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Holiday Rentals near Housatonic River Walk

195 Main St, Great Barrington, Massachusetts 01230-1602
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    Travellers to Great Barrington are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    All 37 Rentals in Great Barrington
    Lakefront Berkshires Ski/Summer House, Great Views1 / 17
    (4)Very good
    6.2 kilometres from Housatonic River Walk
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Berkshires: Romantic Cottage with spectacular view1 / 18
    (24)Excellent
    3.5 kilometres from Housatonic River Walk
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Gem of the Berkshires, walk to downtown & lake.1 / 30
    (4)Excellent
    0.5 kilometres from Housatonic River Walk
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Shaker Hill1 / 27
    (2)Average
    6.8 kilometres from Housatonic River Walk
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Porch
    • Grill
    • Wi-Fi
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    • Mountain Views
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 September 2014
    This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
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    About this property
    Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fields, diverse wetlands,...
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    Great Barrington, Berkshires
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Eco-friendly cozy home in Gt. Barrington1 / 14
    (1)Very good
    2.7 kilometres from Housatonic River Walk
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There are about twelve (12!) hiking...
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    Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    2.7 kilometres from Housatonic River Walk
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    About this property
    In 2016 Smithsonian Magazine deemed Great Barrington, 'The Best Small Town in America.' Manor Lane is a private French Country Estate located only 5 minutes from the heart of the Berkshires. Situated 10 minutes to both Butternut and Catamount ski mountains and 25 minutes to Tanglewood. Manor Lane...
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    1.1 kilometres from Housatonic River Walk
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    This updated home has a luxurious feel! Close proximity to downtown Great Barrington is convenient and allows for easy access to the world's cultural epicenter. Located on a dirt road in a gentle neighborhood. About 1/2 mile from Lake Mansfield. Dehon road cuts over to the lake! The upgraded...
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    4.3 kilometres from Housatonic River Walk
    7 Bedrooms, 8 Bathrooms, Sleeps 15 Quick View
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    About this property
    This charming former tavern and stage coach inn makes the perfect 4 season getaway for large group gatherings, family reunions, weddings or any occasion. Enjoy everything the Berkshires has to offer from the shops and restaurants in Great Barrington, skiing at Butternut Ski resort, and music and...
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    Great Barrington, Berkshires
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 15
    Beautiful 1920's Colonial 20 Minutes from Tanglewood1 / 16
    (51)Excellent
    3.0 kilometres from Housatonic River Walk
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    HOT TUB, FIREPLACE, BEAUTIFUL, COMFORTABLE, WALK TO RESTAURANTS, WEEKEND RATES!1 / 24
    (12)Excellent
    0.8 kilometres from Housatonic River Walk
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Berkshires, Ma. Close to Tanglewood, Jacob's PIllow, Berkshire Theater1 / 13
    (8)Excellent
    1.2 kilometres from Housatonic River Walk
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    A Beautiful Cabin In The Heart Of The Berkshires1 / 25
    (12)Excellent
    5.9 kilometres from Housatonic River Walk
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    4.7 kilometres from Housatonic River Walk
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    COZY LOG HOME* fireplace, skiing,fall foliage Hiking, Berkshires*1 / 24
    (37)Excellent
    4.0 kilometres from Housatonic River Walk
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Washer
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    Great Barrington, Berkshires
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
    Sold out for the summer.    Booking for fall, winter &  all '21! Room for 12!1 / 29
    (48)Excellent
    2.7 kilometres from Housatonic River Walk
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Patio
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Great Barrington, Berkshires
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Great Barrington - The Cottage at Windflower Inn - Low Price - Close to Skiing1 / 11
    (2)Very good
    5.1 kilometres from Housatonic River Walk
    Studio, 3 Bathrooms, Sleeps 9 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 3 Bathrooms, Sleeps 9
    Great Barrington Retreat ! Booking for the Fall Now!1 / 38
    (49)Excellent
    1.2 kilometres from Housatonic River Walk
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Stunning Renovated Victorian1 / 50
    (16)Excellent
    1.0 kilometres from Housatonic River Walk
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Rustic modern house in Great Barrington near town, lake, Tanglewood and ski!1 / 22
    (3)Excellent
    3.1 kilometres from Housatonic River Walk
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Modern Victorian on the Hill1 / 37
    (1)Excellent
    0.5 kilometres from Housatonic River Walk
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Charming, Newly Renovated Home Close to All Berkshire Attractions1 / 11
    (14)Excellent
    4.3 kilometres from Housatonic River Walk
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    0.5 kilometres from Housatonic River Walk
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Beautiful Berkshire Farm House on 160+ Acres1 / 32
    (16)Excellent
    8.4 kilometres from Housatonic River Walk
    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 16
    Downtown GB apartment walk to shops and restaurants1 / 20
    (14)Excellent
    0.4 kilometres from Housatonic River Walk
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Great Barrington, Berkshires
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Magnificent views, walk to Lake Mansfield!1 / 35
    (1)Excellent
    0.3 kilometres from Housatonic River Walk
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    3.0 kilometres from Housatonic River Walk
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Upscale Country Cottage1 / 21
    (1)Excellent
    5.2 kilometres from Housatonic River Walk
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Barn Apartment in Gorgeous Stonybrook Farm1 / 13
    (3)Very good
    4.3 kilometres from Housatonic River Walk
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Great Barrington, Berkshires
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Lake Community - Near Town, Attractions -  2020 MA Residents Only1 / 17
    (24)Excellent
    7.5 kilometres from Housatonic River Walk
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Waterfront Cottage - 10 Mins to Great Barrington!1 / 24
    (4)Excellent
    7.3 kilometres from Housatonic River Walk
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 30 June 2018
    We had an excellent time with our two kids (7 and 8). The house is right on the lake with a great deck and amazing views. We used the kayaks every day. Location was great...
    Reviewed 22 June 2018
    Perfect location, perfect weather, beautiful view! Excellent owner, Carol, who responded to all our questions immediately. Would go back again in a minute.
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    About this property
    Let this serene lakefront Great Barrington area cottage in New Marlborough serve as your ultimate home-away-from-home! Featuring 2 bedrooms, 1-bathroom, and enough room to sleep 4 guests, this year-round vacation rental cottage is sure to give you an experience in the Berkshires that you will never...
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    New Marlborough, Berkshires
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    7.3 kilometres from Housatonic River Walk
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Located along the Appalachian trail and 3 miles to Great Barrington, this designer home is central to all the Berkshires has to offer, not to mention being 35 minutes to Hudson you are really in the center of of it all. This completely separate designer home is located on the 2nd and 3rd floors...
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    Sheffield, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Newly Renovated Colonial on the River! Sleeps 5-61 / 20
    (1)Excellent
    7.7 kilometres from Housatonic River Walk
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    Blue House on the Bend Newly renovated historic eyebrow colonial located on an idyllic bend of the Housatonic river comfortably accommodates 5 or 6 people. Built around 1820, the Blue House on the Bend has been updated and outfitted for modern day convenience but retains its charm and unique...
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    Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    7.3 kilometres from Housatonic River Walk
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Bring your loved one or best friend along on a Berkshires getaway in this 1-bedroom, 1-bath vacation rental in New Marlborough. Nestled just 30 yards from private right-of-way access to Lake Buel, this cabin offers unbeatable views of the lake and the Berkshire Mountains. Launch the 2 new kayaks,...
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    New Marlborough, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    6.8 kilometres from Housatonic River Walk
    Studio, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    You'll love our hand-hewn post & beam beauty on 13 acres in the Berkshire Mountains of Western Mass located near the Monterey/Great Barrington line, close to everything. Great for summer and winter ski season. Rich in both outdoor and cultural attractions, shopping and antiquing. Located adjacent...
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    Monterey, Berkshires
    Holiday Rental House - 2 Bathrooms, Sleeps 7
    7.5 kilometres from Housatonic River Walk
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Housekeeping Included
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    About this property
    We offer two bedrooms accessible via a private staircase in our recently renovated Victorian farm house located on two beautifully landscaped acres with seasonal gardens and adjoining woods and fields. Each bedroom sleeps 2; they can be booked individually or together at $105/bedroom/night. We...
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    West Stockbridge, Berkshires
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Lakefront Berkshires Retreat w/ Deck, Dock & Boat!1 / 26
    (1)Average
    6.5 kilometres from Housatonic River Walk
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 September 2019
    My family liked the decor, had space to sleep with all our kids, and was close to great small towns in the Berkshires. The house was clean, had plenty of hot water and laundry...
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    About this property
    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, contemporary furnishings, and space for 10. It's truly a sportsman's paradise - tucked away in the woods on Round Pond, where you can hike, fish,...
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    Housatonic, Berkshires
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    7.3 kilometres from Housatonic River Walk
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    With 150 feet of lakefront property on Lake Buel - a pristine 192-acre mountain lake - this lovely 3-bedroom, 2.5-bath home is sure to be the perfect 3-season getaway. Enjoy sitting on the deck to take in the water views, gathering around the fire pit to roast s’mores, or fishing right off the...
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    Location Information
    Monterey, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    $AUD
    Australia

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