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Holiday Rentals near October Mountain State Forest

317 Woodland Rd, Lee, Massachusetts 01238-9219
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    Travellers to Lee are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    All 37 Rentals in Lee
    Berkshires Spacious Comfortable Charming Farmhouse1 / 12
    (2)Very good
    1.5 kilometres from October Mountain State Forest
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Lake House1 / 18
    (5)Very good
    2.6 kilometres from October Mountain State Forest
    5 Bedrooms, 6 Bathrooms, Sleeps 9 Quick View
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    7.6 kilometres from October Mountain State Forest
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    6.3 kilometres from October Mountain State Forest
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    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
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    2.3 kilometres from October Mountain State Forest
    4 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    • Washer
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    Pet friendly
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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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 15
    Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!1 / 31
    (50)Excellent
    4.1 kilometres from October Mountain State Forest
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Lee, Berkshires
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
    Lovingly restored Victorian in Lee's Historic District **Spring:3rd nt 1/2 off1 / 33
    (85)Excellent
    4.1 kilometres from October Mountain State Forest
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Lee, Berkshires
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Elegant 19th Century New England Newly Renovated 1BR Vacation Rental1 / 12
    (38)Very good
    3.5 kilometres from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Lee, Berkshires
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedroom newly renovated townehouse, beautifully decorated at Garfield House1 / 15
    (12)Excellent
    3.5 kilometres from October Mountain State Forest
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lee, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite1 / 50
    (6)Excellent
    3.5 kilometres from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Lee, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3.8 kilometres from October Mountain State Forest
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Lee, Berkshires
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 14
    1.1 kilometres from October Mountain State Forest
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Lee, Berkshires
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    Lovely Lakefront Cottage, Peaceful Setting, Hiking And More1 / 20
    (10)Excellent
    7.5 kilometres from October Mountain State Forest
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
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    Lee, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    The Freckled Hen's Berkshire Nest1 / 19
    (28)Excellent
    3.1 kilometres from October Mountain State Forest
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lee, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    6.6 kilometres from October Mountain State Forest
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful home that located between Lenox and Stockbridge. Minutes from Downtown Lee, Stockbridge and Lenox. Large nice yard, two car Garage and plenty of parking. Home offers an open floor plan for the kitchen and living room along with four bedrooms, and two full bathrooms. There is a State...
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    Lee, Berkshires
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
    Romantic Boutique Hotel / Bed and Breakfast - Deluxe Firespa Suite1 / 50
    (3)Excellent
    3.5 kilometres from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lee, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Romantic Boutique Hotel / Bed and Breakfast - Standard King With Gas Fireplace a1 / 47
    (9)Very good
    3.5 kilometres from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lee, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Elegant 19th Century New England 2BR Vacation Rental at Garfield House1 / 21
    (52)Excellent
    4.0 kilometres from October Mountain State Forest
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Lee, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible1 / 50
    (8)Excellent
    3.5 kilometres from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Lee, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Romantic Boutique Hotel / Bed and Breakfast - SchoolHouse Suite1 / 50
    (8)Excellent
    3.5 kilometres from October Mountain State Forest
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Lee, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Charming 1860 Farmhouse, Completely Renovated, Convenient Location, Central AC1 / 22
    (29)Excellent
    3.6 kilometres from October Mountain State Forest
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Lee, Berkshires
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Garfield House Studio at 2081 / 16
    (4)Excellent
    3.3 kilometres from October Mountain State Forest
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Lee, Berkshires
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Gartner House, a charming home in Lenox1 / 21
    (35)Excellent
    4.3 kilometres from October Mountain State Forest
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Porch
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 October 2020
    Our stay at Gartner House was great. It is steps away from the heart of Lennox which has a handful of charming, good restaurants, shops, etc. It is also, clearly, a home and...
    Reviewed 3 September 2020
    Just steps from picturesque downtown Lenox and an easy drive from Tanglewood, Kripalu, Norman Rockwell Museum, scenic lakes with swimming beaches, and more. This house has all...
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    About this property
    Located on a quiet side street in the charming Berkshire town of Lenox, Gartner House is a great place to call home while exploring this scenic, historical, and culturally rich area of Western Massachusetts. Walk to breakfast, lunch or dinner at one of the town's many charming restaurants, explore...
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    Lenox, Berkshires
    Condo/Apartment - 4 Bedrooms, 1 Bathroom, Sleeps 7
    8.0 kilometres from October Mountain State Forest
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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
    7.8 kilometres from October Mountain State Forest
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    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 19 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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    West Stockbridge, Berkshires
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Heart of Lenox1 / 7
    (2)Excellent
    4.4 kilometres from October Mountain State Forest
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
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    Pet friendly
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    Reviewed 15 August 2018
    1/2 house, with owners in other half, which was handy for questions and suggestions. Very clean, and queen bed was really comfortable. Other BR has twin bedsKitchen has...
    Reviewed 28 May 2017
    Title sums it up! Excellent choice for our recent visit to Lenox. The house is very clean and comfortable and the owners are very accommodating. Location is great, just steps...
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    About this property
    Just rated Best Small Town in the Northeast by USA Today, our home is located in the heart of Lenox MA! Come relax in our lovely home, situated in a quiet neighborhood just steps from downtown. Walk to Zagat rated restaurants, shop unique boutique shops, hike in Kennedy Park. Whether you love the...
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    Lenox, Berkshires
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Family-friendly Cottage Near Lake, Tanglewood1 / 16
    (6)Excellent
    6.5 kilometres from October Mountain State Forest
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
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    Reviewed 22 August 2017
    Location was fantastic. Sarah (the owner) provided some great advice on local farmers markets and hikes. The beach was a quick walk from the cottage where we could paddle on...
    Reviewed 31 July 2015
    This was a wonderful place to spend a family vacation. The house is immaculate, functional and well furnished. The proximity to all of the many venues and activities the area...
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    About this property
    Located a short walk to the town beach on the Stockbridge Bowl, and 1.5 miles from Tanglewood's Hawthorn entrance, this casual summer cottage is a great get away for the whole family. The master bedroom is equipped with a queen bed; two twins in the 2nd bedroom, and a full-size bed in the 3rd...
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    Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    7.6 kilometres from October Mountain State Forest
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS CUSTOM BUILT HOME is a one-of-a-kind, must see getaway retreat that is beautifully furnished, and meticulously maintained. The entire first floor 'guest suite' was designed to accommodate friends or extended family. The upper level is the main floor with an open plan kitchen, dining room, and...
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    Stockbridge, Berkshires
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    4.4 kilometres from October Mountain State Forest
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    This fully private 3-bedroom, 2.5-bath house is nestled in the heart of historic downtown Lenox - central to all the attractions in the Berkshires, including world-class arts and culture, outdoor recreation, museums, shops, and restaurants! Newly designed and furnished in 2021, this warm and...
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    Lenox, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    4.9 kilometres from October Mountain State Forest
    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
    3.5 kilometres from October Mountain State Forest
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    19 Century New England classic home renovated to maintain is historical look and feel but with modern kitchen and bathrooms
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    Lee, Maine
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Berkshires Home w/Kayak - Walk to Stockbridge Bowl1 / 24
    (1)Very good
    6.7 kilometres from October Mountain State Forest
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Skiing: Property Is In A Ski Resort
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    Pet friendly
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    Smoking allowed
    Reviewed 22 February 2021
    This house was cozy, with a big fireplace, comfy seating, and many places to sleep. We stayed during the winter and it was an easy drive to Ski Butternut. If you stayed during...
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    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
    6.5 kilometres from October Mountain State Forest
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Skiing: Property Is In A Ski Resort
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    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 6
    Fox Hollow Laurel Lake Ranch1 / 16
    (1)Very good
    4.1 kilometres from October Mountain State Forest
    4 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    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
    6.7 kilometres from October Mountain State Forest
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Escape to the serene beauty of the Berkshires and stay at this bright and cozy 2-bed, 2-bath cabin! Nestled just a few steps from the Stockbridge Town Beach, the vacation rental is perfectly located for enjoying the area's top attractions, like lake activities, Tanglewood, the Norman Rockwell...
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    West Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    5.8 kilometres from October Mountain State Forest
    3 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wheel chair accessible front and back by built-in ramps, not ADA compliant. Spectacular Berkshire Location, 2 minute walk to Tanglewood. Fabulous great room, high-end kitchen, dining area and bedrooms. 3 Fireplaces. Large outdoor pool, attached hot tub. Across from Stockbridge Bowl Lake with shared...
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    Location Information
    Stockbridge, Berkshires
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 8
    LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE1 / 19
    (1)Excellent
    4.0 kilometres from October Mountain State Forest
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • 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 26 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
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