Title: Browse the Best Pittsfield Resorts from CA $384 | 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)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d184066.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pittsfield resorts ![The Jewel | Living area](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/53dd6cd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Jewel ](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/369f7f98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers, beach towels, kayaking](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/80a87dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Jewel | Living room](https://images.trvl-media.com/lodging/10000000/9680000/9673300/9673261/59b85dfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Mountain Top Inn & Resort [](https://www.expedia.ca/Chittenden-Hotels-The-Mountain-Top-Inn-Resort.h9673261.Hotel-Information) Chittenden 9.0/10 Wonderful (104 reviews) "Great resort " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Adam CA $352 CA $384 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Chittenden-Hotels-The-Mountain-Top-Inn-Resort.h9673261.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/fd07b171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna, hot tub, steam room, body treatments, aromatherapy](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/4a1ad77d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/645e5fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodstock Inn & Resort [](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) Woodstock 9.2/10 Wonderful (563 reviews) "Excellent hotel, staff well trained. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christian CA $419 CA $520 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Woodstock-Hotels-Woodstock-Inn-Resort.h25690.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-26&endDate=2026-02-27®ionId=184066&adults=2&lodging=HOTEL_RESORT&sort=RECOMMENDED&openPlayBack=true) ![](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=AA_SPRING_PROMO_184066) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Resort-Hotels.d184066-aaResortHotels.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Resort-Hotels.d184066-aaResortHotels.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg) ### On The River Inn 10/10 Excellent "Room was excellent! Very clean and very comfortable. Bed and comforter were fantastic. Beautiful view in the back . The whole hotel is so nicely dec with antics all around. Have stayed few before will continue to come back. Sent my daughter here as well As a little gift. " [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![The Mountain Inn at Killington](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441_y.jpg) ### The Mountain Inn at Killington 10/10 Excellent "People went out of their way to help My wife needed distilled water for her C-Pap machine the staff went out to store so she could have some. Restaurant was great Room was clean " [](https://expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![My Place Hotel-Randolph VT](https://images.trvl-media.com/lodging/106000000/105670000/105665800/105665795/a55aa0fa_y.jpg) ### My Place Hotel-Randolph VT 10/10 Excellent "Clean room, friendly stas" [](https://expedia.ca/My-Place-Hotel-Randolph-VT.h105665795.Hotel-Information) ![Mountain Sports Inn](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/7b3b252e_y.jpg) ### Mountain Sports Inn 10/10 Excellent "Great time...Great service" [](https://expedia.ca/Killington-Hotels-Mountain-Sports-Inn.h1339833.Hotel-Information) ![Brandon Inn](https://images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/ec2b6d3b_y.jpg) ### Brandon Inn 10/10 Excellent "My family stayed (6 of us) at the Brandon Inn this weekend (2/6-8) to go skiing at Pico and snowshoeing. What a wonderful Inn with old time charm. 200+ year old Inn has an inviting air about it as you learn about its history and evolution as an Inn since the 1700s. Friday and Saturday we were entertained by Ana Guigui, a piano player, who interacts with the audience for her playlist and makes each night feel new and fresh. Amazing and the Innkeeper could not be more accommodating to your needs. Really can’t wait until I can go back and stay there again. Highly recommend. " [](https://expedia.ca/Brandon-Hotels-Brandon-Inn.h25184647.Hotel-Information) ![Best Western Inn & Suites Rutland-Killington](https://images.trvl-media.com/lodging/1000000/20000/16500/16411/9898f616_y.jpg) ### Best Western Inn & Suites Rutland-Killington 10/10 Excellent "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." [](https://expedia.ca/Rutland-Hotels-Best-Western-Inn-Suites-Rutland-Killington.h16411.Hotel-Information) ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "Great room, lovely view and a wonderful town " [](https://expedia.ca/Woodstock-Hotels-The-Shire-Woodstock.h10453651.Hotel-Information) ![North Star Lodge and Resort](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/0612ebf1_y.jpg) ### North Star Lodge and Resort 10/10 Excellent "Staff was helpful and room was clean" [](https://expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ![Comfort Inn Rutland - Killington](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/15d4fef0_y.jpg) ### Comfort Inn Rutland - Killington 10/10 Excellent "Everything was great! The staff were very nice and the free breakfast is legit!" [](https://expedia.ca/Rutland-Hotels-Comfort-Inn-Trolley-Square.h4621.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Resorts information | Number of reviews | 666 | | ----------------- | --------- | | Accommodation | 3 Resorts | | Lowest Price | CA $384 | | Highest Price | CA $520 | ## Frequently asked questions ### What is Pittsfield like for a resort vacation? ### What's a top resort for my stay in Pittsfield? ### What can I do in Pittsfield? ### What's the seasonal weather like in Pittsfield? ### What's the best way to get to and around Pittsfield? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Killington ](https://www.expedia.ca/4Star-Killington-Hotels.s40-0-d10780.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Chittenden ](https://www.expedia.ca/Chittenden-Hotels-Cheap-Hotels.0-0-d184042-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Chittenden ](https://www.expedia.ca/Chittenden-Hotels-Luxury-Hotel.0-0-d184042-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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