Title: Pittsfield Chalets from CA $539 | 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) # Search Chalets in Pittsfield from CA $539 - ![](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 [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pittsfield chalets ![Exterior](https://images.trvl-media.com/lodging/64000000/63030000/63026900/63026865/d42e6390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/64000000/63030000/63026900/63026865/7e228bd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/64000000/63030000/63026900/63026865/a11e6e92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/64000000/63030000/63026900/63026865/1a5b9e22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dreamy Artist Chalet in Secluded Historic Village [](https://www.expedia.ca/Warren-Hotels-Dreamy-Artist-Chalet-In-Secluded-Historic-Village.h63026865.Hotel-Information) East Warren 9.2/10 Wonderful (10) "Everything was beautiful. But for sure needs new mattress and pillows. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeanette R. CA $280 CA $539 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Warren-Hotels-Dreamy-Artist-Chalet-In-Secluded-Historic-Village.h63026865.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/48be0320.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/c33b35a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/98a04e79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/efdfd8b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gnome Home Mountain Ski Chalet w/Sauna Killington [](https://www.expedia.ca/Stockbridge-Hotels-Gnome-Home-Mountain-Ski-Chalet-WSauna-Killington.h87515446.Hotel-Information) Stockbridge 10/10 Exceptional (4) "Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gerald S. CA $337 CA $734 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Stockbridge-Hotels-Gnome-Home-Mountain-Ski-Chalet-WSauna-Killington.h87515446.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89990000/89982100/89982066/400cdd0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89990000/89982100/89982066/1e901d44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/90000000/89990000/89982100/89982066/ecac89c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89990000/89982100/89982066/a250ff08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### BearHaus-Fireplace, HUGE indoor Hot Tub, Sleeps 14 [](https://www.expedia.ca/Killington-Hotels-BearHaus-New-Reno.h89982066.Hotel-Information) Killington 9.6/10 Exceptional (5) "Great property - excellent hosts. Close to mountain and restaurants" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric D. CA $621 CA $1,453 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Killington-Hotels-BearHaus-New-Reno.h89982066.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/81000000/80820000/80813400/80813386/8d12bb48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/81000000/80820000/80813400/80813386/39882109.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/81000000/80820000/80813400/80813386/2c0a2719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/81000000/80820000/80813400/80813386/aaabeade.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kilbourne Lodge ︙ Cozy Mid-Mod ︙ Fireplace ︙ Ski Shuttle [](https://www.expedia.ca/Killington-Hotels-Kilbourne-LodgeMid-Century-Chalet-Killington-RdPet-Family-Friendly.h80813386.Hotel-Information) The Woods 9.4/10 Exceptional (8) "Great stay, thanks!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bret R. CA $1,016 CA $1,734 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Killington-Hotels-Kilbourne-LodgeMid-Century-Chalet-Killington-RdPet-Family-Friendly.h80813386.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=2025-12-25&endDate=2025-12-26®ionId=184066&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-14&d2=2026-03-14&lodging=CABIN) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-14&d2=2026-03-14&lodging=VACATION_HOME) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-14&d2=2026-03-14&lodging=APARTMENT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-14&d2=2026-03-14&lodging=CONDO) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-14&d2=2026-03-14&lodging=COTTAGE) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-14&d2=2026-03-14&lodging=CHALET) Villas [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Vermont%2C+United+States+of+America®ionId=184066&latLong=43.772289%2C-72.812881&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-14&d2=2026-03-14&lodging=VILLA) ![](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-Chalets.d184066-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Chalets.d184066-aaChalets.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![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 "We stopped at this hotel on our way up to Stowe Mountain traveling from NJ. The room was affordable, modern, & clean. Our hotel room was a pleasant surprise. We had a full size fridge, microwave, oven, & kitchen in there. We stayed in a hearing impaired room that had a very spacious bathroom. We didn’t notice a lot of food options other than a McDonalds and convenience store about half a mile away. The lobby had a lot of amenities like snacks and other items you may have forgot to pack but were on the pricey side (ex. A bottle of Diet Coke was $4). We would definitely stay again." [](https://expedia.ca/My-Place-Hotel-Randolph-VT.h105665795.Hotel-Information) ![The Shire Woodstock](https://images.trvl-media.com/lodging/11000000/10460000/10453700/10453651/3700fd69_y.jpg) ### The Shire Woodstock 10/10 Excellent "After reading reviews I was pleasantly surprised of the high quality of our room. We had a premium king room in the river house. Was large and bathroom was also large with a jacuzzi tub, shared balcony overlooking the river. Walking distance to town, shops and restaurants. Only stayed one night for a wedding in town but overall had a very good experience!" [](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 "Location is very convenient. Service as described online." [](https://expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.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 "We had a great weekend stay. Staff was great. We had a nice clean room, the continental breakfast had a great selection and the restaurant was really nice, food was delicious and so very convenient. We really enjoyed sitting by the fire in the lounge type room. And although we didnt bring our dog i was happy to see other dogs around and the fact that everyone is respectful, you wouldn't know that there were dogs staying there if you didn't see them. " [](https://expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![Cortina Inn](https://images.trvl-media.com/lodging/1000000/30000/27000/27000/aa6e8386_y.jpg) ### Cortina Inn 10/10 Excellent "Warm" [](https://expedia.ca/Rutland-Hotels-Cortina-Inn.h27000.Hotel-Information) ![Killington Mountain Lodge, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/403a8548_y.jpg) ### Killington Mountain Lodge, Tapestry Collection by Hilton 10/10 Excellent "Clean room and bathroom. Alex at the desk was very helpful and nice. " [](https://expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![On The River Inn](https://images.trvl-media.com/lodging/9000000/8320000/8318900/8318875/fa7b6946_y.jpg) ### On The River Inn 10/10 Excellent "Excellent place to stay anytime of the year." [](https://expedia.ca/Woodstock-Hotels-506-On-The-River-Inn.h8318875.Hotel-Information) ![Brandon Inn](https://images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/ec2b6d3b_y.jpg) ### Brandon Inn 10/10 Excellent "I went to the Brandon Inn while traveling and loved it. It was an Historic town and building; simply charming. Staff was lovely and my room was quiet. I would totally go back again. " [](https://expedia.ca/Brandon-Hotels-Brandon-Inn.h25184647.Hotel-Information) ![Mountain Sports Inn](https://images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/7b3b252e_y.jpg) ### Mountain Sports Inn 10/10 Excellent "Everything was awesome. Especially breakfast. " [](https://expedia.ca/Killington-Hotels-Mountain-Sports-Inn.h1339833.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Chalets information | Number of reviews | 18 | | ----------------- | ---------- | | Accommodation | 34 Chalets | | Lowest Price | CA $539 | | Highest Price | CA $1,734 | ## 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) - [Mountain Hotels in Chittenden ](https://www.expedia.ca/Chittenden-Hotels-Mountain-Hotels.0-0-d184042-tMountainHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Chittenden ](https://www.expedia.ca/Chittenden-Hotels-Pet-Friendly-Hotel.0-0-d184042-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - 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