Title: Stockbridge Guest Houses from CA $139 | Expedia.ca [Stockbridge Travel Guide](https://expedia.ca/Stockbridge.dx162575)[Hotels in Stockbridge](https://expedia.ca/Stockbridge-Hotels.d162575.Travel-Guide-Hotels)[Vacation Rentals in Stockbridge](https://expedia.ca/Stockbridge-Vacation-Rentals.d162575.Travel-Guide-VacationRentals)[Flights to Stockbridge](https://expedia.ca/Cheap-Flights-To-Stockbridge.d162575.Travel-Guide-Flights)[Stockbridge Car Rentals](https://expedia.ca/Car-Rentals-In-Stockbridge.d162575.Car-Rental-Guide)[Stockbridge Vacation Packages](https://expedia.ca/Stockbridge.d162575.Destination-Travel-Guides) ![Linwood House at the Norman Rockwell Museum Stockbridge Massachusetts USA. Significant collection of the artist's original work & memorabilia on display in his hometown.](https://images.trvl-media.com/place/162575/de09378b-b417-4c3e-9c9a-1f58d65ad2fd.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by William Keller # Search Guest Houses in Stockbridge from CA $139 - ![](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 [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Stockbridge Guest Houses ![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) ![Exterior](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/4e933c7c.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) ![Terrace/patio](https://images.trvl-media.com/lodging/26000000/25810000/25808300/25808208/614a1cdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Village Carriage House - Super Private!! Lanesborough 9.8/10 Exceptional (268) "The cottage was amazing. Hope to be visit again and again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark M. CA $189 CA $295 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Lanesborough-Hotels-Berkshire-Village-Carriage-House.h25808208.Hotel-Information) ![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) ![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) ![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) ![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) ### The Central Downtown Inn & Suites Pittsfield 8.6/10 Excellent (346) "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 $125 CA $139 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.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) ![Interior](https://images.trvl-media.com/lodging/103000000/102470000/102462900/102462881/2567e987.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 (17) "Wonderful place - great location. Beautiful cottage and perfectly designed. Had everything we needed for a lone weekend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lauren P. CA $129 CA $451 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Hillsdale-Hotels-Hudson-Valley-And-The-Berkshires-Cottage.h102462881.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=2025-12-17&endDate=2025-12-18®ionId=162575&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_162575) ![](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%2FStockbridge-Guest-Houses.d162575-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FStockbridge-Guest-Houses.d162575-aaGuestHouses.Travel-Guide-Accommodation) ## Top Stockbridge Hotel Reviews ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Friendly staff, room was very clean. Pool area well maintained. Overall a great place to stay" [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "Great stay, great breakfast" [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "Clean room, staff friendliness, near store and amenities." [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.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 "Great service. Attentive staff. Great location. Rooms clean and comfortable. Thanks for another great stay! " [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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 "I visited Berkshire area for Thanksgiving and stayed at the brand new Holiday Inn Express. It was fantastic! The hotel is beautiful and pet friendly but also in a great location. The staff were amazing and professional. Over all 10/10 stay. Will definitely stay there again " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.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 "Everything was a great experience " [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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 "Great" [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.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 "Everything was great. " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Monument Mountain Motel](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94_y.jpg) ### Monument Mountain Motel 10/10 Excellent "Great place to stay! " [](https://expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) ## Find out more about Stockbridge ## Stockbridge Guest Houses information | Number of reviews | 629 | | --- | --- | | Accommodation | 10 Guest Houses | | Lowest Price | CA $139 | | Highest Price | CA $451 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Guest Houses in Alford](https://www.expedia.ca/Alford-Guest-Houses.d3000421226-aaGuestHouses.Travel-Guide-Accommodation) - [Alford Hotels](https://www.expedia.ca/Alford-Hotels.d3000421226.Travel-Guide-Hotels) - [Lodges in Alford](https://www.expedia.ca/Alford-Lodges.d3000421226-aaLodges.Travel-Guide-Accommodation) - [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) - 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