Title: West Stockbridge Guest Houses from CA $165 | Expedia.ca [Hotels in West Stockbridge](https://expedia.ca/West-Stockbridge-Hotels.d173346.Travel-Guide-Hotels)[Vacation Rentals in West Stockbridge](https://expedia.ca/West-Stockbridge-Vacation-Rentals.d173346.Travel-Guide-VacationRentals)[Flights to West Stockbridge](https://expedia.ca/Cheap-Flights-To-West-Stockbridge.d173346.Travel-Guide-Flights)[West Stockbridge Car Rentals](https://expedia.ca/Car-Rentals-In-West-Stockbridge.d173346.Car-Rental-Guide)[West Stockbridge Vacation Packages](https://expedia.ca/West-Stockbridge.d173346.Destination-Travel-Guides) ![Olivias Overlook - West Stockbridge, Massachusetts](https://images.trvl-media.com/place/173346/8a572978-a908-43ba-b1f1-0a856c5003da.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/173346/8a572978-a908-43ba-b1f1-0a856c5003da.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=173346&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=173346&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=173346&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=173346&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for West Stockbridge guest houses ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/4092a889.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/d652d2fd.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) ### The Central Downtown Inn & Suites [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) Pittsfield 8.6/10 Excellent (355 reviews) "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 $148 CA $165 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/614a1cdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/9ad8b813.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/0ab1624d.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) ### Berkshire Village Carriage House - Super Private!! [](https://www.expedia.ca/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.Hotel-Information) Lanesborough 9.8/10 Exceptional (273 reviews) "It was a cute property- just what we needed. Nice location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda M. CA $183 CA $283 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.Hotel-Information) ![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/103000000/102470000/102462900/102462881/761b9b0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102470000/102462900/102462881/ad389e9e.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 [](https://www.expedia.ca/Hillsdale-Hotels-Hudson-Valley-And-The-Berkshires-Cottage.h102462881.Hotel-Information) Hillsdale 10/10 Exceptional (17 reviews) "Very clean and great for a couples trip!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sean C. CA $161 CA $476 total includes taxes & fees Mar 10 - Mar 11 [](https://www.expedia.ca/Hillsdale-Hotels-Hudson-Valley-And-The-Berkshires-Cottage.h102462881.Hotel-Information) ![The Garden Suite](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/8d4ea02b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Parlor Suite | Living area](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/fe8573a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/0b5f32ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Parlor Suite](https://images.trvl-media.com/lodging/103000000/102690000/102681000/102680999/49347d3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 9 Academy [](https://www.expedia.ca/Salisbury-Hotels-9-Academy.h102680999.Hotel-Information) Salisbury 9.0/10 Wonderful (10 reviews) "Nice room. " ![South Korea](https://a.travel-assets.com/egds/marks/flags/kr.svg) JeongHoon CA $644 CA $741 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Salisbury-Hotels-9-Academy.h102680999.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=2026-02-25&endDate=2026-02-26®ionId=173346&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_173346) ![](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%2FWest-Stockbridge-Guest-Houses.d173346-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWest-Stockbridge-Guest-Houses.d173346-aaGuestHouses.Travel-Guide-Accommodation) ## Top West Stockbridge Hotel Reviews ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Room was spotless, staff was amazing! Loved the bathroom setup! Will recommend and stay again! " [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "Clean room, nice staff , decent breakfast. Overall a good stay . " [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Only stayed for 1 night but was very impressed with this property. The room was very clean and spacious. Bed was comfortable as well. Had my two kids with me so the pool and hot tub was an amazing amenity. Left early in the morning to ski so the stay was short, but would’ve loved to stay longer and will definitely look to return to this property in the future. " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "The staff is very helpful, and always willing to assist with any inquiries. The room was definitely clean and well-stocked throughout our entire stay." [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Shaker Mill Inn](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57_y.jpg) ### Shaker Mill Inn 10/10 Excellent "Had everything we needed. Very thoughtful touches. " [](https://expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Spacious 2 bed 2 bath!" [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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 "Rooms were clean and spacious. Our room had 2 queen beds and they easily accommodated 2 of us and our late teen children. It's only 20 minutes from Jiminy Peak skiing area. There are several breakfast and food places nearby. " [](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 "loved " [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "The staff was very nice. The breakfast very good. Comfortable bed. Adjustable temperature." [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ## Find out more about West Stockbridge ## West Stockbridge Guest Houses information | Number of reviews | 655 | | ----------------- | --------------- | | Accommodation | 11 Guest Houses | | Lowest Price | CA $165 | | Highest Price | CA $741 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [3 Star Hotels in Stockbridge ](https://www.expedia.ca/3Star-Stockbridge-Hotels.s30-0-d162575.Travel-Guide-Filter-Hotels) - [Alford Hotels ](https://www.expedia.ca/Alford-Hotels.d3000421226.Travel-Guide-Hotels) - [Hotels near Berkshire Botanical Garden ](https://www.expedia.ca/Berkshire-Botanical-Garden-Hotels.0-l553248621532665247-0.Travel-Guide-Filter-Hotels) - [Hotels near Chesterwood ](https://www.expedia.ca/Chesterwood-Hotels.0-l6091841-0.Travel-Guide-Filter-Hotels) - [Farmstay in Glendale ](https://www.expedia.ca/Glendale-Agritourism.d901769277689110528-aaAgritourism.Travel-Guide-Accommodation) - 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