Title: Pittsfield Guest Houses from CA $155 | 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 Guest Houses in Pittsfield from CA $155 ![](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 [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=9478&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Pittsfield Guest Houses ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/fdeb3407.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/2000000/1460000/1457800/1457797/99b13181.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/d28e6aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe King Interior Suite- NO PETS ALLOWED](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/88509527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Central Downtown Inn & Suites Pittsfield 8.8/10 Excellent (323) "Nice place " CA $138 CA $155 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) ![Romantic Room, 1 King Bed (Room 4)](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/219287f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch LCD TV with digital channels, printers](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/0a4a8480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Room, 1 King Bed (Room 4)](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/674accb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/20208a7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Revival House Adams 8.8/10 Excellent (19) "We thoroughly enjoyed our stay at The Revival House! Super comfortable, clean, and the inside has great decor sensibilities. We will be back if we’re ever in the area again!" CA $244 CA $272 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Adams-Hotels-The-Revival-House.h113486763.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/afbb4318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/9becd207.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/4e933c7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/8c4366ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Village Carriage House - Super Private!! Lanesborough 9.8/10 Exceptional (261) "We enjoyed our stay. Excellent location to explore Western Mass!" CA $210 CA $321 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102470000/102462900/102462881/1ecb675b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102470000/102462900/102462881/ca444bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/103000000/102470000/102462900/102462881/5ec352f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/103000000/102470000/102462900/102462881/7c480e6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hudson valley and The Berkshires Cottage Hillsdale 10/10 Exceptional (15) "We had a great weekend stay at The Cottage. We loved the accommodations- great decor! Very clean and comfortable accommodations. Will definitely come back!" CA $92 CA $408 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Hillsdale-Hotels-Hudson-Valley-And-The-Berkshires-Cottage.h102462881.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/6000000/5210000/5203000/5202927/7aa060b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Deluxe King](https://images.trvl-media.com/lodging/6000000/5210000/5203000/5202927/ed603c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Birchwood Suite](https://images.trvl-media.com/lodging/6000000/5210000/5203000/5202927/ded30af4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/6000000/5210000/5203000/5202927/4d651e83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Dewey Lenox 8.8/10 Excellent (325) "Great spot. Lots of history. " CA $197 CA $221 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Lenox-Hotels-The-Dewey.h5202927.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=2025-10-26&endDate=2025-10-27®ionId=9478&adults=2&lodging=GUEST_HOUSE&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-Guest-Houses.d9478-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FPittsfield-Guest-Houses.d9478-aaGuestHouses.Travel-Guide-Accommodation) ## Top Pittsfield Hotel Reviews ![Hotel On North](//images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "We greatly enjoyed our weekend at the Hotel. The lobby decor and welcoming staff got us off on the right foot. 👌Our room was spacious and clean. The gift shop had some great finds, and the restaurant featured great food and excellent service. We would definitely stay here again for our next trip to the Berkshires!" [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.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 "Super friendly staff, a free coffee bar in the lobby, loads of food and shopping options within walking distance, free on-site parking - what’s not to love! And the room was spotlessly clean and very very comfortable. We love this place!!!" [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.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 "Staff very friendlt" [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Easy parking, great community spaces, beautiful decor! " [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Great lodge with 1 bedroom suites and fully stocked kitchens " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Vacation Village in the Berkshires](//images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Clean room. Spacious with lovely things to do. " [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "Clean venue. Very quiet and I highly recommend renting a kayak. You might see a bald eagle:)" [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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 "This is a fun family resort... a great vacation place .. in a great location.. something for everyone. Perfect family reunion place.. All Ages happy.. " [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![The Williams Inn](//images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Nice place to stay for a wedding " [](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ## Find out more about Pittsfield ## Pittsfield Guest Houses information | Number of reviews | 807 | | --- | --- | | Accommodation | 10 Guest Houses | | Lowest Price | CA $155 | | Highest Price | CA $408 | ## 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) - 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[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 Guest Houses in Pittsfield on Expedia.com](https://www.expedia.com/Pittsfield-Guest-Houses.d9478-aaGuestHouses.Travel-Guide-Accommodation)