Title: Pittsfield Vacation Packages & Trips 2026 from CA $939 | 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. ![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 $939 per person Mar 19 - Mar 22 found 13 hours ago Roundtrip non-stop flight included Toronto (YTO) 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 ![The Mountain Top Inn & Resort](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/53dd6cd4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Mountain Top Inn & Resort CA $1,226 per person Mar 19 - Mar 22 found 13 hours ago Roundtrip non-stop flight included Toronto (YTO) to Rutland (RUT) 9/10 Wonderful! (93 reviews) Location is excellent. Room is dated. Reviewed on Jan 26, 2026 ![Killington Mountain Lodge, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/403a8548_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Killington Mountain Lodge, Tapestry Collection by Hilton CA $1,216 per person Mar 19 - Mar 22 found 13 hours ago Roundtrip non-stop flight included Toronto (YTO) to Rutland (RUT) 7.4/10 Good! (1,003 reviews) The lodge absolutely saved us when our Vrbo host ghosted us on our recent trip. Sarah and Tracy were able to work some magic and find available rooms so our group was able to get the 3 rooms we needed completely last minute. We're planning to look here first for all future trips! It's also in an amazing location a few minutes from the mountain, the ski stores, and restaurants Reviewed on Feb 12, 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 1 day 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 ![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 $976 per person Mar 19 - Mar 22 found 13 hours ago Roundtrip non-stop flight included Toronto (YTO) 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 $234 total Mar 1 - Mar 2 includes taxes & fees 7.2/10 Good! (1,001 reviews) The lodge absolutely saved us when our Vrbo host ghosted us on our recent trip. Sarah and Tracy were able to work some magic and find available rooms so our group was able to get the 3 rooms we needed completely last minute. We're planning to look here first for all future trips! It's also in an ... Reviewed on Feb 12, 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! (998 reviews) The staff was very nice and the breakfast was delicious Reviewed on Feb 12, 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 $183 CA $202 total Feb 22 - Feb 23 includes taxes & fees 8/10 Very Good! (1,000 reviews) spacious room Reviewed on Feb 11, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%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=14%2F02%2F2026&endDate=15%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