Title: Pittsfield Villas from CA $107 | 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 Pittsfield Villa Rentals from CA $107 - ![](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 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [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 one month [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=9478&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 two months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=9478&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) No exact matches found, but these alternatives could be just right ## Recommended hotels in Pittsfield ![Exterior](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/5740b713.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/83c805e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Berkshire Hills Inn & Suites [](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) 8.6/10 Excellent (1000) "Very friendly and good Breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jesse CA $106 CA $118 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/w6714h4455x8y0-7f30ce4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/dcc4e9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/b2a572bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/w4000h2467x0y0-95fb3171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) 9.4/10 Exceptional (73) "Very clean and friendly staff that go above and beyond for their guests even in a snow storm! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kira CA $170 CA $190 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/207845f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a97806ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) 8.0/10 Very good (1002) "Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa CA $136 CA $152 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/b6081d93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/d8f6f1fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/w696h390x1y0-dec65b39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/bba60f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Lenox Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information) 9.2/10 Wonderful (661) " Nice staff - beautiful hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARY CA $177 CA $198 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/77fe0507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/6761ce21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/465e60d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lodge in Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) 9.0/10 Wonderful (808) "great stall and friendly pet friendly place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) bonnie CA $137 CA $184 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/751d6e42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/b4275c3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Accessible](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/644deeee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/de2ab5d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel in Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Inn.h297173.Hotel-Information) 7.8/10 Good (841) "This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARIA J CA $112 CA $126 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Inn.h297173.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/c81c0732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/5a448032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Suite- NO PETS ALLOWED](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/e75ce45d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/0e28a2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Guesthouse in Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) 8.6/10 Excellent (353) "Very helpful staff, clean and spacious rooms. Has everything you need - well equipped." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn CA $130 CA $146 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/e57afaf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/e65bd9d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/3ef861f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel On North [](https://www.expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) 9.6/10 Exceptional (812) "Great staff, room was huge and comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cameron CA $206 CA $231 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/e1303f64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/411deb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/54590b16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/079bb1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information) CA $276 CA $458 total includes taxes & fees Jan 10 - Jan 11 [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/bdc7550f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/44aa4835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/3fc8dc3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/107000000/106660000/106650400/106650307/811d3663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) 7.8/10 Good (7) "The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Liz V. CA $373 CA $681 total includes taxes & fees Jan 10 - Jan 11 [](https://www.expedia.ca/Pittsfield-Hotels-3-Bedroom-Home-W-Lake-And-Mountain-Views-Near-Skiing.h106650307.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/5d0aa061.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/34fa691f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/ed3ffaa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89810000/89806300/89806253/w1440h1084x0y1-9f76bc91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Hancock [](https://www.expedia.ca/Pittsfield-Hotels-Hancock-Village-Inn-At-Jiminy-Peak.h89806253.Hotel-Information) 10/10 Exceptional (16) "Amazing Inn. Cozy and everything we needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Price F. CA $872 CA $1,592 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Pittsfield-Hotels-Hancock-Village-Inn-At-Jiminy-Peak.h89806253.Hotel-Information) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/abb5a87f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/c2037034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/1690062a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/3ed5d9ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel in Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.Hotel-Information) 5.4/10 (811) "Room spotless and staff helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $111 CA $124 total includes taxes & fees Jan 10 - Jan 11 [](https://www.expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/109000000/108500000/108496800/108496770/a1b50bde.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) ![Interior](https://images.trvl-media.com/lodging/109000000/108500000/108496800/108496770/4dc5b6f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108500000/108496800/108496770/6718b83f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-Chic-Corporate-Apartment-In-Wonderful-Pittsfield-With-AC.h108496770.Hotel-Information) 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 $187 CA $283 total includes taxes & fees Jan 10 - Jan 11 [](https://www.expedia.ca/Pittsfield-Hotels-Chic-Corporate-Apartment-In-Wonderful-Pittsfield-With-AC.h108496770.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/06dae0ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/3908437c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/251da7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element Lenox Berkshires [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) 9.6/10 Exceptional (15) "Spotless rooms and the friendliest service at the front desk! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $193 CA $215 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/e2e7e72f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/be126a14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/9ac40a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG [](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) 8.8/10 Excellent (716) "Nice warm pool and hot tub. Good little fitness center. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fawn CA $136 CA $152 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Private Bathroom (Clark - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/04b1723e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, Private Bathroom (Honeymoon - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/7ac0f2b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Private Bathroom (Garden - Pets Allowed) | Miscellaneous](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/c68ae4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bed & Breakfast in West Stockbridge [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) 9.6/10 Exceptional (440) "The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carin CA $151 CA $166 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/9aaa75ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/be4af91d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Cabin, 1 King Bed, Lake View](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/f1533622.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, 1 King Bed, Garden View](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/f581b284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Prospect Berkshires [](https://www.expedia.ca/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.Hotel-Information) 9.6/10 Exceptional (18) "Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $294 CA $375 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.Hotel-Information) ![Miscellaneous](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/e459ce18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/00c971b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/53f3f179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/6a32b13e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) 9.0/10 Wonderful (1003) "Room was clean and the staff was super friendly and helpful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ethan CA $135 CA $151 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/8679a614.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/c0f1d776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/7aabad6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/44727a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel in Williamstown [](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information) 9.2/10 Wonderful (889) "Excellent service and a beautifully decorated property." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ivana CA $96 CA $114 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gazebo](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/20495b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/17f29286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/7062b6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel in Lenox [](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) 7.6/10 Good (828) "Staff was very friendly and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela CA $109 CA $122 total includes taxes & fees Jan 10 - Jan 11 [](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.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=2026-01-23&endDate=2026-01-24®ionId=9478&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-11&d2=2026-04-11&lodging=CABIN) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-11&d2=2026-04-11&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-11&d2=2026-04-11&lodging=APARTMENT) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-11&d2=2026-04-11&lodging=VACATION_HOME) Condos [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-11&d2=2026-04-11&lodging=CONDO) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-11&d2=2026-04-11&lodging=COTTAGE) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-11&d2=2026-04-11&lodging=CHALET) Villas [](https://www.expedia.ca/Hotel-Search?destination=Pittsfield%2C+Massachusetts%2C+United+States+of+America®ionId=9478&latLong=42.44846%2C-73.253891&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-11&d2=2026-04-11&lodging=VILLA) ![](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-Villas.d9478-aaVillas.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Villas.d9478-aaVillas.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![Comfort Inn & Suites East Greenbush - Albany](https://images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/ea181a79_y.jpg) ### Comfort Inn & Suites East Greenbush - Albany 10/10 Excellent "The kids loved it!" [](https://expedia.ca/Albany-Hotels-Comfort-Inn-Suites-East-Greenbush-Albany.h1052319.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 "Extraordinary" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.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/e153ce9c_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "Very good " [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.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 "Absolutely fabulous!" [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "I've stayed here several times over the past two years. A real gem of a location, especially if you are staying several nights. " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.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 "Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Delicious sundae! Cozy fire!" [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Great staff, room was huge and comfortable. " [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Very pleasant and relaxing place to stay" [](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Villas information | Number of reviews | 14,557 | | ----------------- | -------- | | Accommodation | 3 Villas | | Lowest Price | CA $107 | | Highest Price | CA $231 | ## Frequently asked questions ### Why book your villa in Pittsfield with Expedia? ### How can I find cheap villas in Pittsfield? ### What is there to do near my villa in Pittsfield? ## 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) - 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