Title: Best Pittsfield Condo Rental in 2026 | Expedia.co.uk [Pittsfield Travel Guide](https://expedia.co.uk/Pittsfield.dx9478)[Hotels in Pittsfield](https://expedia.co.uk/Pittsfield-Hotels.d9478.Travel-Guide-Hotels)[Holiday Rentals in Pittsfield](https://expedia.co.uk/Pittsfield-Holiday-Rentals.d9478.Travel-Guide-HolidayRentals)[Flights to Pittsfield](https://expedia.co.uk/Cheap-Flights-To-Pittsfield.d9478.Travel-Guide-Flights)[Pittsfield Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Pittsfield.d9478.Car-Hire-Guide)[Pittsfield Holidays](https://expedia.co.uk/Pittsfield.d9478.Holidays-City-Breaks) ![](https://images.trvl-media.com/place/9478/b5f5430c-dc51-405d-9103-478c33e1bf14.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/9478/b5f5430c-dc51-405d-9103-478c33e1bf14.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 [17 Apr - 19 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=9478&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [29 May - 31 May](https://www.expedia.co.uk/Hotel-Search?regionId=9478&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [26 Jun - 28 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=9478&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [24 Jul - 26 Jul](https://www.expedia.co.uk/Hotel-Search?regionId=9478&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for 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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property – evening/night](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/9e460e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/8168a5fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Village in the Berkshires [](https://www.expedia.co.uk/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) Williamstown 8.8/10 Excellent (2,323 reviews) "Clean rooms, and very friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amr £96 includes taxes & fees 12 Apr - 13 Apr [](https://www.expedia.co.uk/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/3e2af0e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/34492d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/c1de7213.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/45a94106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7 [](https://www.expedia.co.uk/Hancock-Hotels-2-BR-Condo-Mountain-Views-At-Jiminy-Peak-Sleeps-7.h111663271.Hotel-Information) Hancock 7.6/10 Good (13 reviews) "Great location, right on the mountain's property " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) J S. £256 includes taxes & fees 9 Apr - 10 Apr [](https://www.expedia.co.uk/Hancock-Hotels-2-BR-Condo-Mountain-Views-At-Jiminy-Peak-Sleeps-7.h111663271.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/cdf98da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/7ca2d407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/0b131f87_edited_aacc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/912ebb44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous [](https://www.expedia.co.uk/Hancock-Hotels-2-BR-Jiminy-Peak-W-Mountain-View-Sleeps-7-Gorgeous.h118080540.Hotel-Information) Hancock 9.4/10 Exceptional (3 reviews) "Good stay. Convenient to ski slopes. Thankful for Pet Friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim H. £235 includes taxes & fees 8 Apr - 9 Apr [](https://www.expedia.co.uk/Hancock-Hotels-2-BR-Jiminy-Peak-W-Mountain-View-Sleeps-7-Gorgeous.h118080540.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.co.uk/Hotel-Search?startDate=2026-04-18&endDate=2026-04-19®ionId=9478&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=APART_HOTEL) Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=CABIN) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=VACATION_HOME) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=APARTMENT) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=CONDO) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=COTTAGE) Chalets [](https://www.expedia.co.uk/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=CHALET) ![](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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Condos.d9478-aaCondos.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Condos.d9478-aaCondos.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375_y.jpg) ### Vacation Village in the Berkshires 8/10 Good "Beds could be more updated" [](https://expedia.co.uk/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "The room was lovely as was the restaurant. The place was delightful." [](https://expedia.co.uk/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb_y.jpg) ### Berkshires Untold 4/10 Poor "this is a MOTEL. nothing indicates, in fact, photos are very misleading. Noisy if you are in front on busy highway. AND, allow pets...when asked for room in back, not facing noise, I almost gagged, ok, I did gag at the smell of furry animals that were guests in that room for sure! Fridge needed defrosting badly (so I did it). Bed lamps glued to table so can't raise up to read in bed! Ok, if you are prepared for a motel!" [](https://expedia.co.uk/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/ef3ce5c5_y.jpg) ### Hotel On North 10/10 Excellent "What a lovely room and building. Really enjoyed this hotel. However, the neighborhood outside the hotel was very sketchy and clearly there is an issue with drug addiction in the area. I ate at the restaurant within the hotel and went to and from my car in the gated lot. I enjoyed many other towns in the Berkshires, but Pittsfield was not one of them. Wish this hotel was in a different city, as I would love to stay there again. " [](https://expedia.co.uk/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/6897a130_y.jpg) ### The Red Lion Inn 10/10 Excellent "What a beautiful, unique building. Full of antiques and feels like going back in time. The ride up to my fourth floor room in the 19th century cage elevator was a wonderful touch. Can’t wait to go back again. " [](https://expedia.co.uk/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 8/10 Good "Room temperature was good. Breakfast coukd improve, lack of protein, muffins were not fresh. " [](https://expedia.co.uk/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "this has been absolutely amazing and incredible for incredibly difficult time for our family because of family medical emergency. everyone has been so amazing and beautiful and healing for our loved ones and we are grateful to be close to then" [](https://expedia.co.uk/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Clean, quiet, spacious, comfortable, and lovely furnishings! It was a very relaxing overnight." [](https://expedia.co.uk/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Berkshire Inn](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/b138d836_y.jpg) ### Berkshire Inn 8/10 Good "Great stay " [](https://expedia.co.uk/Pittsfield-Hotels-Berkshire-Inn.h297173.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Condo Rentals information | Number of reviews | 2,339 | | ----------------- | ---------------- | | Accommodation | 46 Condo Rentals | | Lowest Price | £96 | | Highest Price | £256 | ## Frequently asked questions ### How much do condos in Pittsfield cost? ### How many condos are there in Pittsfield? ### Are there any family-friendly condos in Pittsfield? ### Why book your condo in Pittsfield with Expedia? ### How can I find cheap condos in Pittsfield? ### What is there to do in Pittsfield near my condo? ## Explore a world of travel with Expedia - More ways to book - [Book Condo Rentals in Pittsfield on Expedia.com ](https://www.expedia.com/Pittsfield-Condos.d9478-aaCondos.Travel-Guide-Accommodation)