Title: Great Barrington Cottages from CA $449 | Expedia.ca [Great Barrington Travel Guide](https://expedia.ca/Great-Barrington.dx110336)[Hotels in Great Barrington](https://expedia.ca/Great-Barrington-Hotels.d110336.Travel-Guide-Hotels)[Vacation Rentals in Great Barrington](https://expedia.ca/Great-Barrington-Vacation-Rentals.d110336.Travel-Guide-VacationRentals)[Flights to Great Barrington](https://expedia.ca/Cheap-Flights-To-Great-Barrington.d110336.Travel-Guide-Flights)[Great Barrington Car Rentals](https://expedia.ca/Car-Rentals-In-Great-Barrington.d110336.Car-Rental-Guide)[Great Barrington Vacation Packages](https://expedia.ca/Great-Barrington.d110336.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/110336/4c3d827f-8ba1-4754-a7a1-6fe14b81f0f7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/110336/4c3d827f-8ba1-4754-a7a1-6fe14b81f0f7.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 - 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Aug 2](https://www.expedia.ca/Hotel-Search?regionId=110336&startDate=2026-07-31&endDate=2026-08-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Great Barrington cottages ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/8b8ec1dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/4cd10809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/4d94624e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/c0b1b1ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck [](https://www.expedia.ca/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.Hotel-Information) Stephentown CA $273 CA $770 total includes taxes & fees Apr 8 - Apr 9 [](https://www.expedia.ca/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658954/2aadb8b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658954/43404c2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658954/55508efd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120660000/120659000/120658954/2f269d95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet-Friendly Hudson Escape w/ Hot Tub [](https://www.expedia.ca/Hudson-Hotels-Pet-Friendly-Hudson-Escape-W-Hot-Tub.h120658954.Hotel-Information) Stottville CA $250 CA $449 total includes taxes & fees Apr 28 - Apr 29 [](https://www.expedia.ca/Hudson-Hotels-Pet-Friendly-Hudson-Escape-W-Hot-Tub.h120658954.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99410000/99407400/99407400/856cedc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![15 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99410000/99407400/99407400/ca2ed981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99410000/99407400/99407400/2cd54c4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/100000000/99410000/99407400/99407400/caa0ad88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires farm, 30+ guests, 50 acres [](https://www.expedia.ca/New-Lebanon-Hotels-Berkshires-Farm.h99407400.Hotel-Information) New Lebanon 10/10 Exceptional (1 review) CA $1,369 CA $2,573 total includes taxes & fees May 6 - May 7 [](https://www.expedia.ca/New-Lebanon-Hotels-Berkshires-Farm.h99407400.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=2026-04-21&endDate=2026-04-22®ionId=110336&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Great+Barrington%2C+Massachusetts%2C+United+States+of+America®ionId=110336&latLong=42.19598%2C-73.362007&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=VACATION_HOME) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Great+Barrington%2C+Massachusetts%2C+United+States+of+America®ionId=110336&latLong=42.19598%2C-73.362007&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Great+Barrington%2C+Massachusetts%2C+United+States+of+America®ionId=110336&latLong=42.19598%2C-73.362007&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=COTTAGE) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Great+Barrington%2C+Massachusetts%2C+United+States+of+America®ionId=110336&latLong=42.19598%2C-73.362007&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Great+Barrington%2C+Massachusetts%2C+United+States+of+America®ionId=110336&latLong=42.19598%2C-73.362007&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=APARTMENT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Great+Barrington%2C+Massachusetts%2C+United+States+of+America®ionId=110336&latLong=42.19598%2C-73.362007&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Great+Barrington%2C+Massachusetts%2C+United+States+of+America®ionId=110336&latLong=42.19598%2C-73.362007&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=VILLA) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Great+Barrington%2C+Massachusetts%2C+United+States+of+America®ionId=110336&latLong=42.19598%2C-73.362007&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=CHALET) ![](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%2FGreat-Barrington-Cottages.d110336-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FGreat-Barrington-Cottages.d110336-aaCottages.Travel-Guide-Accommodation) ## Top Great Barrington Hotel Reviews ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb_y.jpg) ### Berkshires Untold 10/10 Excellent "Unique and charming property. Super clean and staff are welcoming . If you are visiting this beautiful area of the Berkshires, it’s a great place to stay! " [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Travelodge by Wyndham Great Barrington Berkshires](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51_y.jpg) ### Travelodge by Wyndham Great Barrington Berkshires 10/10 Excellent "Clean" [](https://expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) ![Quality Inn Great Barrington](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/ed6ed4e8_y.jpg) ### Quality Inn Great Barrington 8/10 Good "Room and bed were clean as I would expect bath and toilet were clean, shower pressure was mediocre as I usually expect. Location was excellent as my ski resorts were within close proximity as well as restaurants (think Bogies, awesome food and reasonable prices). Check in was a breeze and Brian the manager was quite pleasant and informative. Will stay again on my next ski trip in the area." [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Love that place. Does need a little sprucing up. Staff great and accomodating " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Monument Mountain Motel](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/220f6cfe_y.jpg) ### Monument Mountain Motel 8/10 Good "Very clean and cozy in a great location! " [](https://expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.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 6/10 Okay "Great dinner, nice room. Only complaint is that none of the 3 elevators would come to the 6 floor in the morning. It was a long walk with our baggage." [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![The Berkshire Mountain Inn](https://images.trvl-media.com/lodging/126000000/125350000/125340300/125340225/b3935f27_y.jpg) ### The Berkshire Mountain Inn 10/10 Excellent "We had a lovely stay at the inn— Curry is a friendly, helpful innkeeper and couldn’t have been kinder! The room was spotless and spacious with a comfortable bed, and a lovely continental breakfast was provided. The short walk or drive to the charming downtown of Great Barrington made it even nicer! Highly recommend!" [](https://expedia.ca/Great-Barrington-Hotels-The-Berkshire-Mountain-Inn.h125340225.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/6897a130_y.jpg) ### The Red Lion Inn 10/10 Excellent "What a beautiful, unique building. Full of antiques and feels like going back in time. The ride up to my fourth floor room in the 19th century cage elevator was a wonderful touch. Can’t wait to go back again. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 8/10 Good "Room temperature was good. Breakfast coukd improve, lack of protein, muffins were not fresh. " [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ## Find out more about Great Barrington ## Great Barrington Cottages information | Number of reviews | | | ----------------- | ------------ | | Accommodation | 131 Cottages | | Lowest Price | CA $449 | | Highest Price | CA $2,573 | ## Frequently asked questions ### How much do cottages in Great Barrington cost? ### How many cottages are there in Great Barrington? ### Why book your cottage in Great Barrington with Expedia? ### How can I find cheap cottages in Great Barrington? ### What is there to do in Great Barrington near my cottage? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [3 Star Hotels in Stockbridge ](https://www.expedia.ca/3Star-Stockbridge-Hotels.s30-0-d162575.Travel-Guide-Filter-Hotels) - [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) - 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