Title: Pittsfield Vacation Packages & Trips 2026 from CA $1,179 | Expedia.ca [Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d9478.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d9478.Travel-Guide-VacationRentals)[Flights to Pittsfield](https://expedia.ca/Cheap-Flights-To-Pittsfield.d9478.Travel-Guide-Flights)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d9478.Car-Rental-Guide) ![](https://images.trvl-media.com/place/9478/5d9f4527-2b11-4f19-a1cd-36a7128d1304.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Pittsfield 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 Pittsfield Vacation When you book a Pittsfield vacation package, you can kick back and enjoy your escape to the fullest. Delve into the highlights of this exciting city knowing that all your travel arrangements have been looked after before you go. A trip to Pittsfield is a wonderful opportunity to sightsee. Be sure to stop by big-name attractions such as [Bousquet Ski Area](https://www.expedia.ca/Bousquet-Ski-Area-Pittsfield.d553248621532665283.Vacation-Attraction), [Colonial Theater](https://www.expedia.ca/Colonial-Theater-Pittsfield.d553248621532665289.Vacation-Attraction) and [Hancock Shaker Village](https://www.expedia.ca/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction). Expedia will help you escape the everyday. Tailor your vacation to Pittsfield to suit your style of travel, whatever that may look like. ## Top Pittsfield Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Lake Haven Motel](https://images.trvl-media.com/lodging/20000000/19300000/19294100/19294012/b9bd3874_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lake Haven Motel CA $1,179 per person May 15 - May 17 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Albany (ALB) 7.4/10 Good! (110 reviews) Newly renovated while still keeping the “lake camp” charm. Great little efficiency- spotless Reviewed on Nov 29, 2025 ![The Manchester View](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/738a0d56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Manchester View CA $1,254 per person May 22 - May 25 found 16 hours ago Roundtrip non-stop flight included Calgary (YYC) to Albany (ALB) 9.4/10 Exceptional! (818 reviews) Beautiful property, clean room, friendly staff. Will definitely be staying here again! Reviewed on Mar 18, 2026 ![Hotel Brookmere & Arbor Spa](https://images.trvl-media.com/lodging/107000000/106890000/106887400/106887312/6379fb71_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Brookmere & Arbor Spa CA $1,231 per person May 15 - May 17 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Albany (ALB) 9.2/10 Wonderful! (271 reviews) Located by the elevator was a bit noisy. Other than that, wonderful stay! Reviewed on Mar 11, 2026 ![Hilton Garden Inn Saratoga Springs](https://images.trvl-media.com/lodging/1000000/300000/296600/296564/356364a8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Saratoga Springs CA $1,268 per person May 15 - May 17 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Albany (ALB) 8/10 Very Good! (1,005 reviews) Clean room and friendly staff Reviewed on Mar 16, 2026 ![Sundowner on Lake George](https://images.trvl-media.com/lodging/2000000/1240000/1235000/1234914/76661ecf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sundowner on Lake George CA $1,193 per person May 15 - May 17 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Albany (ALB) 7.6/10 Good! (247 reviews) The place was nice and clean with plenty of room for 2 couples Reviewed on Mar 1, 2026 ## Ready to book your vacation to Pittsfield? Choose your dates ## Pittsfield Hotel Deals ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_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 $120 CA $165 total Apr 26 - Apr 27 includes taxes & fees 9/10 Wonderful! (888 reviews) very clean and friendly staff Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F04%2F2026&endDate=27%2F04%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=9478) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG One West Street Pittsfield MA Fully refundable CA $178 CA $199 total Mar 30 - Mar 31 includes taxes & fees 8/10 Very Good! (1,000 reviews) Staff was pleasant! Clean and the restaurant was excellent! Reviewed on Mar 22, 2026 [](https://expedia.ca/Hotel-Search?startDate=30%2F03%2F2026&endDate=31%2F03%2F2026&selected=2067&PinnedHotelID=2067&HadPinnedHotel=true®ionId=9478) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/ef3ce5c5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel On North 297 North Street Pittsfield MA Fully refundableReserve now, pay when you stay CA $206 CA $231 total Mar 30 - Mar 31 includes taxes & fees 9.6/10 Exceptional! (837 reviews) The hotel was even more beautiful in person! Rooms were incredibly spacious and lovely. The staff was incredibly friendly and helpful. Great stay would definitley return. Reviewed on Mar 16, 2026 [](https://expedia.ca/Hotel-Search?startDate=30%2F03%2F2026&endDate=31%2F03%2F2026&selected=10246103&PinnedHotelID=10246103&HadPinnedHotel=true®ionId=9478) [See all 1,366 properties in Pittsfield](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=28%2F03%2F2026&endDate=29%2F03%2F2026®ionId=9478) 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) ### Discover the most popular places to visit in Pittsfield ![Hancock Shaker Village](https://images.trvl-media.com/place/112303/51d1465f-7568-4ca1-ab97-760ab0d2a7f2.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Hancock Shaker Village You can browse the exhibits at Hancock Shaker Village, a museum with a storied past, during your trip to Pittsfield. Wander the lakeside in this quaint area. [](https://expedia.ca/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction) #### Canoe Meadows Wildlife Sanctuary You can take time to visit Canoe Meadows Wildlife Sanctuary during your travels to Pittsfield. Wander the lakeside in this family-friendly area. [](https://expedia.ca/Canoe-Meadows-Wildlife-Sanctuary-Pittsfield.d553248621532665285.Vacation-Attraction) ## 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