Title: Pittsfield Condo Rentals from CA $625 | Expedia.ca [Hotels in Pittsfield](https://expedia.ca/Pittsfield-Hotels.d553248635975875351.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.ca/Pittsfield-Vacation-Rentals.d553248635975875351.Travel-Guide-VacationRentals)[Pittsfield Car Rentals](https://expedia.ca/Car-Rentals-In-Pittsfield.d553248635975875351.Car-Rental-Guide)[Pittsfield Vacation Packages](https://expedia.ca/Pittsfield.d553248635975875351.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Condos Rentals in Pittsfield from CA $625 - ![](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 [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975875351&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 [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635975875351&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248635975875351&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=553248635975875351&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Pittsfield Condo Rentals ![Interior](https://images.trvl-media.com/lodging/74000000/73500000/73496100/73496096/0861e277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, hair dryer, towels, toilet paper](https://images.trvl-media.com/lodging/74000000/73500000/73496100/73496096/35bab6e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73500000/73496100/73496096/d061362d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/74000000/73500000/73496100/73496096/307e53a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peek' n Peak, Camelot Loft Condo, Clymer, NY, 250 Yards to Chair 8, Sleeps 14 Clymer 9.8/10 Exceptional (75) "Great place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Colin S. CA $311 CA $625 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Clymer-Hotels-Peek-N-Peak.h73496096.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/30000000/29630000/29625100/29625062/db41f3d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29630000/29625100/29625062/f8e95426.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/30000000/29630000/29625100/29625062/e13aae49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/30000000/29630000/29625100/29625062/e2a4c43e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winterberry Lodge: Ski In/Out of this slopeside single condo. Best location! Clymer 10/10 Exceptional (76) "This was a great place for a summer vacation. Our extended family rented 3 houses and we could easily walk between them. Streetlights made it easy. There were plenty of activities to satisfy different age groups." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laurel B. CA $684 CA $1,160 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Clymer-Hotels-Winterberry-Lodge-Ski-InOut-Of-This-Slopeside-Single-Condo-Best-Location.h29625062.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=2025-12-22&endDate=2025-12-23®ionId=553248635975875351&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-Condos.d553248635975875351-aaCondos.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Condos.d553248635975875351-aaCondos.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![Hampton Inn & Suites Jamestown](https://images.trvl-media.com/lodging/2000000/1470000/1460400/1460358/dc17262d_y.jpg) ### Hampton Inn & Suites Jamestown 10/10 Excellent "Excellent stay." [](https://expedia.ca/Jamestown-Hotels-Hampton-Inn-Suites-Jamestown.h1460358.Hotel-Information) ![Chautauqua Harbor Hotel - Jamestown](https://images.trvl-media.com/lodging/24000000/23840000/23832100/23832022/a14ac39d_y.jpg) ### Chautauqua Harbor Hotel - Jamestown 10/10 Excellent "Everyone at the hotel was very nice and helpful. would highly recommend " [](https://expedia.ca/Celoron-Hotels-Chautauqua-Harbor-Hotel-Jamestown.h23832022.Hotel-Information) ![Holiday Inn Express & Suites Jamestown by IHG](https://images.trvl-media.com/lodging/10000000/9870000/9866800/9866721/bbe23dc2_y.jpg) ### Holiday Inn Express & Suites Jamestown by IHG 10/10 Excellent "This was A amazing hotel " [](https://expedia.ca/Jamestown-Hotels-Holiday-Inn-Express-Suites-Jamestown.h9866721.Hotel-Information) ![Quality Inn Falconer - Jamestown](https://images.trvl-media.com/lodging/1000000/490000/482700/482632/9964abc5_y.jpg) ### Quality Inn Falconer - Jamestown 10/10 Excellent "Great" [](https://expedia.ca/Jamestown-Hotels-Quality-Inn-Falconer-Jamestown.h482632.Hotel-Information) ![Cobblestone Inn & Suites - Corry](https://images.trvl-media.com/lodging/10000000/9020000/9013700/9013700/c9a7af98_y.jpg) ### Cobblestone Inn & Suites - Corry 10/10 Excellent "Clean, comfortable, quiet, convenient and friendly. Will stay again!" [](https://expedia.ca/Corry-Hotels-Cobblestone-Inn-Suites-Corry.h9013700.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Jamestown](https://images.trvl-media.com/lodging/1000000/980000/978100/978061/3af0ac86_y.jpg) ### La Quinta Inn & Suites by Wyndham Jamestown 10/10 Excellent "perfect! " [](https://expedia.ca/Jamestown-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Jamestown.h978061.Hotel-Information) ![Create your family memories at our nautical lakeside home!](https://images.trvl-media.com/lodging/20000000/19750000/19743200/19743128/683b7bd9_y.jpg) ### Create your family memories at our nautical lakeside home! 10/10 Excellent "Great place, as always!" [](https://expedia.ca/Ashville-Hotels-Create-Your-Family-Memories-At-Our-Nautical-Lakeside-Home.h19743128.Hotel-Information) ![DoubleTree by Hilton Jamestown](https://images.trvl-media.com/lodging/1000000/20000/11500/11426/8fd588ff_y.jpg) ### DoubleTree by Hilton Jamestown 10/10 Excellent "The room was very clean, clean beds, extremely kind and welcoming staff. " [](https://expedia.ca/Jamestown-Hotels-DoubleTree-By-Hilton-Jamestown.h11426.Hotel-Information) ![Eagle's Peak Cozy Cabin](https://images.trvl-media.com/lodging/114000000/113520000/113519600/113519569/14b0fb2c_y.jpg) ### Eagle's Peak Cozy Cabin 10/10 Excellent "Great little place. As advertised. " [](https://expedia.ca/West-Hickory-Hotels-Eagles-Peak-Cozy-Cabin.h113519569.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Condo Rentals information | Number of reviews | 148 | | ----------------- | ---------------- | | Accommodation | 57 Condo Rentals | | Lowest Price | CA $625 | | Highest Price | CA $1,160 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Centerville ](https://www.expedia.ca/4Star-Centerville-Hotels.s40-0-d553248634998807404.Travel-Guide-Filter-Hotels) - [Allegheny National Forest Hotels ](https://www.expedia.ca/Allegheny-National-Forest-Hotels.d6090475.Travel-Guide-Hotels) - [Hotels near Allegheny River ](https://www.expedia.ca/Allegheny-River-Hotels.0-l553248621532660618-0.Travel-Guide-Filter-Hotels) - [Canadohta Lake Hotels ](https://www.expedia.ca/Canadohta-Lake-Hotels.d553248634999200459.Travel-Guide-Hotels) - [Cheap Hotels in Centerville ](https://www.expedia.ca/Centerville-Hotels-Cheap-Hotels.0-0-d553248634998807404-tCheapHotels.Travel-Guide-Filter-Hotels) - 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