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Vacation Rentals near Housatonic River Walk

195 Main St, Great Barrington, Massachusetts 01230-1602
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    Travelers to Great Barrington are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    All 87 Rentals in Great Barrington
    Berkshires: Romantic Cottage with spectacular view1 / 18
    (24)Excellent
    2.2 miles from Housatonic River Walk
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Lakefront Berkshires Ski/Summer House, Great Views1 / 17
    (4)Very good
    3.8 miles from Housatonic River Walk
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Gem of the Berkshires, walk to downtown & lake.1 / 30
    (4)Excellent
    0.3 miles 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
    1.6 miles 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Beautiful Period Home in the Berkshires1 / 21
    (31)Excellent
    4.3 miles from Housatonic River Walk
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Great Barrington, Berkshires
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    0.7 miles from Housatonic River Walk
    5 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Great Barrington, Berkshires
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 7
    HOT TUB, FIREPLACE, BEAUTIFUL, COMFORTABLE, WALK TO RESTAURANTS, WEEKEND RATES!1 / 24
    (12)Excellent
    0.5 miles from Housatonic River Walk
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Great Barrington, Berkshires
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    2.7 miles from Housatonic River Walk
    7 Bedrooms, 7 Bathrooms, Sleeps 15 Quick View
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    Great Barrington, Berkshires
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 15
    Amazing Ski Lodge - Incredible 7,500 Sq. Ft. Log Cabin1 / 21
    (19)Excellent
    3.6 miles from Housatonic River Walk
    5 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    Great Barrington, Berkshires
    Rental Home - 5 Bedrooms, 7 Bathrooms, Sleeps 20
    2.7 miles from Housatonic River Walk
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Great Barrington, Berkshires
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    Impeccable House Minutes from Downtown Great Barrington1 / 19
    (3)Very good
    0.6 miles from Housatonic River Walk
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    1.5 miles from Housatonic River Walk
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Great Barrington, Berkshires
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    5.3 miles from Housatonic River Walk
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Great Barrington, Berkshires
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    3.8 miles from Housatonic River Walk
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Great Barrington, Berkshires
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.4 miles from Housatonic River Walk
    3 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    Great Barrington, Berkshires
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 11
    Renovated house on the Hill.  Walk everywhere!1 / 19
    (1)Very good
    0.4 miles from Housatonic River Walk
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Great Barrington, Berkshires
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    1.6 miles from Housatonic River Walk
    4 Bedrooms, 5 Bathrooms, Sleeps 7 Quick View
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    Great Barrington, Berkshires
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 7
    Simply Elegant Log Home Only 3 Minutes From Butternut! Recently renovated!1 / 13
    (9)Excellent
    3.5 miles from Housatonic River Walk
    5 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Great Barrington, Berkshires
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 5
    Classic Berkshires cottage in sun-drenched meadow1 / 24
    (3)Excellent
    3.0 miles from Housatonic River Walk
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    COZY LOG HOME*The Berkshires*  Hiking*  Skiing**Gt. Barrington *fireplace1 / 25
    (59)Very good
    2.5 miles from Housatonic River Walk
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Skiing: Property Is In A Ski Resort
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    Great Barrington, Berkshires
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    1.6 miles from Housatonic River Walk
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Lakefront Berkshires Retreat w/ Deck, Dock & Boat!1 / 25
    (25)Average
    4.0 miles from Housatonic River Walk
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Great Barrington, Berkshires
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    New to Market Renovated Home, 5 min walk to town1 / 29
    (6)Excellent
    0.3 miles from Housatonic River Walk
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Great Barrington, Berkshires
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Newly Remodeled Private Estate! Pool, Tennis Court, 5 Mins to Town & Ski Resorts1 / 29
    (18)Excellent
    1.7 miles from Housatonic River Walk
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Great Barrington, Berkshires
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    0.6 miles from Housatonic River Walk
    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Great Barrington, Berkshires
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 6
    4.1 miles from Housatonic River Walk
    4 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Great Barrington, Berkshires
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 4
    3.8 miles from Housatonic River Walk
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Great Barrington, Berkshires
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    4.1 miles from Housatonic River Walk
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Great Barrington, Berkshires
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    The Freeman - Newly Renovated 14K SF Estate on 40 Acres1 / 29
    (15)Excellent
    4.9 miles from Housatonic River Walk
    5 Bedrooms, 5 Bathrooms, Sleeps 25 Quick View
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    Great Barrington, Berkshires
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 25
    3.5 miles from Housatonic River Walk
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Great Barrington, Berkshires
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    Idyllic Berkshire Get Away: Balance of relaxation and convenience1 / 17
    (21)Very good
    1.3 miles from Housatonic River Walk
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Great Barrington, Berkshires
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2.6 miles from Housatonic River Walk
    3 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Great Barrington, Berkshires
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 11
    0.8 miles from Housatonic River Walk
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    0.2 miles from Housatonic River Walk
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Great Barrington, Berkshires
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    1.2 miles from Housatonic River Walk
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    About this property
    Just far enough outside of town to feel like you're getting away with all the conveniences of being a mile from great bars and restaurants, the Mahaiwe theater, 3 grocery stores, a cheese shop, a movie theater, multiple coffee shops, pastries, Saturday Farmer's Market, and fabulous boutiques. Do...
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    Great Barrington, Berkshires
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.2 miles from Housatonic River Walk
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    1.2 miles from Housatonic River Walk
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Great Barrington, Berkshires
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    2.3 miles from Housatonic River Walk
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Great Barrington, Berkshires
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Great Barrington apartment, Short walk to downtown1 / 25
    (56)Excellent
    0.0 miles 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
    Serene Great Barrington Cottage with Fire Pit!1 / 25
    (11)Excellent
    3.4 miles from Housatonic River Walk
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Great Barrington, Berkshires
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    A great escape; secluded but close to all - contemporary home, mountain views1 / 29
    (2)Excellent
    3.1 miles from Housatonic River Walk
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Great Barrington, Berkshires
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    Upscale Country Cottage1 / 21
    (5)Excellent
    3.2 miles from Housatonic River Walk
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Great Barrington, Berkshires
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Stay in Town, Enjoy Late Check Out1 / 19
    (3)Excellent
    0.2 miles from Housatonic River Walk
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Great Barrington, Berkshires
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Romantic Berkshires Cottage - Stunning Views, Pool1 / 19
    (27)Excellent
    2.1 miles from Housatonic River Walk
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Great Barrington, Berkshires
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    Spacious Home on the Hill w/ Pool and Hot Tub1 / 29
    (13)Excellent
    0.6 miles from Housatonic River Walk
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Internet Access
    • Cable/satellite TV
    • Washer
    • Private Outdoor Pool (Unheated)
    • Parking
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Great Barrington, Berkshires
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    2.9 miles from Housatonic River Walk
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Hot Tub
    • Air Conditioning
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Great Barrington, Berkshires
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 12
    3.5 miles from Housatonic River Walk
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Washer
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    Pet friendly
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    Location Information
    Great Barrington, Berkshires
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    CHIC UPDATED DOWNTOWN Great Barrington, Sleeps 141 / 18
    (22)Excellent
    0.2 miles from Housatonic River Walk
    3 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Balcony
    • Grill
    • Terrace
    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Great Barrington, Berkshires
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 14
    Just you, the lake and the brilliant fall foliage1 / 23
    (16)Excellent
    3.6 miles from Housatonic River Walk
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Skiing: Property Is In A Ski Resort
    • Terrace
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Great Barrington, Berkshires
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    5.3 miles from Housatonic River Walk
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Patio
    • Internet Access
    • Parking
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Great Barrington, Berkshires
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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