Title: Pittsfield Condo Rentals from CA $157 | 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://a.travel-assets.com/findyours-php/viewfinder/images/res70/105000/105316-The-Berkshires.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Condos Rentals in Pittsfield from CA $157 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Pittsfield Condo Rentals ![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/03675fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/64adfbe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/18127ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Village in the Berkshires Williamstown 8.6/10 Excellent (2020) "All around loved everything about the place! " CA $127 CA $157 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/34492d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/82468102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/d1c43c74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/a111c8ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7 Hancock 8.0/10 Very good (8) "Cozy little condo, good for a group of four or five. We stayed there with my two kids 8 &10 and wife. It’s a nice place overall we had a great time. It is a short drive to the slopes, which is fine as long as you have a car but you still need to park at the inn" CA $206 CA $476 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Hancock-Hotels-2-BR-Condo-Mountain-Views-At-Jiminy-Peak-Sleeps-7.h111663271.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/d5e215b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/b5c16e1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/cdf98da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/w911h606x0y0-40def80c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous Hancock 8.0/10 Very good (1) "very nice and roomy! really enjoyed." CA $188 CA $416 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Hancock-Hotels-2-BR-Jiminy-Peak-W-Mountain-View-Sleeps-7-Gorgeous.h118080540.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1080h783x0y5-9ee375ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/a814c17c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1075h808x0y2-de6afae7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/c54967a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### UNIQUE - 1BR Country Condo @ Jiminy Peak Hancock 10/10 Exceptional (13) "Clean and quiet, nicely decorated! " CA $137 CA $431 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Hancock-Hotels-UNIQUE-Gnome-Themed-1BR-Condo.h74312811.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89990000/89988500/89988465/2a7da31c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, table tennis](https://images.trvl-media.com/lodging/90000000/89990000/89988500/89988465/83e307e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/90000000/89990000/89988500/89988465/23c030ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/90000000/89990000/89988500/89988465/72689c3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski-In/Ski-Out at Jiminy Peak in the Country Inn Hancock 9.0/10 Wonderful (27) "We had a great experience with this rental. Nice location for skiing on and off the mountain and close to the heart of the ski facility. " [](https://www.expedia.ca/Hancock-Hotels-Ski-InSki-Out-At-Jiminy-Peak-In-The-Country-Inn.h89988465.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66550000/66542300/66542211/b6a3217f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/67000000/66550000/66542300/66542211/w1852h1242x5y0-22a5cbf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/67000000/66550000/66542300/66542211/w2916h2186x0y0-1cc358cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66550000/66542300/66542211/f2860ac4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1 Hancock 10/10 Exceptional (40) "3rd time staying here. The host is great, the place is clean, and the location couldn't be better!" [](https://www.expedia.ca/Hancock-Hotels-Ski-In.h66542211.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873953/8e8a723a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873953/9146e770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873953/884f571c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873953/6d6a9392.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Wyndham Bentley Brook Resort - 2 Bedroom Hancock [](https://www.expedia.ca/Hancock-Hotels-Club-Wyndham-Bentley-Brook-Resort-2-Bedroom.h112873953.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873966/7f4d0925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873966/7ca9c813.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873966/b637468e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games, DVD player, table tennis](https://images.trvl-media.com/lodging/113000000/112880000/112874000/112873966/9d8fe636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Wyndham Bentley Brook Resort - 2 Bedroom Hancock [](https://www.expedia.ca/Hancock-Hotels-Club-Wyndham-Bentley-Brook-Resort-2-Bedroom.h112873966.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/71000000/70580000/70570900/70570807/ee219097.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/71000000/70580000/70570900/70570807/b0766675.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70580000/70570900/70570807/4de3fdd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70580000/70570900/70570807/d459f5e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook Hancock 10/10 Exceptional (13) "Great location, all the amenities were available to us. Right on the base of the mountain. Thx for the stay! " [](https://www.expedia.ca/Hancock-Hotels-The-Berkshires-Jiminy-Mountains-Club-Wyndham-Bentley-Brook.h70570807.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/22f66f00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/589cb0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/f9dd0939.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593874/dd2937db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tranquil Lakeside Escape in the Berkshires Lenox 10/10 Exceptional (1) "perfect location to go everywhere in the Berkshires" [](https://www.expedia.ca/Lenox-Hotels-Tranquil-Lakeside-Escape-In-The-Berkshires.h116593874.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593867/dba923f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593867/d1155757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593867/e0957bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/117000000/116600000/116593900/116593867/25c39568.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful 1BR Condo with Pond View Lenox 8.0/10 Very good (2) "Beautiful grounds and views and so close to Tanglewood! We had a great time. Apartment was clean and very private. It was quiet and quaint.The only issue I should mention is the carpeting; seemed a bit dump and not very appealing." [](https://www.expedia.ca/Lenox-Hotels-Peaceful-1BR-Condo-With-Pond-View.h116593867.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/113000000/112060000/112056600/112056501/w1302h976x2y0-070db8a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112060000/112056600/112056501/61f2e1e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112060000/112056600/112056501/e2d5b928.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112060000/112056600/112056501/w1302h978x0y0-88bd51f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool Hancock 10/10 Exceptional (3) "Good base for Berkshires, responsive host, good rates, secure." [](https://www.expedia.ca/Hancock-Hotels-Family-Friendly-Mountain-Retreat-At-Jiminy-Peak.h112056501.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78360000/78357200/78357134/c6d14d4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78360000/78357200/78357134/d000d79a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78360000/78357200/78357134/w1656h1242x0y0-1afe4a3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78360000/78357200/78357134/w3836h2878x0y0-b2743c25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2 Hancock 10/10 Exceptional (33) "Everything was spot on. Will be back!!" [](https://www.expedia.ca/Hancock-Hotels-SKI-IN.h78357134.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74710000/74703700/74703683/9c584984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/75000000/74710000/74703700/74703683/w1170h870x0y0-ad76d082.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74710000/74703700/74703683/w1170h846x0y0-b5c1c36e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74710000/74703700/74703683/0f2b3928.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5 Hancock 10/10 Exceptional (6) "It was exactly as described, perfect for a family stay with easy ski on and off. I was pleasantly surprised with all the amenities of the property. Would stay again!" [](https://www.expedia.ca/Hancock-Hotels-Ski-In-Ski-Out-Deluxe-1-Bedroom-Condo.h74703683.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95480000/95472300/95472240/45301dba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/96000000/95480000/95472300/95472240/ae75dac8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95480000/95472300/95472240/b1af2160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/96000000/95480000/95472300/95472240/1332cd72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS! Hancock 10/10 Exceptional (12) "We'll be back!" [](https://www.expedia.ca/Hancock-Hotels-SKI-IN.h95472240.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/24000000/23320000/23314900/23314836/05c95295.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/24000000/23320000/23314900/23314836/e23fc203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/24000000/23320000/23314900/23314836/9f6ecfb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23320000/23314900/23314836/219cb08f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY Hancock 9.6/10 Exceptional (17) "Perfect place for our annual ski-cation. Great accommodations minutes from Jiminy Peak. Equipped with everything you need for a great vacation!" [](https://www.expedia.ca/Lanesborough-Hotels-4-Level-WINTER-SKI-RENTAL-LOOKING-4-SEASONAL-RENTER-1-MILE-OFF-SLOPES-OF-JIMINEY.h23314836.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112050000/112048700/112048690/e2552b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112050000/112048700/112048690/8508dba2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112050000/112048700/112048690/b5adc5ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112050000/112048700/112048690/b9e96575.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths Hancock [](https://www.expedia.ca/Hancock-Hotels-Escape-To-The-Heart-Of-Jiminy-Peak-Ski-InSki-Out-Apartment-With-Stunning-Views.h112048690.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/111000000/110320000/110311200/110311175/1b5c2068.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/111000000/110320000/110311200/110311175/c7bbad58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games, DVD player, table tennis](https://images.trvl-media.com/lodging/111000000/110320000/110311200/110311175/54bf77ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/111000000/110320000/110311200/110311175/f57098a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Wyndham Bentley Brook Resort - 2 Bedroom Hancock 6.0/10 (2) "Great spot for family ski trip. Location was great. Condo and amenities were great. Overall super happy and would stay again. " [](https://www.expedia.ca/Hancock-Hotels-Club-Wyndham-Bentley-Brook-Resort-2-Bedroom.h110311175.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113400000/113390100/113390092/fa250819.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/114000000/113400000/113390100/113390092/9a2668ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/114000000/113400000/113390100/113390092/d08fa1e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games, DVD player, table tennis](https://images.trvl-media.com/lodging/114000000/113400000/113390100/113390092/d8c6ad82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Wyndham Bentley Brook Resort - 2 Bedroom Hancock [](https://www.expedia.ca/Hancock-Hotels-Club-Wyndham-Bentley-Brook-Resort-2-Bedroom.h113390092.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113500000/113492900/113492900/e3c0b681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/114000000/113500000/113492900/113492900/a4378c73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113500000/113492900/113492900/af5a3eef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games, DVD player, table tennis](https://images.trvl-media.com/lodging/114000000/113500000/113492900/113492900/7193e718.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Wyndham Bentley Brook Resort - 2 Bedroom Hancock [](https://www.expedia.ca/Hancock-Hotels-Club-Wyndham-Bentley-Brook-Resort-2-Bedroom.h113492900.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=2025-10-08&endDate=2025-10-09®ionId=9478&adults=2&lodging=CONDO&sort=RECOMMENDED&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-Condos.d9478-aaCondos.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Condos.d9478-aaCondos.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![Comfort Inn & Suites East Greenbush - Albany](//images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/ea181a79_y.jpg) ### Comfort Inn & Suites East Greenbush - Albany 10/10 Excellent "The lobby was different and dramatic. Liked that the eating area was raised above it on the second floor and gave a view of the hotel and surrounding scenery. Breakfast was adequate - nothing special but good. We did have a bit of trouble with the toilet in our room which we were able to fix without calling the desk. Would definitely stay there again if we return to visit." [](https://expedia.ca/Albany-Hotels-Comfort-Inn-Suites-East-Greenbush-Albany.h1052319.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Totally perfect for mass mocha" [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Hotel On North](//images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "everything-loved it!" [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](//images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Valerie at the front desk and who checked me in was above and beyond in customer service. She checked to see if I had a IGH account—which I did but had forgotten, and reminded me about the points and promotions. This Holiday Inn is a well managed property. Thank you" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](//images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "We stayed for 5 nights and really enjoyed the surroundings and the drive to the property. The area is peaceful and quiet, with plenty to do for kids, including a mountain hike that even our 2- and 6-year-olds managed well. The grounds are beautiful for photos, very well maintained, and we often saw the crew cleaning and painting the sidewalks. I booked 2 suites, which were a good size for a family of four and offered plenty of space. The only downsides were that check-in felt a bit tedious it took several tries to swipe my card and there was no housekeeping service or follow-up to check on amenities during our stay. A self check-in option would make things smoother. Overall, we loved the quietness, the family-friendly activities, and the clean, well-kept property. With a few improvements in guest service, this could easily be a 5-star experience." [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Excellent location. Friendly staff. " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](//images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "Perfect for an overnight for the Tanglewood concert" [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "A great place if you appreciate and like history. The lobby is filled with antiques and the porch is great to rock in a chair and sip some wine. Parking is no issue and you can walk to local restaurants and shops. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](//images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG 10/10 Excellent " To whom it may concern, My wife & I were blessed beyond measures with Chris the recepcionista who was an amazing incredible human being who treated us like family. We needed some direction to southbridge Ma. He explain to us the best way to get there and back to the hotel. Also the other gentleman working along side of him also assisted us as well. Thank you for this beautiful experience and to let you know that we will come again. Please give our love to the precious lady housekeeper who blessed us as well. " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Condo Rentals information | Number of reviews | 2,147 | | --- | --- | | Accommodation | 67 Condo Rentals | | Lowest Price | CA $157 | | Highest Price | CA $476 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [B&B in Berkshire County](https://www.expedia.ca/Berkshire-County-Bed-And-Breakfast.d553248635083901436-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Berkshire County](https://www.expedia.ca/Berkshire-County-Chalets.d553248635083901436-aaChalets.Travel-Guide-Accommodation) - [Inns in Berkshire County](https://www.expedia.ca/Berkshire-County-Inns.d553248635083901436-aaInns.Travel-Guide-Accommodation) - [Resorts in Berkshire County](https://www.expedia.ca/Berkshire-County-Resort-Hotels.d553248635083901436-aaResortHotels.Travel-Guide-Accommodation) - 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[Flights to Lenox](https://www.expedia.ca/Cheap-Flights-To-Lenox.d8587.Travel-Guide-Flights) - [Flights from Lenox](https://www.expedia.ca/lp/flights/8587/flights-from-lenox) - [Flights from Bangor (BGR) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/bgr/psf/bangor-to-pittsfield) - [Flights from Boston (BOS) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/bos/psf/boston-to-pittsfield) - [Flights from Ithaca (ITH) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/ith/psf/ithaca-to-pittsfield) - [Flights from Plattsburgh (PBG) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/pbg/psf/plattsburgh-to-pittsfield) - [Flights from Phoenix (PHX) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/phx/psf/phoenix-to-pittsfield) - [Flights from Richmond (RIC) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/ric/psf/richmond-to-pittsfield) - [Flights from Seattle (SEA) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/sea/psf/seattle-to-pittsfield) - [Flights from Toronto (YYZ) to Pittsfield (PSF)](https://www.expedia.ca/lp/flights/yyz/psf/toronto-to-pittsfield) - [Canoe Meadows Wildlife Sanctuary](https://www.expedia.ca/Canoe-Meadows-Wildlife-Sanctuary-Pittsfield.d553248621532665285.Vacation-Attraction) - [Hancock Shaker Village](https://www.expedia.ca/Hancock-Shaker-Village-Pittsfield.d6091849.Vacation-Attraction) - [Lenox Library](https://www.expedia.ca/Lenox-Library-Lenox.d553248621532665268.Vacation-Attraction) - [Richmond Vacations](https://www.expedia.ca/Richmond.d151138.Destination-Travel-Guides) - [Ventfort Hall Mansion and Gilded Age Museum](https://www.expedia.ca/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Vacation-Attraction) - [Avis Rental Cars in Lenox](https://www.expedia.ca/Avis-Car-Rentals-In-Lenox.d8587-c41.Car-Rental-Guide-Suppliers) - [Car rental Hancock](https://www.expedia.ca/Car-Rentals-In-Hancock.d112303.Car-Rental-Guide) - [Car rentals near Jiminy Peak Mountain Resort](https://www.expedia.ca/Car-Rentals-In-Jiminy-Peak-Mountain-Resort.d553248621532665536.Car-Rental-Guide) - [Car rental Lenox](https://www.expedia.ca/Car-Rentals-In-Lenox.d8587.Car-Rental-Guide) - [Rental cars Pittsfield Municipal airport](https://www.expedia.ca/Car-Rentals-In-Pittsfield-Municipal.d6031274.Car-Rental-Guide) - [Dalton Vacation Rentals](https://www.expedia.ca/Dalton-Vacation-Rentals.d6911.Travel-Guide-VacationRentals) - [Book Condo Rentals in Pittsfield on Expedia.com](https://www.expedia.com/Pittsfield-Condos.d9478-aaCondos.Travel-Guide-Accommodation)