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Holiday Rentals nearby Tanglewood

West St off Rte 183, Lenox, Massachusetts 01240
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    24 Matching Rentals in the Lenox AreaView all 34 rentals
    Gartner House, a charming home in Lenox1 / 21
    (33)Excellent
    Lenox
    2.6 kilometres from Tanglewood
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Heart of Lenox1 / 7
    (2)Excellent
    Lenox
    2.7 kilometres from Tanglewood
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lenox
    2.4 kilometres from Tanglewood
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Lenox
    3.9 kilometres from Tanglewood
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
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    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fabulous great room with pool table, 65' HD Smart TV for you sports fans. Great indoor / outdoor sound system and don't worry about the neighbors. Summer weeks include 2 rounds of golf at nearby Cranwell Country club or Spa treatments for two at the Cranwell Spa or trade them for show tickets,...
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    Lenox, Berkshires
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
    Lenox
    2.4 kilometres from Tanglewood
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Lenox, Berkshires
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Lenox
    0.6 kilometres from Tanglewood
    5 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Hot Tub
    • Grill
    • Balcony
    • Housekeeping Included
    • Terrace
    • Patio
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    5 BR, 5 Full Bath's (Jetted tub), Newly Expanded open floor plan, 3 fireplaces, firepit, grill, large outdoor patio, screened porch, sleeps 15+. Large backyard with volleyball, football, badminton, bocce, croquet, ping pong and hammock. About 600 feet to Tanglewood Music Center. Across the street...
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    Lenox, Berkshires
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 15
    Lenox
    3.9 kilometres from Tanglewood
    4 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    Pet friendly
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    About this property
    Smart New first time rental of 4 BR, 4.5 BA, Ranch style, sleeps 10-12+. New fully equipped kitchen w/breakfast bar, outdoor barbecue, fireplace, large deck with 8 person hot tub and super seating for beautiful sunsets, . Fabulous great room with 65' HD Smart TV and 4 additional TV's for you...
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    Lenox, Berkshires
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 11
    Lenox
    4.0 kilometres from Tanglewood
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quintessential Lenox Farmhouse with 1881 charm and a shiny new finish. Lovingly renovated and restored, this house is nestled on 4.5 private acres within minutes of the town of Lenox and Tanglewood. The house boasts a chef's Kitchen with all new stainless steel appliances, large farmhouse porcelain...
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    Lenox, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Lenox
    2.5 kilometres from Tanglewood
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Washer
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy leisurely lakeside days just a walk away as you stay at this 3-bed, 1.5-bath vacation rental house that sleeps 6 in Stockbridge! With mossy grounds below and age-old oaks towering above, this cozy cottage is a dreamy retreat, perfect for those looking for a bit of the great outdoors without...
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    Lenox, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Lenox
    5.2 kilometres from Tanglewood
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Mountain Views
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated in the heart of the Berkshires, this 3-bed, 2-bath vacation rental offers a modern living space, a large yard and an ideal location near many attractions. Adventure seekers will enjoy easy access to the Appalachian Trail and Catamount Ski Resort, music fans can catch the Boston Symphony...
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    Lenox, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Luxury Fox Hollow Laurel Lake Ranch1 / 16
    (1)Very good
    Lenox
    3.8 kilometres from Tanglewood
    4 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Lenox, Berkshires
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 11
    LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE1 / 19
    (1)Excellent
    Lenox
    3.8 kilometres from Tanglewood
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Mountain Views
    • Private Indoor Pool
    • Hot Tub
    • Air Conditioning
    • Sauna
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2017
    My wife booked this property for a couple of days for my birthday celebration. Howard is extremely accommodating the house came with everything! His employee Keith did...
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    About this property
    220+ Acres W\ Tennis Cts, Indoor / Outdoor Pool, Canoe, Fishing Boat, Hot Tub. New first time rental of 4 BR, 2BA, Cape Cod style, sleeps 10-12. New fully equipped kitchen w/ center island, indoor and outdoor barbecues, wine cooler, 2 fireplaces, large deck with 8 person hot tub and super seating...
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    Location Information
    Lenox, Berkshires
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
    The following rentals are within 10 kilometres of Lenox.
    To Ski or Not to Ski?  Great conditions Great fireplace.Your Choice.1 / 18
    (7)Excellent
    West Stockbridge
    4.8 kilometres from Tanglewood
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Wi-Fi
    • Balcony
    • Patio
    • Grill
    • Washer
    • Porch
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 September 2018
    The house was so comfortable; the location was perfect -- close to so many beautiful places and Berkshires attractions, especially Tanglewood!; Cassandra was so helpful when I...
    Reviewed 27 August 2016
    We had a wonderful stay in this large, lovely house that contained everything we needed for comfort and convenience. We were impressed with the degree to which details were...
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    About this property
    Enjoy this perfectly located home to pursue what brings you to the Berkshires. Ski and warm up next to the fire in the winter. Go to Kripalu but enjoy all the comforts of this home just 8 minutes away. Enjoy fabulous foods, and make new friends. Located in West Stockbridge minutes from everything ....
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    West Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Berkshire Farmhouse Vacation1 / 20
    (42)Excellent
    West Stockbridge
    6.6 kilometres from Tanglewood
    5 Bedrooms, 2 Bathrooms, Sleeps 15 Quick View
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    • Central Heating
    • Grill
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 December 2019
    We stayed in the Berkshire Farmhouse during our winter school break as a large group of 9 with adults and children (including teenagers). Very comfortable, clean, cozy and warm...
    Reviewed 23 September 2019
    We are 4 women in our 70's and 80"s who have been going away together for one week a year for the past 33 years. This year we decided to go to the Berkshires. The...
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    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,...
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    West Stockbridge, Berkshires
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 15
    Great Vacation House in the Berkshires by Richmond Pond1 / 10
    (4)Excellent
    Richmond
    6.8 kilometres from Tanglewood
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Grill
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2018
    Being Tanglewood lovers, this was the perfect vacation spot to enjoy the area's concerts, plays, art galleries and restaurants as well as the lovely Richmond Pond and the...
    Reviewed 28 August 2017
    This comfortable, breezy house was perfect! We loved being able to walk to the lake and canoe, play frisbee on the lawn, walk in the woods, eat on the deck, and gaze at the...
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    About this property
    Beautiful two bedroom house sits just steps from Richmond Pond. Enjoy a day on the water swimming and fishing followed by an evening enjoying the symphony at Tanglewood (ten scenic minutes away). Yoga enthusiasts will love the proximity to Kripalu (again, ten minutes away). Leaf peepers and skiers...
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    Richmond, Berkshires
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Comfortable Farmhouse in the Berkshires1 / 10
    (4)Excellent
    West Stockbridge
    4.8 kilometres from Tanglewood
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2017
    Nice house, great spot for our family reunion. Convenient to many of the Berkshires attractions. Nice kitchen for cooking and eating in for a group.
    Reviewed 6 June 2017
    House was comfortable and well furnished. The Berkshires are beautiful with lots of activities, galleries, shopping and restaurants. Our hosts were helpful and responsive to...
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    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....
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    West Stockbridge, Berkshires
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Lake House1 / 18
    (5)Very good
    Lee
    5.0 kilometres from Tanglewood
    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 2 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
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 9
    Berkshires Spacious Comfortable Charming Farmhouse1 / 12
    (2)Very good
    Lee
    6.4 kilometres from Tanglewood
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Washer
    • Wi-Fi
    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
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    West Stockbridge
    3.0 kilometres from Tanglewood
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living room, fall foliage and scenic atmosphere in the area, and soak in the...
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    West Stockbridge, Berkshires
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Cozy & Modern Home -mins from Tanglewood & Kripalu1 / 8
    (3)Excellent
    West Stockbridge
    2.6 kilometres from Tanglewood
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2019
    Great location - quiet, private, and felt like our own little home. Close to the lake with the beach. Only 4 minutes drive to Tanglewood.Next time I visit I will sure look to...
    Reviewed 18 December 2013
    We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
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    About this property
    Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living...
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    Location Information
    West Stockbridge, Berkshires
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Lee
    7.3 kilometres from Tanglewood
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Pet friendly
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    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 3-bedroom, 2-bathroom vacation rental house that comfortably sleeps 10! With new furnishings, a private...
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    Lee, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Richmond
    3.7 kilometres from Tanglewood
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Porch
    • Internet Access
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed...
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    Richmond, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Richmond
    7.2 kilometres from Tanglewood
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This is an exclusive Tentrr site. Tentrr partners with farmers, ranchers, and other property owners to offer unique outdoor accommodations on beautiful private land. Each Tentrr Signature site includes a 10'x12' safari-style canvas tent on a raised platform, and you'll find a queen-size single or...
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    Richmond, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Lee
    5.3 kilometres from Tanglewood
    4 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 15
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