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Homes and Houses in Stockbridge, MA and nearby

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    1 / 16
    5 of 5 bubbles (5) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    1 / 32
    5 of 5 bubbles (5) Excellent
    Stockbridge
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    1 / 25
    5 of 5 bubbles (1) Excellent
    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 17
    5 of 5 bubbles (1) Excellent
    Stockbridge
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Mountain Views
    • Patio
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    • 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
    Location Information
    Stockbridge, Berkshires 01262
    5 of 5 bubbles Reviewed January 4, 2017
    Our family of four absolutely loved our stay in Melanie and Henry's home. After communicating with Melanie before our arrival, we felt welcome before we stepped into the house...
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    1 / 26
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Newly renovated contemporary house on 2 acres in Stockbridge. Great space surrounding house for outdoor sports and sitting around the fire at night. 3 bedrooms, 3 bathrooms, indoor fireplace, wood floors, many windows and closets. Large kitchen. WiFi. Master bedroom has king bed and master... View all property information
    Location Information
    Stockbridge, Berkshires 01238
    1 / 30
    5 of 5 bubbles (1) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    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
    Stockbridge
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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 / 11
    3.5 of 5 bubbles (4) Average
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Mountain Views
    • Waterfront
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    • Pet-friendly
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    • ?
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    • x
    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 / 20
    5 of 5 bubbles (1) Excellent
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Internet Access
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    • Waterfront
    • Central Heating
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    • x
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    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
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    Stockbridge, Berkshires 01236
    1 / 22
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    1 / 4
    Stockbridge
    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 / 4
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    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
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    Stockbridge, Berkshires 01262
    1 / 4
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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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
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    Stockbridge, Berkshires 01262
    1 / 24
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Balcony
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    Stockbridge, Berkshires 01262
    1 / 24
    Stockbridge
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Stockbridge, Berkshires 01229
    1 / 20
    Stockbridge
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Stockbridge, Berkshires 01263
    1 / 23
    Stockbridge
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Sauna
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    • x
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    Stockbridge, Berkshires 01262
    1 / 19
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Stockbridge, Berkshires 01262
    1 / 22
    Stockbridge
    6 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    Stockbridge, Berkshires 01238
    1 / 14
    Stockbridge
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Stockbridge, Berkshires 01262
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    1 / 24
    Stockbridge
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Stockbridge, Berkshires 01262
    1 / 23
    Stockbridge
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Patio
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    Stockbridge, Berkshires 01240
    1 / 24
    Stockbridge
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Stockbridge, Berkshires 01262
    1 / 24
    Stockbridge
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Stockbridge, Berkshires 01266
    1 / 14
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Stockbridge, Berkshires 01262
    1 / 21
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    Stockbridge, Berkshires 01236
    1 / 24
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    Stockbridge, Berkshires 01262
    1 / 24
    Stockbridge
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Stockbridge, Berkshires 01262
    1 / 12
    Stockbridge
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Stockbridge, Berkshires 01262
    1 / 24
    Stockbridge
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Balcony
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    Stockbridge, Berkshires 01262
    1 / 24
    Stockbridge
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Stockbridge, Berkshires 01262
    1 / 17
    Stockbridge
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Stockbridge, Berkshires 01262
    1 / 23
    Stockbridge
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    Stockbridge, Berkshires 01262
    1 / 8
    Stockbridge
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    Stockbridge, Berkshires 01262
    1 / 16
    Stockbridge
    5 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    Location Information
    Stockbridge, Berkshires 01262

    The following rentals are within 5 miles of Stockbridge, Massachusetts.

    1 / 21
    5 of 5 bubbles (3) Excellent
    Lee
    6 Bedrooms, 5 Bathrooms, Sleeps 26 | Quick View
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    • Private Yard
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    • x
    About this property
    220 acres with tennis, yoga studio, gym and lakefront. Built by Westinghouse and then part of the Vanderbilt Estate, The Playhouse is a newly renovated iconic Berkshire's property that once served as a theater space for America's greatest innovators, and is now hung with fine art, and includes an... View all property information
    Location Information
    Lee, Berkshires 01238
    5 of 5 bubbles Reviewed December 21, 2016
    The Playhouse provides all that is necessary to have a fabulous time with family or a large group. I have looked for a place to hold our annual family Christmas gathering for...
    5 of 5 bubbles Reviewed August 11, 2016
    The Playhouse is a magical place to connect with friends and family. There are a half dozen living spaces that offer anything from quiet reading areas with a view, to 40 person...
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    1 / 12
    4 of 5 bubbles (1) Very good
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Porch
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    • Mountain Views
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    • Pet-friendly
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    • x
    About this property
    cute cozy cottage, screened porch with views, close to everything, sleeps 2 nice yard with big old trees and soft grass. gas bbq, just one mile to stockbridge center , Berkshire theatre festival. 5 miles to tanglewood, lenox , kripalu. 10 minutes to great barrington. bath has shower. full... View all property information
    Location Information
    Lee, Berkshires 01238
    4 of 5 bubbles Reviewed August 12, 2016
    We stayed at Jo-Anne's cottage for a week in mid-July. Wasn't sure what to expect as the place had no reviews. Our hostess made us feel at home right away and made a major...
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    1 / 23
    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Completely renovated 2 bedroom downtown apartment with open floor plan in Lenox MA. Enjoy walks around the downtown area and visit the many attractions in Berkshire County. Endless restaurants to choose from, golf courses within 7 miles, Kennedy Park and Tanglewood close by. Minutes down the road... View all property information
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    Lenox, Berkshires 01240
    1 / 20
    5 of 5 bubbles (26) Excellent
    West Stockbridge
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Central Heating
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16" floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer,... View all property information
    Location Information
    West Stockbridge, Berkshires 01266
    4 of 5 bubbles Reviewed January 2, 2017
    This Berkshire Farmhouse worked out great for our 3 family reunion. The house was clean, stocked with plenty of blankets and towels, as well as many other amenities. The owner...
    5 of 5 bubbles Reviewed May 9, 2016
    Our group of eight adults had a very wonderful experience at Elaine's Berkshire farmhouse. We found it in excellent condition. Full kitchen had everything we needed to create...
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    1 / 24
    5 of 5 bubbles (2) Excellent
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Mountain Views
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    • x
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    • x
    About this property
    ** Rental is only available for 2 week minimum during the summer (July - August) Special Summer Deal -- Rent for the Season (July and August) and get either the last week in June OR the first week in September for half price! This adorable cottage has all the ingredients for the ultimate retreat... View all property information
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    Lee, Berkshires 01238
    1 / 8
    5 of 5 bubbles (1) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    The Writer's Room is at the top of the stairs on the right. This handsome room is made completely of wood. Ceilings are higher and there's a sitting area in the big dormer. dormer faces east and get the morning sun! The floors are wide plank cherry milled from the property. the walls are pine.... View all property information
    Location Information
    Lee, Berkshires 01238
    5 of 5 bubbles Reviewed June 17, 2014
    We have taken the Writer's Room each Summer for about three years now. We find the Lodge to be authentic New England... our natural wood room to the rest of the house. It is...
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    1 / 4
    5 of 5 bubbles (1) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    first floor queensized bed, bath with shower. floors are wood ceiling has exposed beams and is furnished with oak antiques and a big wingbacked chair.built in bookshelf was from a companionway on a wooden sailing vessel owned by a sea captain that owned and ran the lodge back at the turn of the... View all property information
    Location Information
    Lee, Berkshires 01238
    5 of 5 bubbles Reviewed June 17, 2014
    And I hope to stay here again in the future. I feel very comfortable here - good privacy, the house is huge, rustic charm, generally very quiet. The property is massive - and the...
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    1 / 17
    5 of 5 bubbles (2) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 6 | Quick View
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    • Outdoor Dining Area
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    • Pet-friendly
    • Child-friendly
    • ?
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    About this property
    handsome and welcoming, this authentic Berkshire lodge will make you feel like you`re in an old fashioned Christmas card! fireplace blazing, wood floors post and beam, hand planed planks. in the kitchen the floor is marble slabs from the famous lee marble quarry. Daniel Chester French, the designer... View all property information
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    Lee, Berkshires 01238
    5 of 5 bubbles Reviewed October 11, 2015
    Rustic and vintage are apt descriptions of the house itself. It has stories to tell! And to matched its abundant, well aged charm is the friendly and generous host. Joanne made us...
    5 of 5 bubbles Reviewed June 12, 2014
    I had several summer months here, it never disappoints. Full of nature's bounty, hospitable host, friendly vacationers. Very close to all the best of the Berkshires, Tanglewood...
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    Lenox
    4 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
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    • Pet-friendly
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    220 acre Fox Hollow Estate with 1000 feet of Lake Front on Laurel Lake. 8 Person Hot tub on deck. Fabulous deck fire pit, outdoor furniture and gas grill. Fireplace to warm up by. High ceilings, open living concept. 2400 sq. feet with 4 BR's on main level each with private bath, TV and DVD. 3... View all property information
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    Lenox, Berkshires 01240
    1 / 2
    5 of 5 bubbles (1) Excellent
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    Sunny, light , bright and wide! the queens room is one of the biggest rooms and has private ensuite bathroom with tub/shower. 2 big closets, large writing desk, comfy conversation area, 2 dressers full sized bed. a section of the room has original ceilings so persons taller than 6'2" would be... View all property information
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    Lee, Berkshires 01238
    5 of 5 bubbles Reviewed August 16, 2015
    I had the pleasure of staying at the Chestnut Lodge in the Queen's room. From the moment you step into the foyer you are taken back to a simpler time in this historic lodge. The...
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    1 / 13
    Lee
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Air Conditioning
    • Secure Parking
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    • x
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    • x
    About this property
    We are located in the heart of America's cultural epicenter known as the Berkshires. Known as the "Gatehouse" to upscale Erskine Park, this truly one of a kind Craftsmen inspired home is filled with unique features and materials seldom found including eucalyptus and Brazilian Cherry flooring,... View all property information
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    Lee, Berkshires 01238
    1 / 10
    5 of 5 bubbles (1) Excellent
    West Stockbridge
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Grill
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    • Patio
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    • DVD Player
    • Mountain Views
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Rent a comfortable 1840 farmhouse with 26 acres in the Berkshire mountains. Walk to the village of West Stockbridge or a short drive to all the Berkshire attractions. Close to the ski resorts of Butternut, Bousquet, Catamount and Jiminy Peak. The house sleeps 10 to 12 people and is fully equipped.... View all property information
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    West Stockbridge, Berkshires 01266
    5 of 5 bubbles Reviewed October 18, 2016
    We had a wonderful time staying at this property. The house is full of charming details - we kept discovering art objects till the time of our departure. The kids had fun using...
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    1 / 6
    Lee
    1 Bedroom, 3 Bathrooms, Sleeps 5 | Quick View
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    • Grill
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    • Shared Yard
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    • Pet-friendly
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    • ?
    • x
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    • x
    About this property
    This is the second floor of the barn. Open cathedral ceiling. Wooden interior with open floor plan. Big queen sized bed with canopy . 2 twin beds. Great for traveling with family or friends. Kitchen area has microwave, mini fridge, induction cooktop, hot pot and coffeemaker. Bathroom has... View all property information
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    Lee, Berkshires 01238
    1 / 30
    Lenox
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • Wi-Fi
    • Private Yard
    • Patio
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    • Air Conditioning
    • Satellite TV
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    AS YOU OPEN THE GATE FROM THE DRIVE YOU WALK ONTO YR FRONT DECK LEADING TO THE ENTRY , MUD ROOM WHICH HOLDS YR SUMMER NEEDS, SKIS AND BOOTS. THIS LEADS TO THE COTTAGE APT. [attached to the owner`s quarters} LIVING RM- HAS A SOFA SLEEPER TO ACCOMMODATE 2 MORE GUESTS. KITCHENETTE W/ LG CEILING... View all property information
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    Lenox, Berkshires 01240
    1 / 10
    Lee
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Parking
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    • Mountain Views
    • Outdoor Dining Area
    • Balcony
    • Patio
    • Hot Tub
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    the garden room is a small room with a full sized bed. everything is floral, even the closet walls. it 's a sweet room with even a wood stove. it has an entrance to the courtyard just outside in the hall, the bath may be shared depending on the situation. bath has shower and lovely old sink. bath... View all property information
    Location Information
    Lee, Berkshires 01238
    Stockbridge Flight and Weather Info
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    BDL
    Bradley Intl Airport
    39.9 miles from Stockbridge
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