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Holiday Rentals in Tyringham

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    All 28 Rentals in Tyringham
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    Romantic Berkshire Cottage on Storybook Estate1 / 10
    (1)Excellent
    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Tyringham
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Charming and Spacious Colonial Farmhouse on 4 Acre Estate1 / 15
    (1)Average
    Tyringham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Santarella Estate and Gardens in Tyringham, MA is a magical destination in the heart of one of the Berkshires' most beautiful valleys, located 3 miles from Interstate 90 and 15 minutes from most of the principal attractions (Tanglewood, Jacob's Pillow, Norman Rockwell museum, etc.) Pictures are...
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    Tyringham, Berkshires 01264
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A bright, lovely and comfortable room with queen bed in a charming country farmhouse with adjoining private bath. Located in Tyringham, a bucolic, rural village on a scenic country road the beautiful and magical 'Hop Brook' valley. The house is surrounded by farmland surrounding it on all sides. A...
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    Tyringham, Berkshires 01264
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The following rentals are within 10 kilometers of Tyringham.
    The Playhouse: 7,000 Sq Feet of Berkshires Luxury1 / 21
    (4)Excellent
    Lee
    6 Bedrooms, 5 Bathrooms, Sleeps 26 Quick View
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    • Private Garden
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 April 2017
    First impressions were that it was amazing as the description - real wow factor. Equipped with everything you could want. The socialising space was amazing, with room for all 19...
    Reviewed 21 December 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...
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    About this property
    220 acres with yoga studio 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 in-house yoga...
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    Lee, Berkshires 01238
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 26
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    The Gatehouse on Golden Hill1 / 13
    (1)Excellent
    Lee
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Secure Parking
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 October 2017
    Stayed for 4 nights. Very spacious and well maintained. Greeted by Peter with prosecco, cheese, crackers,tomatoes, mint from the garden, and donuts. He gave us an orientation...
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    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,...
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    Lee, Berkshires 01238
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Jacob's Tanglewood Ranch (great for groups 10+)1 / 46
    (2)Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • Wi-Fi
    • Porch
    • Air Conditioning
    • Balcony
    • Washer
    • Mountain Views
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2017
    Excellent location to enjoy the best of the Berkshires, and a comfortable, spacious house full of historic character. 3 wood burning fireplaces and a screened porch make this...
    Reviewed 30 May 2016
    My family loved this house - parents and kids, all found it comfortable, spacious, and welcoming. Host is accommodative on last-minute changes or special requests. Easy...
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    About this property
    In the heart of the Berkshires: near Tanglewood, Jacob's Pillow, Jiminy Peak, Ski Butternut, Lenox MA, Stockbridge MA. Completely restored historic house with fully equipped kitchen, 5 bedrooms (each with a private bathroom), 3 spacious common rooms. A comfortable place for a family reunion,...
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    Lee, Berkshires 01238
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 20
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    little blue cottage lots of cute! 1 mile to stockbridge center . pet friendly!1 / 12
    (1)Very good
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Internet Access
    • Porch
    • Parking
    • Mountain Views
    • Cable/satellite TV
    • Grill
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 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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    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...
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    Lee, Berkshires 01238
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Lake House1 / 19
    (4)Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Wi-Fi
    • DVD Player
    • Sauna
    • Air Conditioning
    • Grill
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 September 2016
    My family and I traveled to the Berkshires from Boston and stayed in this gorgeous lake house. We had booked vacation rentals in the past and had a whole range of experiences...
    Reviewed 1 September 2016
    We stayed at the Lake House on beautiful Laurel Lake with my family of 5 (two daughters, son, and my wife). We had an awesome time. The owners Marjorie and Frank were wonderful...
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    About this property
    Custom designed Furnished Lake House in The Berkshires in Massachusetts on the Lee/Lenox line. Gorgeous western sunsets ! The home has 4/5 bedrooms and one is equipped as a nanny suite or teen haven. It is close to skiing, golf, outdoor sports, shopping, and all cultural venues. It is located...
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    Lee, Berkshires 01238
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 9
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    Spacious Lakeside Berkshire Home1 / 23
    (1)Excellent
    Monterey
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    • DVD Player
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 September 2017
    What impressed us all is the spacious, clean, well organized place. The owner had well documented suggestions of all nearby sightseeing places as well as restaurants. The...
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    About this property
    The lakeside house is built on a 1.1 acre lot with view of Lake Garfield. It is only three minute walk to the public beach with life guards on site. In the summer, Jacob’s Pillow Dance Center and Tanglewood Music Center are about 25 to 30 minutes away. In the winter, Ski Butternut resort is about...
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    Monterey, Berkshires 01245
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Lee
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    --Brand new 3400 sq ft Lee home in a private lake community, Berkshires --Situated on 4 wooded acres on a quiet country road --Pristine home features two master bedroom suites plus 3 additional bedrooms, 5 bathrooms --Spacious living room with vaulted ceiling & skylights --Fully equipped kitchen,...
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    Lee, Berkshires 01238
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Perfect Getaway for Body, Mind and Soul1 / 24
    (2)Excellent
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Parking
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Internet Access
    • Porch
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Lee, Berkshires 01238
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Lee
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Cable/satellite TV
    • Shared Indoor Pool
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have a corner unit first floor 2-bed resort presidential suite in beautiful Berkshires! Just 2 hours drive down the Mass Pike from Boston. It's July 4th week and James Taylor will be playing at Tanglewood. This is one of the most sought after concerts every year and you wouldn't want to miss it!...
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    Lee, Berkshires 01238
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Berkshires Spacious Comfortable Charming Farmhouse1 / 12
    (2)Very good
    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Internet Access
    • Parking
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 June 2013
    This property was a great home base for our brief visit to the Berkshires. Plenty of space and well equipped. We especially enjoyed the beautiful property, whether sitting on...
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    About this property
    Experience a little of old New England. Our vacation rental is a charming historic family farmhouse apartment with lots of room and comfort,2100Sq.ft., situated on 22 acres. Built in 1782, our farm was famous for breeding Plymouth Barred Rock chickens. In the 1800's, one of these barred rock...
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    Lee, Berkshires 01238
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    chestnut lodge Queens Room1 / 2
    (1)Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Reviewed 16 August 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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    About this property
    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...
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    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Berkshires House, 40 wooded acres, Lake Frontage1 / 16
    (19)Very good
    Monterey
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Grill
    • Washer
    • Waterfront
    • Mountain Views
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 September 2017
    We rented Karl's house for a 10-day time frame, to enjoy some family vacation time with our children and grandchildren. I have really struggled with what to say about this...
    Reviewed 18 November 2015
    I took my wife and three young children up to this house for columbus day week. We had a blast. The house has a real cabin in the woods feel and is just a short walk to the...
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    About this property
    Charming house with the feeling of a cottage, set on a knoll with adjacent cathedral-like pine forest. **The house has a Jacuzzi and ROKU access to online (cable) TV. ** Stone fireplace, woodstove, beautiful kitchen with modern appliances (gas stove, microwave, refrigerator with water/ice...
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    Monterey, Berkshires 01245 0933
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Patio
    • Shared Garden
    • Parking
    • Mountain Views
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is the second floor of the barn. this is ver rustic, literally a 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...
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    Lee, Berkshires 01238
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Monterey
    5 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get away from it all at our beautiful Berkshire lakefront wooded retreat. Swim, canoe, kayak, sunbathe, play tennis during the day, then enjoy the evening a short drive away at Tanglewood, Jacobs Pillow, or perhaps go to the movies in Great Barrington. Have dinner at the Red Lion Inn, or one of the...
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    Monterey, Berkshires 01245
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    sleeps 4 can combine with writer's room for large suite, private entrance. fireplace or windowed woodstove, ceiling fans cathedral ceiling, terrace with seating, pasture and forest views. windows line both sides of room and feels like a treehouse. beautiful wood floors and soft carpets make you...
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    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Writer's Room at Chestnut Lodge1 / 8
    (1)Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Hot Tub
    • Outdoor Dining Area
    • Mountain Views
    • Internet Access
    • Air Conditioning
    • Balcony
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 June 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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    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....
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    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Lee
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • DVD Player
    • Terrace
    • Balcony
    • Washer
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the tranquil hills of the beautiful Berkshires. This truly is a wooded wonderland filled with restful beauty and abundant wildlife. Wonderful retreat in the Berkshires. Private and secluded. Minutes from Tanglewood, The Red Lion Inn and The Norman Rockwell museum. Skiing. Private lake...
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    Lee, Berkshires 01238
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Lee
    1 Bedroom, 2 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
    • Washer
    • Internet Access
    • Parking
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note that homeowner lives in a separate building on the property and may be present during your stay* Gather your loved ones for a revitalizing Lee retreat when you book this lovely 1-bedroom, 2-bathroom vacation rental house that comfortably sleeps 9! With a spacious loft, private deck,...
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    Lee, Berkshires 01238
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 9
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    Monterey
    Studio, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You'll love our hand-hewn post & beam beauty on 13 acres in the Berkshire Mountains of Western Mass located near the Monterey/Great Barrington line, close to everything. Great for summer and winter ski season. Rich in both outdoor and cultural attractions, shopping and antiquing. Located adjacent...
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    Monterey, Berkshires 01245
    Holiday Rental House - 2 Bathrooms, Sleeps 7
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    Berkshire House Share-The Blue Room1 / 10
    (1)Excellent
    Lee
    3 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Share a beautifully renovated home in the Berkshire Mountains of Western MA. I would prefer a long-term housemate, but will be glad to do weekend or short term stays. Long-term pricing can be negotiable. Cable TV (in your room), internet, washer and dryer, big eat-in kitchen, well-lit living room....
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    Lee, Berkshires 01238
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 2
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    Lee
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Private Garden
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a completely renovated house that is situated on a private street, 5 min walk to the most beautiful beach on Laurel Lake, as well as 5 min drive to either Lee center or Lenox center. The main floor has an open layout that is full of light. The gourmet kitchen is fitted with top appliances...
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    Lee, Berkshires 01238
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Lee
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1400 square foot, three bedroom home has all amenities including washer and dryer in basement. Electric heat and oven. Front porch and back deck. First floor is open floor plan with kitchen, dining area and living room flowing from one to the other. Skylights in the living/dining area and...
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    Lee, Berkshires 01240
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Patio
    • Cable/satellite TV
    • Central Heating
    • Porch
    • Wi-Fi
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Share a beautifully renovated Victorian home, in downtown Lee, Ma, right in the heart of the Berkshires. Walking distance to town, and on the bus line. Wifi, cable TV, off street parking. Shared kitchen and bath. I have two cats and one other housemate. I am a gospel and blues musician. This is a...
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    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 1
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