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Holiday Rentals near Monument Mountain

Route 7, Great Barrington, Massachusetts 01230
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    Travellers to Great Barrington are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    All 69 Rentals in Great Barrington
    Berkshires: Romantic Cottage with spectacular view1 / 18
    (24)Excellent
    4.4 kilometres from Monument Mountain
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Lakefront Berkshires Ski/Summer House, Great Views1 / 17
    (4)Very good
    6.0 kilometres from Monument Mountain
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Gem of the Berkshires, walk to downtown & lake.1 / 30
    (4)Excellent
    1.6 kilometres from Monument Mountain
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Eco-friendly cozy home in Gt. Barrington1 / 14
    (1)Very good
    2.9 kilometres from Monument Mountain
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Private Garden
    • Porch
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    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
    2.2 kilometres from Monument Mountain
    5 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 7
    Minutes from downtown Great Barrington, Convenient location1 / 14
    (33)Excellent
    5.5 kilometres from Monument Mountain
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    HOT TUB, FIREPLACE, BEAUTIFUL, COMFORTABLE, WALK TO RESTAURANTS, WEEKEND RATES!1 / 24
    (12)Excellent
    2.2 kilometres from Monument Mountain
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    3.3 kilometres from Monument Mountain
    7 Bedrooms, 7 Bathrooms, Sleeps 15 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 15
    4.6 kilometres from Monument Mountain
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
    1.2 kilometres from Monument Mountain
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Pretty Farmhouse w/ AGA Cooker - 2 Master Suites - 3 Miles to Great Barrington1 / 17
    (13)Excellent
    6.0 kilometres from Monument Mountain
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    2.0 kilometres from Monument Mountain
    3 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 11
    Renovated house on the Hill.  Walk everywhere!1 / 20
    (1)Very good
    2.0 kilometres from Monument Mountain
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    3.4 kilometres from Monument Mountain
    4 Bedrooms, 5 Bathrooms, Sleeps 7 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 7
    Classic Berkshires cottage in sun-drenched meadow1 / 25
    (1)Excellent
    6.2 kilometres from Monument Mountain
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Simply Elegant Log Home Only 3 Minutes From Butternut! Recently renovated!1 / 14
    (9)Excellent
    5.0 kilometres from Monument Mountain
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    COZY LOG HOME* fireplace, skiing,fall foliage Hiking, Berkshires*1 / 24
    (59)Very good
    3.1 kilometres from Monument Mountain
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
    Lakefront Berkshires Retreat w/ Deck, Dock & Boat!1 / 26
    (24)Average
    6.3 kilometres from Monument Mountain
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    New to Market Renovated Home, 5 min walk to town1 / 31
    (6)Excellent
    0.8 kilometres from Monument Mountain
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2.6 kilometres from Monument Mountain
    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 6
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    6.4 kilometres from Monument Mountain
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    5.0 kilometres from Monument Mountain
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    Idyllic Berkshire Get Away: Balance of relaxation and convenience1 / 18
    (17)Very good
    1.6 kilometres from Monument Mountain
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3.6 kilometres from Monument Mountain
    3 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 11
    2.7 kilometres from Monument Mountain
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    1.7 kilometres from Monument Mountain
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3.3 kilometres from Monument Mountain
    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    1.7 kilometres from Monument Mountain
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
    Charming Housatonic Village Cape1 / 29
    (21)Excellent
    6.0 kilometres from Monument Mountain
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    3.3 kilometres from Monument Mountain
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Great Barrington apartment, Short walk to downtown1 / 26
    (50)Excellent
    1.4 kilometres from Monument Mountain
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Great Barrington, Berkshires
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    4.3 kilometres from Monument Mountain
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Serene Great Barrington Cottage with Fire Pit!1 / 26
    (10)Excellent
    6.8 kilometres from Monument Mountain
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE1 / 30
    (16)Excellent
    4.4 kilometres from Monument Mountain
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    A great escape; secluded but close to all - contemporary home, mountain views1 / 35
    (2)Excellent
    4.5 kilometres from Monument Mountain
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    Upscale Country Cottage1 / 21
    (5)Excellent
    6.1 kilometres from Monument Mountain
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    1.2 kilometres from Monument Mountain
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Romantic Berkshires Cottage - Stunning Views, Pool1 / 20
    (11)Excellent
    4.3 kilometres from Monument Mountain
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Lake Community - Near Town, Attractions1 / 17
    (27)Excellent
    6.9 kilometres from Monument Mountain
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Spacious Home on the Hill w/ Pool and Hot Tub1 / 49
    (11)Excellent
    2.3 kilometres from Monument Mountain
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    5.2 kilometres from Monument Mountain
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    CHIC UPDATED DOWNTOWN Great Barrington, Sleeps 141 / 19
    (21)Excellent
    1.6 kilometres from Monument Mountain
    3 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 14
    4.7 kilometres from Monument Mountain
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    6.3 kilometres from Monument Mountain
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    6.6 kilometres from Monument Mountain
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Location Information
    Great Barrington, Berkshires
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    3.8 kilometres from Monument Mountain
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    2.3 kilometres from Monument Mountain
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
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    Location Information
    Great Barrington, Berkshires
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
    4.0 kilometres from Monument Mountain
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    4.5 kilometres from Monument Mountain
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Great Barrington, Berkshires
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    1.2 kilometres from Monument Mountain
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    stayz logo
    Check-in Check-out
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    Amenities & Details
    • Washer
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Great Barrington, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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