Title: Pittsfield Vacation Packages & Trips 2026 from CA $924 | Expedia.ca [Pittsfield Travel Guide](https://expedia.ca/Pittsfield.dx184066)[Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d184066.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d184066.Travel-Guide-VacationRentals)[Flights to Pittsfield](https://expedia.ca/Cheap-Flights-To-Pittsfield.d184066.Travel-Guide-Flights)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d184066.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) # 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 Get ready to experience Pittsfield in your own style with a custom Pittsfield vacation package! Uncovering the charms of this captivating city is made easier with a base in a neighborhood such as West Bridgewater, which is good for skiing, among many other things. [Appalachian Trail Adventures](https://www.expedia.ca/Appalachian-Trail-Adventures-Rutland.d553248621532667612.Vacation-Attraction), [Green Mountain National Golf Course](https://www.expedia.ca/Green-Mountain-National-Golf-Course-Killington.d6115884.Vacation-Attraction) and [Lefferts Pond](https://www.expedia.ca/Lefferts-Pond-Chittenden.d6291323.Vacation-Attraction) are just some of the many sights you'll want to see during your trip to Pittsfield. A couple of quick clicks is all it takes to put together your perfect Pittsfield vacation on Expedia. ## Top Pittsfield Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Align Inn Vermont](https://images.trvl-media.com/lodging/1000000/10000/1200/1108/996cad8e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Align Inn Vermont CA $924 per person Apr 24 - Apr 26 found 17 hours ago Roundtrip non-stop flight included Montreal (YMQ) to Rutland (RUT) 9.4/10 Exceptional! (1,017 reviews) Very clean room, kind staff and excellent breakfast. Reviewed on Feb 6, 2026 ![The Quechee Inn at Marshland Farm](https://images.trvl-media.com/lodging/2000000/1930000/1924800/1924710/c8372335_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Quechee Inn at Marshland Farm CA $979 per person Apr 24 - Apr 26 found 17 hours ago Roundtrip non-stop flight included Montreal (YMQ) to Rutland (RUT) 9/10 Wonderful! (1,000 reviews) The room was clean, staff was helpful and courteous, and the breakfast was excellent and so appreciated Reviewed on Feb 9, 2026 ![Lake Bomoseen Lodge](https://images.trvl-media.com/lodging/22000000/21230000/21223500/21223495/e1cbb293_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lake Bomoseen Lodge CA $981 per person Apr 24 - Apr 26 found 17 hours ago Roundtrip non-stop flight included Montreal (YMQ) to Rutland (RUT) 9.4/10 Exceptional! (851 reviews) Room was clean, comfortable and had a beautiful view of the lake. Staff was very friendly. Only complaint is that the floor of the room was very cold. Reviewed on Jan 29, 2026 ![North Star Lodge and Resort](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/0612ebf1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### North Star Lodge and Resort CA $946 per person Apr 24 - Apr 26 found 17 hours ago Roundtrip non-stop flight included Montreal (YMQ) to Rutland (RUT) 8.6/10 Excellent! (1,001 reviews) Great place! Everything you need for affordable ski lodging. Reviewed on Feb 12, 2026 ![Emrose Luxury Cabins](https://images.trvl-media.com/lodging/111000000/110250000/110247200/110247154/fb359a4e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Emrose Luxury Cabins CA $998 per person Apr 24 - Apr 26 found 17 hours ago Roundtrip non-stop flight included Montreal (YMQ) to Rutland (RUT) 9/10 Wonderful! (65 reviews) Lovely place. Comfortable. Reviewed on Feb 9, 2026 ![](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_184066) ## Ready to book your vacation to Pittsfield? Choose your dates ## Pittsfield Hotel Deals ![Killington Mountain Lodge, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/403a8548_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Killington Mountain Lodge, Tapestry Collection by Hilton 2617 Killington Rd Killington VT Fully refundableReserve now, pay when you stay CA $212 CA $233 total Mar 1 - Mar 2 includes taxes & fees 7.2/10 Good! (1,000 reviews) Close to the resort, nice hot tub, decent room with a modern tv software for easy connections. Good price to hotel quality ratio. Reviewed on Jan 26, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=103640&PinnedHotelID=103640&HadPinnedHotel=true®ionId=184066) ![Best Western Inn & Suites Rutland-Killington](https://images.trvl-media.com/lodging/1000000/20000/16500/16411/9898f616_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Inn & Suites Rutland-Killington 5 Best Western Place Rutland VT Fully refundableReserve now, pay when you stay CA $178 CA $196 total Mar 2 - Mar 3 includes taxes & fees 8.6/10 Excellent! (999 reviews) Staff was very attentive and helpful, rooms very clean and comfortable with well organized setting, breakfast was pretty good and it is included with your stay. Reviewed on Feb 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=02%2F03%2F2026&endDate=03%2F03%2F2026&selected=16411&PinnedHotelID=16411&HadPinnedHotel=true®ionId=184066) ![Comfort Inn Rutland - Killington](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/15d4fef0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn Rutland - Killington 19 Allen St Rutland VT Fully refundableReserve now, pay when you stay CA $195 CA $214 total Mar 15 - Mar 16 includes taxes & fees 8/10 Very Good! (1,004 reviews) Everything was great! The staff were very nice and the free breakfast is legit! Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F03%2F2026&endDate=16%2F03%2F2026&selected=4621&PinnedHotelID=4621&HadPinnedHotel=true®ionId=184066) [See all 1,833 properties in Pittsfield](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=13%2F02%2F2026&endDate=14%2F02%2F2026®ionId=184066) 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