&HadPinnedHotel=true®ionId=183324) ![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 $135 CA $181 total Feb 8 - Feb 9 includes taxes & fees 9/10 Wonderful! (825 reviews) We had a lovely extended family weekend here. The staff was outstanding, every staff member was helpful, friendly and courteous. The large room in back of the lobby was especially helpful for our large group to hang out in and be comfortable. Everyone enjoyed the pool and hot tub despite it being ... Reviewed on Feb 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=183324) [See all 913 properties in Cummington](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026®ionId=183324) 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