Title: Pittsfield Apartment Rentals from CA $251 | Expedia.ca [Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d9478.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d9478.Travel-Guide-VacationRentals)[Flights to Pittsfield](https://expedia.ca/Cheap-Flights-To-Pittsfield.d9478.Travel-Guide-Flights)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d9478.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d9478.Destination-Travel-Guides) ![Pittsfield showing a city](https://images.trvl-media.com/place/9478/b5f5430c-dc51-405d-9103-478c33e1bf14.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Apartment Rentals in Pittsfield - ![](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 [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=9478&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 one month [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=9478&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) In two months [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Pittsfield apartments ![Smart TV](https://images.trvl-media.com/lodging/109000000/108500000/108496800/108496770/a1b50bde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/109000000/108500000/108496800/108496770/47beb459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108500000/108496800/108496770/70fb359a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/109000000/108500000/108496800/108496770/6a37b873.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic corporate apartment in wonderful Pittsfield with AC, WiFi [](https://www.expedia.ca/Pittsfield-Hotels-Chic-Corporate-Apartment-In-Wonderful-Pittsfield-With-AC.h108496770.Hotel-Information) Pittsfield 2.0/10 (1) "THIS. PLACE. IS. A. DUMP. Do NOT STAY HERE under any circumstances." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $185 CA $279 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Pittsfield-Hotels-Chic-Corporate-Apartment-In-Wonderful-Pittsfield-With-AC.h108496770.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/feda3681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/14ef20fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/ea4a2ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/101000000/100960000/100959100/100959022/9c2c97d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Apartment at the Stephentown Hotel [](https://www.expedia.ca/Stephentown-Hotels-Berkshires-Apartment-At-The-Stephentown-Hotel.h100959022.Hotel-Information) Stephentown 10/10 Exceptional (3) "Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matt E. CA $168 CA $334 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Stephentown-Hotels-Berkshires-Apartment-At-The-Stephentown-Hotel.h100959022.Hotel-Information) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/88000000/87820000/87818800/87818778/w1276h853x4y0-c61fbb4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/88000000/87820000/87818800/87818778/94c93760.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87820000/87818800/87818778/e35a54dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87820000/87818800/87818778/6932c0b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Apt in 18th c Berkshire Farmhouse [](https://www.expedia.ca/Lanesborough-Hotels-Charming-Apt-In-18th-C-Berkshire-Farmhouse.h87818778.Hotel-Information) Lanesborough 9.4/10 Exceptional (40) "It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roy CA $185 CA $284 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Lanesborough-Hotels-Charming-Apt-In-18th-C-Berkshire-Farmhouse.h87818778.Hotel-Information) ![1 bedroom, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/a0875211.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/4ee3217b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/edf0cab4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122140000/122136900/122136838/dabbf205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Penthouse Apartment on Park Street [](https://www.expedia.ca/Adams-Hotels-Penthouse-Apartment-On-Park-Street.h122136838.Hotel-Information) Adams 9.6/10 Exceptional (13) "Adams is a beautiful town and looks and feels like the appalachian trail! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) judy r. CA $159 CA $334 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Adams-Hotels-Penthouse-Apartment-On-Park-Street.h122136838.Hotel-Information) ![TV, offices](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413825/4bb2b020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413825/19d02397.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413825/5ac82ed3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413825/5e3915f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Brooks Motel: Exceptional Suite [](https://www.expedia.ca/Hillsdale-Hotels-The-Brooks-Motel-Exceptional-Suite.h104413825.Hotel-Information) Hillsdale 9.2/10 Wonderful (5) "Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deidre H. CA $217 CA $274 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Hillsdale-Hotels-The-Brooks-Motel-Exceptional-Suite.h104413825.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/c3b6bbdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/b3464458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/9c369939.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/74000000/73730000/73729000/73728934/83729050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Rustic Apt in 18th c Berkshire Farmhouse [](https://www.expedia.ca/Lanesborough-Hotels-Cozy-Rustic-Apt-In-18th-C-Berkshire-Farmhouse.h73728934.Hotel-Information) Lanesborough 9.6/10 Exceptional (67) "We had a lovely stay! The studio was comfortable, clean, and just what we needed. Our hosts were friendly and helpful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janice L. CA $185 CA $284 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Lanesborough-Hotels-Cozy-Rustic-Apt-In-18th-C-Berkshire-Farmhouse.h73728934.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/79000000/78540000/78537700/78537603/b5482417.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/79000000/78540000/78537700/78537603/3663d99c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78540000/78537700/78537603/w905h678x0y5-7353a588.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78540000/78537700/78537603/9e312028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat [](https://www.expedia.ca/Hancock-Hotels-Disney-Magic-At-Jiminy-Must-See-Gorgeous-Sleeps-4.h78537603.Hotel-Information) Hancock 9.8/10 Exceptional (18) "We enjoyed our stay in this adorable Disney Themed condo. The attention to detail in the theming was fantastic and the condo was perfect for our February Vacation ski trip." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Allison V. CA $356 CA $577 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Hancock-Hotels-Disney-Magic-At-Jiminy-Must-See-Gorgeous-Sleeps-4.h78537603.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120670000/120662100/120662087/e729958e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/121000000/120670000/120662100/120662087/d565c872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120670000/120662100/120662087/477e18b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/121000000/120670000/120662100/120662087/8ffc6379.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Allen House historic North Adams Home in the Berkshire Mountains [](https://www.expedia.ca/North-Adams-Hotels-The-Allen-House-Historic-North-Adams-Home-In-The-Berkshire-Mountains.h120662087.Hotel-Information) North Adams CA $242 CA $440 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/North-Adams-Hotels-The-Allen-House-Historic-North-Adams-Home-In-The-Berkshire-Mountains.h120662087.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/2788df34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/a7eb284a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/2435c38a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, stereo](https://images.trvl-media.com/lodging/65000000/64430000/64428500/64428459/d5a96942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Bed Berkshire Apt minutes to Jiminy Peak Ski [](https://www.expedia.ca/Stephentown-Hotels-2-Bed-Berkshire-Apt-Minutes-To-Jiminy-Peak-Ski.h64428459.Hotel-Information) Stephentown 8.4/10 Very good (12) "Great location and property. thank you" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine P. CA $187 CA $365 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Stephentown-Hotels-2-Bed-Berkshire-Apt-Minutes-To-Jiminy-Peak-Ski.h64428459.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/ed34618a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/w1008h683x16y0-6785a02b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/0789534a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/w515h679x0y4-819e565e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor [](https://www.expedia.ca/Hancock-Hotels-Mountain-Getaway-Suite-Ski-OnOff-Jiminy-Peak-Fully-Redone-Decor.h124014382.Hotel-Information) Hancock [](https://www.expedia.ca/Hancock-Hotels-Mountain-Getaway-Suite-Ski-OnOff-Jiminy-Peak-Fully-Redone-Decor.h124014382.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95670000/95669000/95668997/17e920ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, travel crib, WiFi](https://images.trvl-media.com/lodging/96000000/95670000/95669000/95668997/44b79f2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95670000/95669000/95668997/d19d4f13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/96000000/95670000/95669000/95668997/e067dc85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Bed Berkshire Getaway @ Stephentown Hotel [](https://www.expedia.ca/Stephentown-Hotels-2-Bed-Berkshire-Getaway-Stephentown-Hotel.h95668997.Hotel-Information) Stephentown 10/10 Exceptional (5) "This place is amazing! It is so clean and updated with lots of amenities! Lots of arcade games in the apartment thatthe whole family enjoyed! It's a quick trip to jimney peak to ski it's just down the road. Great restaurants nearby. Definitely recommend this place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) elizabeth r. CA $241 CA $438 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Stephentown-Hotels-2-Bed-Berkshire-Getaway-Stephentown-Hotel.h95668997.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/949e9107.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/78da5d01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/63833f21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76713300/76713290/643b3865.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous [](https://www.expedia.ca/Hancock-Hotels-Chic-2BR-Suite-On-Jiminy-Mtn-Sleeps-8-Gorgeous.h76713290.Hotel-Information) Hancock 9.6/10 Exceptional (30) "Great and clean property! Very easy to access and good parking too." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Todd A. CA $288 CA $541 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Hancock-Hotels-Chic-2BR-Suite-On-Jiminy-Mtn-Sleeps-8-Gorgeous.h76713290.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/74000000/73420000/73412800/73412761/823ad85e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73420000/73412800/73412761/92299206.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73420000/73412800/73412761/bfd8f88b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/74000000/73420000/73412800/73412761/4fe33b07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bright Boho Apt in 18th c Berkshire Farmhouse [](https://www.expedia.ca/Lanesborough-Hotels-Bright-Boho-Apt-In-18th-C-Berkshire-Farmhouse.h73412761.Hotel-Information) Lanesborough 9.0/10 Wonderful (22) "I loved staying here the weekend with my friends, the owner Patrick was so accommodating and helpful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mckenna d. CA $198 CA $299 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Lanesborough-Hotels-Bright-Boho-Apt-In-18th-C-Berkshire-Farmhouse.h73412761.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/e60e5176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/78a1069e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/w1333h900x16y0-00a84624.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/141e4e93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor [](https://www.expedia.ca/Hancock-Hotels-Gorgeous-Mountain-View-Suite-Ski-OnOff-At-Jiminy-Fully-Redone-Decor.h96837232.Hotel-Information) Hancock 10/10 Exceptional (3) "Stayed one night at one of my favorite ski spots. Will be back again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Neil J. CA $216 CA $414 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Hancock-Hotels-Gorgeous-Mountain-View-Suite-Ski-OnOff-At-Jiminy-Fully-Redone-Decor.h96837232.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786765/3b948672.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, offices](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786765/fe1becd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786765/w1298h680x0y0-b31746a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786765/w992h667x8y0-e5344523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count [](https://www.expedia.ca/Hancock-Hotels-1st-FL-Mtn-View-Woodland-Suite-On-Jiminy-Sleeps-4-Ski-OnOff.h90786765.Hotel-Information) Hancock 9.4/10 Exceptional (6) "Great location. Very nice vacation. Would def go again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth M. [](https://www.expedia.ca/Hancock-Hotels-1st-FL-Mtn-View-Woodland-Suite-On-Jiminy-Sleeps-4-Ski-OnOff.h90786765.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103850000/103845900/103845853/e9c2fca2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/104000000/103850000/103845900/103845853/8250863a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103850000/103845900/103845853/b7039a07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103850000/103845900/103845853/930055e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer [](https://www.expedia.ca/Great-Barrington-Hotels-Close-To-Tanglewood-2BR-King-Bed-Fireplace-Sleeps-6-Mountain-View-Gem.h103845853.Hotel-Information) Great Barrington CA $600 CA $756 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Great-Barrington-Hotels-Close-To-Tanglewood-2BR-King-Bed-Fireplace-Sleeps-6-Mountain-View-Gem.h103845853.Hotel-Information) ![TV, offices](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413821/d82c5676.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413821/fb8075b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413821/70d89edf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413821/3eb645b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Brooks Motel: Exceptional Suite [](https://www.expedia.ca/Hillsdale-Hotels-The-Brooks-Motel-Exceptional-Suite.h104413821.Hotel-Information) Hillsdale 7.0/10 Good (4) "Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John P. CA $217 CA $274 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Hillsdale-Hotels-The-Brooks-Motel-Exceptional-Suite.h104413821.Hotel-Information) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413823/7ca7ac9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413823/a07ad488.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413823/474184ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413823/a4c67e1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brooks Motel: Perfect Suite, Seasonal Waterviews [](https://www.expedia.ca/Hillsdale-Hotels-Brooks-Motel-Perfect-Suite.h104413823.Hotel-Information) Hillsdale 6.0/10 (1) "NO HOT WATER!!! My room had exposed wood not like the photo. Musty smell in living room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joan V. CA $197 CA $251 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Hillsdale-Hotels-Brooks-Motel-Perfect-Suite.h104413823.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119240000/119237000/119236971/87656220.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119240000/119237000/119236971/667aa8e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/120000000/119240000/119237000/119236971/0ca83843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119240000/119237000/119236971/03f8e408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4 [](https://www.expedia.ca/Hancock-Hotels-Luxury-Jiminy-Ski-On-Off-Village-Ctr-Condo-Sleeps4.h119236971.Hotel-Information) Hancock 10/10 Exceptional (1) CA $202 CA $414 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Hancock-Hotels-Luxury-Jiminy-Ski-On-Off-Village-Ctr-Condo-Sleeps4.h119236971.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/250d56fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/0ac89dfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, books](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/69ce761a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/bae121bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor [](https://www.expedia.ca/Hancock-Hotels-Must-See-Pirate-Suite-Ski-OnOff-Jiminy-Mtn-View-Fully-Redone-Decor.h98512708.Hotel-Information) Hancock 10/10 Exceptional (5) "It was great experience and we loved the ammenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carrie C. CA $321 CA $535 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Hancock-Hotels-Must-See-Pirate-Suite-Ski-OnOff-Jiminy-Mtn-View-Fully-Redone-Decor.h98512708.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=2026-01-10&endDate=2026-01-11®ionId=9478&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-Apartments.d9478-aaApartments.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Apartments.d9478-aaApartments.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "The bed was very comfortable. The staff was helpful and courteous" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Staff is incredibly helpful and friendly " [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Our room was spotless and cozy. I was very pleased to be able to control the temperature as I like to sleep in a cool room. The shower and sink products are lovely -- especially the moisturizer for cold weather skin. I cannot speak highly enough about the restaurant -- beautiful decor, delicious cocktails, amazing food, everything we ordered was great!" [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG 10/10 Excellent "Extremely impressed by this hotel. The staff was very friendly and professional. The rooms were so comfortable and high quality everything! Check in and check out was easy. Highly recommend!" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "While waiting for our vallet car due to construction. The hotel staff were engaging and had personal conversations with us. Rooms were good and all staff treated us exceptional. Give them an atta boy on proformance" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Very professional service. Great staff." [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "My stay was great with no problems. " [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Courteous staff " [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "Yes" [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Apartments information | Number of reviews | 233 | | ----------------- | -------------- | | Accommodation | 108 Apartments | | Lowest Price | CA $251 | | Highest Price | CA $577 | ## Frequently asked questions ### What's it like to stay at an apartment in Pittsfield? ### How do you know if an apartment is a good option for your stay? ### What's the best apartment for my stay in Pittsfield? ### How many apartments are there in Pittsfield? ### What will the weather be like in Pittsfield? ### What are the must-see places to visit in Pittsfield? ### What's the best way to get to and around Pittsfield? ## Explore a world of travel with Expedia - 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