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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 May dates now. Secure your holiday rental today, and have the perfect trip.
    All 14 Rentals in Great Barrington
    Lakefront Berkshires Ski/Summer House, Great Views1 / 34
    (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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    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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    Amenities & Details
    • Parking
    • Private Garden
    • Porch
    • Outdoor Dining Area
    • Washer
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Amenities & Details
    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Waterfront Cottage - 10 Mins to Great Barrington!1 / 24
    (4)Excellent
    7.3 kilometres from Housatonic River Walk
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Central Heating
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Waterfront
    • Patio
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 plenty of room, this year-round vacation rental cottage is sure to give you an experience in the Berkshires that you will never forget! Go...
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    Monterey, Berkshires
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 2
    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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    Amenities & Details
    • Internet Access
    • Patio
    • Waterfront
    • Central Heating
    • Cable/satellite TV
    • Porch
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rustic Berkshires Cottage at Lake Buel w/ Kayaks!1 / 24
    (1)Excellent
    7.3 kilometres from Housatonic River Walk
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 September 2020
    The Miown Cabin was the perfect place for me to get away from the stresses of the Covid world for a few days and enjoy kayaking on the lake and reading. The cabin was very...
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    About this property
    Bring your loved one or best friend along on a Berkshires getaway in this rustic 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 serenity and unbeatable views of the Berkshire Mountains. Launch the 2...
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    Monterey, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    6.8 kilometres from Housatonic River Walk
    Studio, 2 Bathrooms, Sleeps 7 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Amenities & Details
    • Patio
    • Washer
    • Balcony
    • Air Conditioning
    • Housekeeping Included
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    other traveller has booked this property
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    Amenities & Details
    • Washer
    • Central Heating
    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 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 rustic 4-bed, 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,...
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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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    Amenities & Details
    • Waterfront
    • Terrace
    • Patio
    • Balcony
    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    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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    Monterey, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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