Great Barrington: Vacation Rental By Owner

Showing 20 Of 46 Vacation Rentals
  • Property-1 Image 1
    House $329 / Nightly
    • 2 Bed
    • 1 Baths
    • (34)
    Great Barrington, MA

    Nestled on the outskirts of Housatonic, a village in Great Barrington,MA. Country living at its best. Just minutes away from historic down town Great Barrington... ...more

  • Property-2 Image 1
    House $926 / Nightly
    • 7 Bed
    • 5 Baths
    • (16) Exceptional
    Great Barrington, MA

    This is a unique property located on more then 1000 feet of the Green River, one of the best Trout rivers in MA. Over a hundred and sixty acres of beautiful woods... ...more

  • Property-3 Image 1
    House $524 / Nightly
    • 5 Bed
    • 3 Baths
    • (1) Exceptional
    Great Barrington, MA

    This home is the perfect answer to fit your vacationing needs at any time of year. Ski, snowboard, snowshoe, or other outdoor activities in the Winter. Attend... ...more

  • Property-4 Image 1
    House Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (1) Exceptional
    Great Barrington, MA

    This tranquil getaway is miles away from stress and hustle but just minutes' walk from the amazing shopping, dining and culture of Main Street Great Barrington.... ...more

  • Property-5 Image 1
    Cottage $293 / Nightly
    • 1 Bed
    • 1 Baths
    • (8) Exceptional
    Great Barrington, MA

    There is only one cottage--30' away from our home--on this three-acre property. It has its own entrance and its own parking space. The pool is shared with us,... ...more

  • Property-6 Image 1
    House $456 / Nightly
    • 4 Bed
    • 2 Baths
    • (5)
    Great Barrington, MA

    Leave your busy schedule behind for a life of leisure at this vacation rental hideaway. This 4-bedroom, 2-bath home is complete with woodsy-style decor,... ...more

  • Property-7 Image 1
    Cottage $270 / Nightly
    • 2 Bed
    • 1 Baths
    • (63) Wonderful
    Great Barrington, MA

    NOW THROUGH MAY 10th 2020 - 2k/30 days!! Welcome to our Schoolhouse located in the heart of the Berkshires. Set in front of the ledges of Warner Mountain,... ...more

  • Property-8 Image 1
    Farmhouse $433 / Nightly
    • 3 Bed
    • 1 Baths
    • (25)
    Great Barrington, MA

    Ideal location on ‘’The Hill’’ in the heart of Great Barrington. Walk to Lake Mansfield and the center of town. This lovely 3 bedroom farmhouse is situated in a... ...more

  • Property-9 Image 1
    Apartment $292 / Nightly
    • 2 Bed
    • 1 Baths
    • (5) Exceptional
    Great Barrington, MA

    This 1000 square foot apartment offers a place for friends and family to spread out and make the stay comfortable. In the kitchen you will find an arrangement of... ...more

  • Property-10 Image 1
    House $209 / Nightly
    • 4 Bed
    • 2 Baths
    • (15) Wonderful
    Great Barrington, MA

    Renovated historic cape in the center of the quiet village of Housatonic. Five bedrooms, six beds, two full baths, private fenced backyard with hot tub and... ...more

  • Property-11 Image 1
    Cottage $339 / Nightly
    • (2) Excellent
    Great Barrington, MA

    The Cottage at Windflower Inn - close to skiing, shopping, hiking, and the arts. Located towards the back of the Windflower Inn property, our rental cottage... ...more

  • Property-12 Image 1
    House $583 / Nightly
    • 4 Bed
    • 3 Baths
    • (7) Exceptional
    Great Barrington, MA

    High-end, fully furnished, beautiful contemporary home on a private, four-acre, wooded estate next to Butternut Mountain. An open, three-level floorplan, tons of... ...more

  • Property-13 Image 1
    House $462 / Nightly
    • 4 Bed
    • 3 Baths
    • (17) Wonderful
    Great Barrington, MA

    Built in 2015, this lovely 4 bedroom, 2500 sq.ft. home on a knoll is set back 175 feet from the street. This charming home offers privacy and flexibility for... ...more

  • Property-14 Image 1
    House $369 / Nightly
    • 4 Bed
    • 3 Baths
    • (2) Very Good
    Great Barrington, MA

    SPECIAL PRICING AVAILABLE FOR SKI SEASON; PLEASE INQUIRE. Spacious house in excellent condition on 3 secluded acres in Great Barrington, the heart of the... ...more

  • Property-15 Image 1
    House $480 / Nightly
    • 4 Bed
    • 3 Baths
    • (14) Wonderful
    Great Barrington, MA

    Enjoy our newly renovated haven (all new appliances, furniture, linens and towels) in the relaxing yet vibrant town of Great Barrington. We're just minutes from... ...more

  • Property-16 Image 1
    Cabin $2,184 / Nightly
    • 5 Bed
    • 7 Baths
    • (23) Exceptional
    Great Barrington, MA

    7,500 SQ.FT. log cabin The perfect getaway on 10+ private acres. Once you're inside, you won't want to leave. CHECK IN SUPER EARLY AND CHECK OUT LATE - WE WANT... ...more

  • Property-17 Image 1
    House $184 / Nightly
    • 2 Bed
    • 1 Baths
    • (24)
    Great Barrington, MA

    A short drive from New York City or Boston, or a flight into Hartford or Albany and you're in a new world of peacefulness - Gemini's Place in the Berkshires.... ...more

  • Property-18 Image 1
    House Select Dates for Price
    • 4 Bed
    • 3 Baths
    Great Barrington, MA

    Situated on "The Hill" in Great Barrington, our beautiful modern Victorian home is just minutes from Main Street and Lake Mansfield. Our house is contemporary,... ...more

  • Property-19 Image 1
    House $815 / Nightly
    • 5 Bed
    • 5 Baths
    • (18) Exceptional
    Great Barrington, MA

    Located in the beautiful Berkshires, MA, the 5000 sqf home is located in a desired neighborhood known as "the Hill.” The sun filled house is on a quiet no outlet... ...more

  • Property-20 Image 1
    House $2,318 / Nightly
    • 6 Bed
    • 7 Baths
    • (2) Exceptional
    Great Barrington, MA

    This fabulous Timberframe Home has the best of all worlds for your family to enjoy time in the Berkshires. The panoramic views are breathtaking. A very private... ...more

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Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Great Barrington. Many accommodations in Great Barrington provide "Non Smoking Only", there are 77, or there are 65 of Vacation Rentals in Great Barrington with a "Children Welcome", there are also 61 with "Biking", which is another great reason to visit Great Barrington.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Great Barrington. The most expensive month of the next 12 months is in June, where prices hit an average of $656 a night. In July, prices will hit an average low of $509 per night.