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Homes and Houses in Stockbridge, MA

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    Travelers to Stockbridge are booking April dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 26
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 32
    5 of 5 bubbles (4) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    5 of 5 bubbles (5) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This 1600 sq. ft. cottage boasts everything you would need for your visit to the Berkshires whether it be for a full summer / winter season to explore this beautiful area or a quick getaway to Tanglewood, The recently added master suite features a queen size bed, en-suite bathroom and a bonus... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 bubbles Reviewed 1 week ago
    Me & my son Josh had a lovely stay at the cottage. Ruth was very pleasant, the place was clean and the location was perfect. We were provided with wood for fire, the kitchen has...
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    1 / 11
    3.5 of 5 bubbles (4) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Mountain Views
    • Waterfront
    • DVD Player
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    About this property
    3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard. View all property information
    Location Information
    Stockbridge, Berkshires 01262
    4 of 5 bubbles Reviewed July 21, 2016
    The Stockbridge House was exactly what we expected from the description and pictures. The home is rustic and cozy, like a cabin in the woods. Having water access to the bowl was...
    4 of 5 bubbles Reviewed July 14, 2015
    Those who used the cottage this week ranged from me alone to one night with eight people for one night. Sleeping was not a problem. The house is ideally located between Lenox...
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    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Mountain Views
    • Patio
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    Explore the culture and natural beauty of the Berkshires while vacationing in a completely restored colonial home with modern amenities. You will be central to all the wonderful cultural attractions and outdoor activities in the area. Walk to the quaint town of Stockbridge and the Norman Rockwell... View all property information
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    Stockbridge, Berkshires 01262
    1 / 30
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house, which sleeps 6. Nestled within the serene forests of the Berkshires, ‘The Redway House’ is the quintessential setting for your next Massachusetts retreat. Welcome to ‘The Redway House’! You’ll... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 bubbles Reviewed October 23, 2016
    Awesome setting and a great outside porch complete with herb gardens(2). The forest around the property just invites a hike. Every possible thing was thought of by these...
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    1 / 21
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
    • Private Yard
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    • x
    About this property
    Our cottage is situated in a private lake community. Short walk to lake and private beach. Minutes from Tanglewood, Kripalu, Stockbridge town center and Lenox town center. Convenient to many cultural institutions, hiking, skiing. Our cottage has plenty of outdoor space for relaxing and dining.... View all property information
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    Stockbridge, Berkshires 01262
    1 / 4
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    This farmhouse has 3 bedrooms available so guests may bring their family, several friends, or overlap with new ones. The Iris Room is bright and airy with 4 windows; the Nasturtium Room has a Full bed with a half bath and the Horse room has a full and single bed across from the community... View all property information
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    Stockbridge, Berkshires 01262
    1 / 23
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Mountain Views
    • Waterfront
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    PRIVACY-QUIET- HIKE-SKI-RELAX FYI in the winter, a huge hill behind the house on our property is fantastic for sledding . Animals you might see- Turkeys, Ducks, Bobcat, Bear, Deer, Otter, Muskrat, Heron depending on the season. A 1/4 mile driveway thru the woods takes you to 38 acres, and this... View all property information
    Location Information
    Stockbridge, Berkshires 01260
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    1 / 4
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Private Yard
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    About this property
    This 1762 farmhouse features wide board floors, kitchen, dining and living room areas along with a spacious front porch. Agritour gardens, horseback riding, and close proximity to Tanglewood and the Norman Rockwell Museum make for an adventure filled visit. Larry prepares a great fresh egg... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 4
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    The 1762 farmhouse has 3 bedrooms available to bring your family and friends enjoy the close proximity to Tanglewood, Norman Rockwell Museum, and several lakes, many hiking areas, great restaurants. Larry makes a fresh egg breakfast which is included in your stay. You can join us for horseback... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    About this property
    Completely renovated vacation home with state of the art kitchen and marble baths, centrally located in the Berkshires 3 miles from Tanglewood, on 10 acres on a quiet country road. New in-ground pool surrounded by patio and expansive deck and pool house nestled in the woods. Central air... View all property information
    Location Information
    Stockbridge, Berkshires 01262
    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Amenities & Details
    • Internet Access
    • Patio
    • Waterfront
    • Central Heating
    • Satellite TV
    • Porch
    • Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Stockbridge, Berkshires 01236
    1 / 9
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Beautifully appointed farm house situated on 200 acres of this pristine estate located in the heart of the Berkshires. This home offers three bedrooms, three bathrooms, fully equipped kitchen, laundry room, deck and porch. Perfectly located to all The Berkshires attractions, This home is within 4... View all property information
    Location Information
    Stockbridge, Berkshires