Title: Pittsfield Chalets from CA $594 | 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://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Chalets in Pittsfield from CA $594 ![](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 In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=184066&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [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) ## Browse Select Pittsfield Chalets ![Outdoor dining](https://images.trvl-media.com/lodging/64000000/63030000/63026900/63026865/747dbd0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63030000/63026900/63026865/87d01392.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) ![Exterior](https://images.trvl-media.com/lodging/64000000/63030000/63026900/63026865/d42e6390.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dreamy Artist Chalet in Secluded Historic Village East Warren 9.2/10 Wonderful (10) "The chalet was cozy and comfortable. I didn’t not expect this level of comfort in the middle of a forest. The drive from the country road did scare me a little bit. " CA $300 CA $594 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Warren-Hotels-Dreamy-Artist-Chalet-In-Secluded-Historic-Village.h63026865.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/95d08525.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) ![Dining](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/98a04e79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/88000000/87520000/87515500/87515446/b2a8b57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gnome Home Mountain Ski Chalet w/Sauna Killington Stockbridge 10/10 Exceptional (4) "Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!" CA $302 CA $697 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Stockbridge-Hotels-Gnome-Home-Mountain-Ski-Chalet-WSauna-Killington.h87515446.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/102000000/101010000/101007200/101007141/aa314c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101010000/101007200/101007141/f38fe8ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101010000/101007200/101007141/05c45f1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101010000/101007200/101007141/408dd30d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Authentic Log Home in Warren. Ski town. Mountain biking. Short walk to lake. East Warren 10/10 Exceptional (3) "The house is amazing. The hosts clearly love it, and it shows in how well it is set up and stocked. Highly recommended." [](https://www.expedia.ca/Warren-Hotels-Authentic-Log-Home-In-Warren-Ski-Town-Mountain-Biking-Short-Walk-To-Lake.h101007141.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=2025-10-28&endDate=2025-10-29®ionId=184066&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](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](//images.trvl-media.com/lodging/106000000/105670000/105665800/105665795/a55aa0fa_y.jpg) ### My Place Hotel-Randolph VT 10/10 Excellent "Elevator not working " [](https://expedia.ca/My-Place-Hotel-Randolph-VT.h105665795.Hotel-Information) ![Cozy Loft for two with Hot Tub & Mtn Views](//images.trvl-media.com/lodging/60000000/59790000/59784500/59784421/434c8b92_y.jpg) ### Cozy Loft for two with Hot Tub & Mtn Views 10/10 Excellent "The cozy loft was just as advertised. Nice little isolated cabin. We enjoyed our stay. " [](https://expedia.ca/Granville-Hotels-Romantic-Loft-With-Hot-Tub.h59784421.Hotel-Information) ![Brandon Inn](//images.trvl-media.com/lodging/26000000/25190000/25184700/25184647/ec2b6d3b_y.jpg) ### Brandon Inn 10/10 Excellent "The service was excellent. They were very pet friendly. Our dog (mix golden retriever & Afghan hound) was overjoyed with her attention." [](https://expedia.ca/Brandon-Hotels-Brandon-Inn.h25184647.Hotel-Information) ![Killington Mountain Lodge, Tapestry Collection by Hilton](//images.trvl-media.com/lodging/1000000/110000/103700/103640/403a8548_y.jpg) ### Killington Mountain Lodge, Tapestry Collection by Hilton 10/10 Excellent "Clean room , view of the golf area , very good breakfast." [](https://expedia.ca/Killington-Hotels-Killington-Mountain-Lodge.h103640.Hotel-Information) ![Cortina Inn](//images.trvl-media.com/lodging/1000000/30000/27000/27000/aa6e8386_y.jpg) ### Cortina Inn 8/10 Good "All fine " [](https://expedia.ca/Rutland-Hotels-Cortina-Inn.h27000.Hotel-Information) ![The Mountain Inn at Killington](//images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441_y.jpg) ### The Mountain Inn at Killington 10/10 Excellent "Staff very friendly, helpful and welcoming." [](https://expedia.ca/Killington-Hotels-The-Mountain-Inn-At-Killington.h975389.Hotel-Information) ![North Star Lodge and Resort](//images.trvl-media.com/lodging/1000000/190000/185900/185873/0612ebf1_y.jpg) ### North Star Lodge and Resort 10/10 Excellent "Great 👍 " [](https://expedia.ca/Killington-Hotels-North-Star-Lodge-And-Resort.h185873.Hotel-Information) ![Mountain Sports Inn](//images.trvl-media.com/lodging/2000000/1340000/1339900/1339833/7b3b252e_y.jpg) ### Mountain Sports Inn 10/10 Excellent "Clean room, friendly staff " [](https://expedia.ca/Killington-Hotels-Mountain-Sports-Inn.h1339833.Hotel-Information) ![The Jackson ](//images.trvl-media.com/lodging/1000000/190000/181400/181337/f642c888_y.jpg) ### The Jackson 10/10 Excellent "The staff were incredible, so friendly and welcoming. Each night they served wine, cheese and crackers. The overall atmosphere and hospitality was amazing. We hated to leave." [](https://expedia.ca/Woodstock-Hotels-The-Jackson-House-Inn.h181337.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Chalets information | Number of reviews | 13 | | --- | --- | | Accommodation | 34 Chalets | | Lowest Price | CA $594 | | Highest Price | CA $697 | ## 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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