Title: Pittsfield Chalets from CA $134 | Expedia.ca [Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d6053891.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d6053891.Travel-Guide-VacationRentals)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d6053891.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d6053891.Destination-Travel-Guides) ![Farm](https://images.trvl-media.com/place/6053891/1dbadbe0-84b7-4851-af74-a077f5919903.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Chalets in Pittsfield from CA $134 - ![](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 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6053891&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6053891&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 one month [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6053891&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 two months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6053891&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Pittsfield Chalets No exact matches found, but these alternatives could be just right ## Recommended hotels in Pittsfield ![Exterior](https://images.trvl-media.com/lodging/90000000/89760000/89759100/89759088/9da55179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89760000/89759100/89759088/25a66ca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89760000/89759100/89759088/6636bd76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89760000/89759100/89759088/1a7ae973.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in Pittsfield 10/10 Exceptional (14) "Great stay. Very comfortable, roomy, clean and good overall value." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rob K. CA $198 CA $436 total includes taxes & fees Dec 6 - Dec 7 [](https://www.expedia.ca/Pittsfield-Hotels-Welcome-To-Angel-Mist-Retreat.h89759088.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/121000000/120700000/120691000/120690958/bf91d158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120700000/120691000/120690958/b11f313d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/121000000/120700000/120691000/120690958/f312f5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120700000/120691000/120690958/b385ea09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Pittsfield 10/10 Exceptional (1) "Great host great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) thomas v. CA $135 CA $294 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Pittsfield-Hotels-Charming-In-Town-New-Build-Stylish.h120690958.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/122000000/121380000/121376400/121376376/fa7b6e1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/122000000/121380000/121376400/121376376/801d0f25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121380000/121376400/121376376/acf03781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/122000000/121380000/121376400/121376376/f2ea0cd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bed & Breakfast in Pittsfield CA $377 CA $614 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Pittsfield-Hotels-Pine-Tree-Trail-Lodge.h121376376.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/122000000/121710000/121709900/121709874/d8edb774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121710000/121709900/121709874/579b86fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/122000000/121710000/121709900/121709874/8b35343e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/122000000/121710000/121709900/121709874/257fce69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Pittsfield CA $230 CA $415 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Pittsfield-Hotels-Pine-Tree-Trail-Lodge.h121709874.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/123000000/122540000/122532400/122532368/f12492ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122540000/122532400/122532368/a2a52711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/123000000/122540000/122532400/122532368/8a0adde7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/123000000/122540000/122532400/122532368/b5badf65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Pittsfield CA $195 CA $461 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Pittsfield-Hotels-Downtown-Loft-Pittsfield-Furnished-1BR-Wi-Fi.h122532368.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/123000000/122540000/122532400/122532385/e7b03ac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/123000000/122540000/122532400/122532385/6dba2637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/123000000/122540000/122532400/122532385/93a8c173.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122540000/122532400/122532385/16ed56a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Pittsfield CA $200 CA $466 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Pittsfield-Hotels-Riverside-Loft-Cozy-1BR-W-Sebasticook-River-Views-Trail-Access-Wi-Fi.h122532385.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/123000000/122540000/122532400/122532373/6dc4e39c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122540000/122532400/122532373/04c3bd17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/123000000/122540000/122532400/122532373/0d8a7f66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122540000/122532400/122532373/2a492be5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Pittsfield CA $195 CA $461 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Pittsfield-Hotels-RiverBend-Loft-Modern-Stay-Near-ATV-Snowmobile-Trails.h122532373.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/802200/802109/30bfd3ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/810000/802200/802109/d5d283f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/810000/802200/802109/3e05873b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/802200/802109/0b519be7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Waterville - North by IHG 8.6/10 Excellent (855) "The front desk person when we checked in was amazing. Breakfast was awesome, room was clean! Would stay here again. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Jennifer CA $123 CA $134 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Augusta-Hotels-Holiday-Inn-Express-Suites-Waterville-North.h802109.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/19700/19607/cd463558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Traditional Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/20000/19700/19607/cd7192ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/19700/19607/26e29a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/1000000/20000/19700/19607/0fbc096a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fireside Inn & Suites Waterville 8.8/10 Excellent (1002) "Clean room and friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie CA $142 CA $155 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Augusta-Hotels-Fireside-Inn-Suites-Waterville.h19607.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/72000000/71560000/71556000/71555928/e20f7901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/72000000/71560000/71556000/71555928/5778ded9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free toiletries, hair dryer, towels, soap](https://images.trvl-media.com/lodging/72000000/71560000/71556000/71555928/d53a654b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71560000/71556000/71555928/6685e6ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel in Waterville 8.6/10 Excellent (502) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacqueline CA $145 CA $158 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Waterville-Hotels-The-Elmwood.h71555928.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/6000000/5500000/5490200/5490125/856a318a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, 2 Queen Beds, Kitchenette](https://images.trvl-media.com/lodging/6000000/5500000/5490200/5490125/88d7b3a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/6000000/5500000/5490200/5490125/34e1ef95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, wheelchair access](https://images.trvl-media.com/lodging/6000000/5500000/5490200/5490125/26e7b291.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel in Skowhegan 9.0/10 Wonderful (563) "Our room was neat and clean. The entire staff was very friendly and courteous. We would stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $140 CA $152 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Skowhegan-Hotels-The-Towne-Motel.h5490125.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/730000/721100/721075/c8749634.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/730000/721100/721075/9c236326.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, in-room safe, individually furnished](https://images.trvl-media.com/lodging/1000000/730000/721100/721075/a7f4c66b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/730000/721100/721075/3c11b972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Waterville 9.2/10 Wonderful (590) "Amazing breakfast, quiet and easy parking. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samantha CA $178 CA $194 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Augusta-Hotels-Hampton-Inn-Waterville.h721075.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22100/22003/3f6f3bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/30000/22100/22003/faa38925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/22100/22003/4e706248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/22100/22003/826424a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Waterville Grand Hotel 7.4/10 Good (1000) "Very helpful staff and a wonderful breakfast included." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pat CA $148 CA $161 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Augusta-Hotels-Best-Western-Plus-Waterville-Grand-Hotel.h22003.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/45000000/44010000/44000200/44000158/f040f57d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/45000000/44010000/44000200/44000158/a8536b57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room](https://images.trvl-media.com/lodging/45000000/44010000/44000200/44000158/1c78e329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/45000000/44010000/44000200/44000158/47d16211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel in Canaan 9.8/10 Exceptional (51) "Room was very clean and the beds were extremely comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $172 CA $188 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Canaan-Hotels-Canaan-Motel.h44000158.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1330000/1327400/1327380/fb360cb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1330000/1327400/1327380/dcf71e73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1330000/1327400/1327380/e12a694a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1330000/1327400/1327380/e3ae96bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel in Waterville 6.8/10 (529) "Very clean room and walls were thick-it was quiet." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melody CA $127 CA $138 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Augusta-Hotels-Budget-Host-Airport-Inn.h1327380.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/77000000/76995400/76995336/f312599a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/77000000/76995400/76995336/df06a28f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/77000000/76995400/76995336/0e7387ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/77000000/76995400/76995336/4eb6a4b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Skowhegan 9.8/10 Exceptional (50) "Great place to stay. Highly recommend. Owner was very kind and helpful. Cabin was worth the money." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sue CA $141 CA $297 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Skowhegan-Hotels-Free-Private-Parking.h76995336.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/115000000/114720000/114717300/114717254/f4aad0c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room (Self Check-in with Virtual Front Desk)](https://images.trvl-media.com/lodging/115000000/114720000/114717300/114717254/6846c6f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/115000000/114720000/114717300/114717254/w3000h1685x0y0-cdf42907.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room (Self Check-in with Virtual Front Desk)](https://images.trvl-media.com/lodging/115000000/114720000/114717300/114717254/85cdddd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Skowhegan By Kasa 8.6/10 Excellent (47) "Amazinf stay overall" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARK CA $154 CA $168 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Skowhegan-Hotels-The-Skowhegan-By-Kasa.h114717254.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/97000000/96970000/96963600/96963504/9db45a63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/97000000/96970000/96963600/96963504/2871f62b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96970000/96963600/96963504/5e14a5ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96970000/96963600/96963504/ace8d184.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Hartland 10/10 Exceptional (1) "It was a clean and quiet room. The property was also clean and quiet. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah F. CA $127 CA $231 total includes taxes & fees Dec 6 - Dec 7 [](https://www.expedia.ca/Hartland-Hotels-ON-THE-GO.h96963504.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107170000/107166600/107166584/e831f97a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/108000000/107170000/107166600/107166584/ae97826a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/108000000/107170000/107166600/107166584/076ab3d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107170000/107166600/107166584/45db57fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Oakland 9.0/10 Wonderful (9) "Host was very accommodating " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maureen CA $114 CA $270 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Oakland-Hotels-The-Heart-Of-The-Belgrade-Lakes.h107166584.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113950000/113946100/113946059/a00de8ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113950000/113946100/113946059/917b7fbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113950000/113946100/113946059/efd3e83c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/114000000/113950000/113946100/113946059/2d52a61e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Oakland 10/10 Exceptional (8) "Great stay. Would stay here again if in the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda M. CA $170 CA $322 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Oakland-Hotels-Sister-A-Frame-In-Woods-B.h113946059.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=2025-12-10&endDate=2025-12-11®ionId=6053891&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_6053891) ![](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.d6053891-aaChalets.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Chalets.d6053891-aaChalets.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![Fireside Inn & Suites Waterville](https://images.trvl-media.com/lodging/1000000/20000/19700/19607/0fbc096a_y.jpg) ### Fireside Inn & Suites Waterville 10/10 Excellent "GREAT staff!" [](https://expedia.ca/Augusta-Hotels-Fireside-Inn-Suites-Waterville.h19607.Hotel-Information) ![Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore](https://images.trvl-media.com/lodging/108000000/107350000/107340300/107340207/20d8d18f_y.jpg) ### Lakefront 3 bedroom pet friendly on Messalonskee. Relax, rejuvenate, and restore 10/10 Excellent "The location was perfect. Very quiet and nice to see the sunrise over the lake. It was too cold for us to enjoy the lake in Nov., but it looks like a fun place to come back to in the summer. Beds were very comfortable. " [](https://expedia.ca/Oakland-Hotels-Lakefront-3-Bedroom-Pet-Friendly-On-Messalonski.h107340207.Hotel-Information) ![Holiday Inn Express & Suites Waterville - North by IHG](https://images.trvl-media.com/lodging/1000000/810000/802200/802109/d5d283f3_y.jpg) ### Holiday Inn Express & Suites Waterville - North by IHG 10/10 Excellent "Clean" [](https://expedia.ca/Augusta-Hotels-Holiday-Inn-Express-Suites-Waterville-North.h802109.Hotel-Information) ![Hampton Inn Waterville](https://images.trvl-media.com/lodging/1000000/730000/721100/721075/3c11b972_y.jpg) ### Hampton Inn Waterville 10/10 Excellent "B" [](https://expedia.ca/Augusta-Hotels-Hampton-Inn-Waterville.h721075.Hotel-Information) ![Budget Host Airport Inn](https://images.trvl-media.com/lodging/2000000/1330000/1327400/1327380/83a31218_y.jpg) ### Budget Host Airport Inn 10/10 Excellent "Very clean room and walls were thick-it was quiet." [](https://expedia.ca/Augusta-Hotels-Budget-Host-Airport-Inn.h1327380.Hotel-Information) ![Sister A-Frame in Woods B](https://images.trvl-media.com/lodging/114000000/113950000/113946100/113946059/a00de8ac_y.jpg) ### Sister A-Frame in Woods B 10/10 Excellent "Perfect for Colby visits" [](https://expedia.ca/Oakland-Hotels-Sister-A-Frame-In-Woods-B.h113946059.Hotel-Information) ![The Skowhegan By Kasa](https://images.trvl-media.com/lodging/115000000/114720000/114717300/114717254/f4aad0c9_y.jpg) ### The Skowhegan By Kasa 10/10 Excellent "Amazinf stay overall" [](https://expedia.ca/Skowhegan-Hotels-The-Skowhegan-By-Kasa.h114717254.Hotel-Information) ![Lockwood Hotel](https://images.trvl-media.com/lodging/79000000/78100000/78095000/78094968/d4c480e1_y.jpg) ### Lockwood Hotel 10/10 Excellent "Everything" [](https://expedia.ca/Waterville-Hotels-Lockwood-Hotel.h78094968.Hotel-Information) ![The Elmwood](https://images.trvl-media.com/lodging/72000000/71560000/71556000/71555928/6685e6ca_y.jpg) ### The Elmwood 10/10 Excellent "Excellent. Third time staying there and no regrets!" [](https://expedia.ca/Waterville-Hotels-The-Elmwood.h71555928.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Chalets information | Number of reviews | 5,215 | | --- | --- | | Accommodation | 1 Chalets | | Lowest Price | CA $134 | | Highest Price | CA $614 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [4 Star Hotels in Dixmont](https://www.expedia.ca/4Star-Dixmont-Hotels.s40-0-d553248635975849550.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Detroit](https://www.expedia.ca/5Star-Detroit-Hotels.s50-0-d6333765.Travel-Guide-Filter-Hotels) - [Bangor Hotels](https://www.expedia.ca/Bangor-Hotels.d6050918.Travel-Guide-Hotels) - [Capsule Hotels in Bar Harbor](https://www.expedia.ca/Bar-Harbor-Capsule-Hotels.d561-aaCapsuleHotels.Travel-Guide-Accommodation) - [Condo Rentals in Burnham](https://www.expedia.ca/Burnham-Condos.d553248635975876553-aaCondos.Travel-Guide-Accommodation) - [Burnham Hotels](https://www.expedia.ca/Burnham-Hotels.d553248635975876553.Travel-Guide-Hotels) - 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