Title: Cummington Vacation Packages & Trips 2026 from CA $965 | 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. ![Global Luxury Suites East Boston](https://images.trvl-media.com/lodging/60000000/59300000/59296500/59296491/a5dc30b0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Global Luxury Suites East Boston East Boston CA $965 per person Apr 30 - May 4 found 11 hours ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 6.8/10 (173 reviews) The room is clean and the furniture is pretty, but since it's part of an apartment complex, you don't have immediate help with extra sheets or heater support; so first two days out 4, we had to deal with the cold of the room. Third and 4th, since we had called for help, they did left the extra sheets and fixed the thermostat. Reviewed on Dec 6, 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 $1,643 per person Apr 29 - May 2 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 ![Mandarin Oriental, Boston](https://images.trvl-media.com/lodging/3000000/2180000/2175200/2175117/be69f75d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Mandarin Oriental, Boston Back Bay CA $3,272 per person Mar 30 - Apr 5 found 8 hours ago Roundtrip non-stop flight included Winnipeg (YWG) to Boston (BOS) 9.4/10 Exceptional! (376 reviews) The rooms are spotless , staff are extremely welcoming. Everything and more you could want while staying in Boston Reviewed on Feb 8, 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 10 - Feb 11 includes taxes & fees 8.6/10 Excellent! (2,227 reviews) Spacious 2 bed 2 bath! Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=10%2F02%2F2026&endDate=11%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 10 - Feb 11 includes taxes & fees 9.2/10 Wonderful! (2,238 reviews) Clean, safe, quiet, and comfortable. Fantastic full breakfast as always. Reviewed on Feb 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=10%2F02%2F2026&endDate=11%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 10 - Feb 11 includes taxes & fees 9/10 Wonderful! (830 reviews) The doors wouldn’t stay locked Reviewed on Feb 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=10%2F02%2F2026&endDate=11%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=10%2F02%2F2026&endDate=11%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