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Holiday Rentals in Stockbridge

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    Travellers to Stockbridge are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    All 44 Rentals in Stockbridge
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    Spring Break Special!  Stay two nights get one free for March and April!1 / 22
    (21)Excellent
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Centrally Located Contemporary Gem In Stockbridge1 / 40
    (25)Excellent
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    STOCKBRIDGE  One Of The Finest Homes and Best Locations... Walk To Beach1 / 49
    (35)Excellent
    Stockbridge
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Stockbridge! 1/2 mile from Red Lion inn.  Great Barrington, Lenox, Lee close by.1 / 31
    (38)Excellent
    Stockbridge
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    A Grand Estate in Historic Stockbridge1 / 26
    (34)Excellent
    Stockbridge
    6 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 12
    Stockbridge Cape Near Tanglewood & Kripalu - Heart Of The Berkshires!1 / 24
    (46)Excellent
    Stockbridge
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country1 / 28
    (45)Excellent
    Stockbridge
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    General Williams Estate House Lenox/Stockbridge1 / 29
    (44)Excellent
    Stockbridge
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Stockbridge, Berkshires 01238
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
    Renovated Colonial on the River! Fantastic Views1 / 21
    (29)Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Stockbridge, Berkshires 01236
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Family-Friendly Cottage Off Lake in Stockbridge1 / 31
    (12)Excellent
    Stockbridge
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Stockbridge, Berkshires 01240
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Stockbridge
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    Charming Stockbridge Historic Home a Stones Throw Away from the Red Lion INN1 / 33
    (10)Very good
    Stockbridge
    11 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    Stockbridge, Berkshires 01263
    Holiday Rental House - 11 Bedrooms, 8 Bathrooms, Sleeps 24
    Sophisticated &  Comfortable Stockbridge Retreat  A+ Location  Modern Amenities1 / 43
    (5)Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Greek Revival Style Farmhouse Circa 18201 / 14
    (27)Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Exempt From Public Haunt - 1 mile from Red Lion Inn1 / 36
    (2)Excellent
    Stockbridge
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    Stockbridge
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    Historic Colonial, 2 Minute Walk to Stockbridge Village & Hikes1 / 18
    (5)Excellent
    Stockbridge
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Beautifully Restored 1820s Industrial Loft Living On A Creek1 / 31
    (9)Excellent
    Stockbridge
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Private lakeside 1920's cottage near Tanglewood1 / 22
    (5)Excellent
    Stockbridge
    4 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 10
    Stockbridge
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Beautiful Berkshire Cabin Close to All Attractions and Beach1 / 8
    (18)Very good
    Stockbridge
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
    PERFECT SuMMER HOUSE WITH HEATED POOL1 / 11
    (7)Excellent
    Stockbridge
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Holiday in Norman Rockwell's Stockbridge1 / 12
    (3)Very good
    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Stockbridge
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Shared Indoor Pool
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    • Sauna
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    Stockbridge, Berkshires 01262
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Stockbridge
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Two Blocks from the Red Lion Inn & next to Berkshire Theater1 / 12
    (2)Very good
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Stockbridge renovated classic1 / 25
    (1)Excellent
    Stockbridge
    4 Bedrooms, 8 Bathrooms, Sleeps 8 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 8 Bathrooms, Sleeps 8
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2 miles to Kripalu, Tanglewood, small house (sleeps up to 4)1 / 10
    (4)Excellent
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Stockbridge
    7 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 12
    Stockbridge
    7 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Stockbridge, Berkshires 01263
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 10
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 11
    Stockbridge
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Convenient to Beach, Tanglewood and All Berkshire Amenities1 / 14
    (3)Very good
    Stockbridge
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Stockbridge
    4 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 7
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 5
    Stockbridge
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
    Peaceful Woodland Home in the Heart of the Berkshires1 / 32
    (23)Very good
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Stockbridge, Berkshires 01229
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
    Stockbridge
    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 4
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Stockbridge
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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