Title: Book the Best BOUTIQUE Hotels in Stockbridge in 2025 | 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) ![](https://mediaim.expedia.com/destination/1/5c9675f1022a9d16db477be7ba7a1dae.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Boutique Hotels in Stockbridge, MA from CA $106 ![](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 availability on Stockbridge Boutique Hotels Tonight [Oct 9 - Oct 10](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2025-10-09&endDate=2025-10-10&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 10 - Oct 11](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2025-10-10&endDate=2025-10-11&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2025-10-10&endDate=2025-10-12&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=162575&startDate=2025-10-17&endDate=2025-10-19&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Stockbridge Boutique Hotels We don't have any properties that match your exact search [See all properties in Stockbridge](https://expedia.ca/Hotel-Search?startDate=2025-10-24&endDate=2025-10-25®ionId=162575&adults=2) ## Recommended hotels in Stockbridge ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds (Main Inn)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/5f2e6b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Firehouse)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/71ef2331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Main Inn Queen)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/3ac2703b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn Stockbridge 8.8/10 Excellent (1007) "great place have stayed several times, and hope to return." CA $197 CA $283 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Business centre](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/587b0e23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (RedBird Suite) | View from room](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ceeb05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/2e09a8f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (RedBird Suite)](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ab46e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood Stockbridge 9.2/10 Wonderful (105) "Great breakfast, friendly helpful staff, pretty yard, good location " CA $434 CA $525 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/4a1ad790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Untold Lenox 9.0/10 Wonderful (752) "Easy parking, great community spaces, beautiful decor! " CA $123 CA $137 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/137f5231.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/3f004a6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Tent](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/e9560cda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/2b2e1d76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Huttopia Berkshires Williamstown 10/10 Exceptional (4) "Perfect place for a relaxing getaway! We loved everything! " CA $137 CA $153 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Non Lakeside Superior Room, 2 Queen beds](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/d3eea453.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/ba9d3ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel Lee 9.0/10 Wonderful (1006) "Great Indian restaurant in the hotel!" CA $149 CA $166 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/126ab2c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/bf0ac5a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/4d496801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free continental breakfast](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/29fdf381.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Travel Lodge Austerlitz 5.4/10 (448) "The motel seems to be managed and cleaned by the owners. Not the ritz, but clean and a bargain compared with other lodging in the area. The owner was very responsive. " CA $95 CA $106 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Albany-Hotels-Berkshire-Travel-Lodge.h1793522.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/69831a98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 3 Bedrooms, Mountainside | Living area](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/2f0dc604_edited_9c5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free continental breakfast on weekends](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/d5a67b67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Suite, 1 King Bed, Patio | Living area](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/d7f7feed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Springs Motel New Ashford 9.2/10 Wonderful (74) "The Springs Motel was a delight! Something away from the boring, staple type of hotel. The staff was so friendly and welcoming. The coffee and breakfast is a great touch! Can't wait to go back" CA $141 CA $155 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/New-Ashford-Hotels-The-Springs-Motel.h95124564.Hotel-Information) ![Library](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/50a90cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/d4318cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/e7ac793d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/52bc8d96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blackberry River Inn Norfolk 9.4/10 Exceptional (142) "Loved everything especially Lucas and Joe💟☮️" CA $229 CA $264 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Norfolk-Hotels-Blackberry-River-Inn.h95991149.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) ![Dining](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/3ef861f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/651f878e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/9e766351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel On North Pittsfield 9.6/10 Exceptional (778) "Great property! Very large clean room in a unique hotel! " CA $154 CA $172 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/b5e2455f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/9aabb83a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/a831aba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Lee 8.4/10 Very good (1005) "Staff was very helpful - easy location - clean rooms!" CA $130 CA $145 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Lee-Hotels-Quality-Inn.h459706.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=2025-10-24&endDate=2025-10-25®ionId=162575&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top Stockbridge Hotel Reviews ![Hotel On North](//images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "There was construction noise next door." [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ## Frequently asked questions ### What's there to see and do in Stockbridge? > The bars and historic landmarks are just some of the things to enjoy while you're in the area. Activities and attractions to experience around Stockbridge include Naumkeag Museum, Norman Rockwell Museum, and Frelinghuysen Morris House and Studio. For even more to see and do, make a stop at National Shrine of the Divine Mercy, Berkshire Botanical Garden, and Housatonic River. ### What kind of weather should I plan for when I travel to Stockbridge? > Having a good idea of the weather in Stockbridge will help you enjoy your stay to the fullest. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall. ### What's the best way to get to my boutique hotel in Stockbridge? > You have a few options for getting to and around Stockbridge. The nearest major airport is Pittsfield, MA (PSF-Pittsfield Municipal), which is located 9.6 mi (15.5 km) from the heart of the city, but Hudson, NY (HCC-Columbia County) may also be an option. 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