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East Chatham Holiday Rentals

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    East Chatham
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    East Chatham
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    East Chatham
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    East Chatham
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Hot Tub
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    • Satellite TV
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    Pet friendly
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    East Chatham, New York 12060
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    East Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
    • Washer
    • Sauna
    • Patio
    • Air Conditioning
    • Internet Access
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    East Chatham, New York 12136
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    The following rentals are within 25 kilometres of East Chatham.
    Beautiful New Construction Vacation Home1 / 32
    (5)Excellent
    Stockbridge, MA
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Sauna
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2017
    Our 4 families stayed here for a long ski weekend and had the best time! The home is beautiful-- and had plenty of space for all of us! The home was fully stocked with...
    Reviewed 9 November 2016
    Excellent experience. Very spacious and beautiful. Amazing backyard woods. Beautiful scenery within and around the town. Very attentive owners.
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    About this property
    We call this house ‘South Sedgwick’ because of its location on a piece of land formerly used by the Sedgwick family for picnicking–an ideal spot for relaxation with stunning views of Monument Mountain and Ice Glen. The house is newly constructed with ash hardwood floors, custom white pine trim and...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Cultural Playground 2 bed, 5 minutes to Tanglewood1 / 25
    (1)Excellent
    Stockbridge, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Parking
    • Patio
    • Grill
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 November 2016
    Me & my son Josh had a lovely stay at the cottage. Ruth was very pleasant, the place was clean and the location was perfect. We were provided with wood for fire, the kitchen...
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    About this property
    This 1600 sq. ft. cottage boasts everything you would need for your visit to the Berkshires whether it be for a full summer / winter season to explore this beautiful area or a quick getaway to Tanglewood, The recently added master suite features a queen size bed, en-suite bathroom and a bonus...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Berkshire Farmhouse Vacation1 / 20
    (27)Excellent
    West Stockbridge, MA
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 days ago
    This lovely place was home for us for a weekend in June. Our group of six fit nicely in this charming home with plenty of room to spare. The kitchen worked perfectly for our...
    Reviewed 17 May 2017
    We enjoyed our stay tremendously. The house is beautiful, very well equipped, spacious and very comfortable. Elaine is so kind and friendly and helped us with all our needs. 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 01266
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Lenox, MA
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Private Garden
    • Patio
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Lenox, Berkshires 01240
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Family-friendly Cottage Near Lake, Tanglewood1 / 16
    (5)Excellent
    Stockbridge, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Satellite TV
    • Porch
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    • Washer
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 24 October 2013
    Some friends and I wanted to have a reunion as we are spread out along the east coast, and we were debating between camping or renting. I heard no end of the gratitude from my...
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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 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Stockbridge, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
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    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Stockbridge, Berkshires 01238
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Lenox, MA
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Garden
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This sophisticated ranch is privately sited on a premier road in Stockbridge. Less than a mile to Tanglewood, Stockbridge Bowl, and local theatre companies. Nestled between Lenox and Stockbridge, this is perfect location for your vacation. 3 bedroom and 1 bath, an open floor plan with the guest...
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    Lenox, Berkshires 01240
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Berkshire's Getaway ---Peace & Tranquility1 / 20
    (3)Excellent
    Pittsfield, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Grill
    • Washer
    • Satellite TV
    • Air Conditioning
    • Mountain Views
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 May 2017
    My family stayed here for 4 nights in April. The house is a small cape cod style home but well very maintained. The layout is 1 bedroom on the first floor and 2 bedrooms on...
    Reviewed 31 May 2016
    This home is meticulous, charming, cozy, comfortable and relaxing. We thoroughly enjoyed the backyard and spent hours just visiting with each other over a warm fire while the...
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    About this property
    House is very private and located on 4 acres of Land. Back yard is peaceful and overlooks ponds. The backyard has a patio/picnic area with gas grill and firepit. One of the ponds has a spurting and lighted fountain that is relaxing ...so have a campfire at night and watch the lighted fountain for a...
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    Pittsfield, Berkshires 01201
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Lenox, MA
    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 01240
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 11
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    Comfortable Farmhouse in the Berkshires1 / 10
    (2)Excellent
    West Stockbridge, MA
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    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...
    Reviewed 18 October 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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    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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    Location Information
    West Stockbridge, Berkshires 01266
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Tranquil 3BR Stockbridge House w/Private Deck1 / 30
    (1)Excellent
    Stockbridge, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 October 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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    About this property
    Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house, which sleeps 6 and boasts a private deck. Nestled within the serene forests of the Berkshires, ‘The Redway House’ is the quintessential setting for your next Massachusetts retreat. THE PROPERTY...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cozy & Modern Home -mins from Tanglewood & Kripalu1 / 8
    (2)Excellent
    West Stockbridge, MA
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    West Stockbridge, Berkshires 01266
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Restored 1886 Eyebrow Colonial1 / 17
    (1)Excellent
    Stockbridge, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Patio
    • Air Conditioning
    • Internet Access
    • Grill
    • Washer
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 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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    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...
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    Location Information
    Stockbridge, Berkshires 01262
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coxsackie
    6 Bedrooms, 3 Bathrooms, Sleeps 25 Quick View
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    • Satellite TV
    • Waterfront
    • Patio
    • Air Conditioning
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    • Internet Access
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Hudson Hideaway is an inviting 6 Bedroom home with its own private beach in a quiet residential neighborhood. Sun yourself on our private dock or take a dip in the Hudson River to cool off. Relax at night on the back patio overlooking the river while a cozy fire blazes in the new outdoor brick...
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    Coxsackie, New York 12051
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 25
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    Philmont
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Secure Parking
    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    Located in the center of Columbia County, NY this retreat is a great spring board to all it has to offer: minutes to Hudson, Chatham, High Falls, hiking trails, farms, streams. You’ll love the varied bright cozy rooms to lounge in, including a screened front porch. Most relaxing is to hang out on...
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    Philmont, New York 12534
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Stockbridge Bowl house1 / 11
    (4)Average
    Stockbridge, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Central Heating
    • Internet Access
    • Washer
    • Satellite TV
    • Mountain Views
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 July 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...
    Reviewed 14 July 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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    About this property
    3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard.
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    Location Information
    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Berkshire Blueberry Lodge LLC - Near Jiminy Peak1 / 24
    (6)Excellent
    Stephentown
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Mountain Views
    • Wi-Fi
    • Grill
    • DVD Player
    • Outdoor Dining Area
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2016
    My siblings and I (8 adults total) spent a wonderful weekend at the Blueberry Lodge. Most of our time was spent at the lodge except for an afternoon and evening attending the...
    Reviewed 8 March 2016
    My girlfriends and I have been going on yearly ski trips primarily in NH, VT, and ME for the past 29 years. This year we decided to try the Berkshires, for some place different...
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    About this property
    Countryside setting with a fantastic view of the Berkshires and centrally located. 10 minutes to Jiminy Peak ski area, 30 minutes to Tanglewood, 25 minutes to Stockbridge, 20 minutes to Mt. Greylock, 25 minutes to Williamstown theater. the lodge has a 400 square foot grand room for parties,...
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    Location Information
    Stephentown, New York 12168
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE1 / 25
    (1)Excellent
    Lenox, MA
    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
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 weeks ago
    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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    Lenox, Berkshires 01240
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Enjoy Summer in The Berkshires1 / 20
    (6)Excellent
    West Stockbridge, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Wi-Fi
    • Balcony
    • Patio
    • Grill
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    • Porch
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 2 November 2014
    Had an outstanding couple of weeks staying here; place was quiet, peaceful and not too far from civilization. All the amenities and space you could wish for and Cassandra and...
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    About this property
    Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private. Visit our web-site aberkshirehome. The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting. It is...
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    Location Information
    West Stockbridge, Berkshires 01266
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Lenox, MA
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Satellite TV
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    • Mountain Views
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just steps to Tanglewood Main Gate and Kripalu from this dramatic three-story shingle style contemporary with five bedrooms and five and a half baths. The six hundred square foot great room has a soaring ceiling, fireplace, interior balcony, and multiple French doors and windows to overlook the...
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    Location Information
    Lenox, Berkshires 01240
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    Lenox, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    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 01240
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Lenox, MA
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    Great little house in a very convenient location. Set nicely back from the street with a spacious back and side yard. 8 minutes drive to tanglewood. All rooms are furnished. Living room with bay window and fireplace, hardwood floors throughout. Almost an acre of land with large trees and garden....
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    Lenox, Berkshires 01240
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Spencertown
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Frank Lloyd Wright-inspired retreat is the perfect country escape for city dwellers. Set on 30 private acres with trails for hiking and a lake, this professionally decorated home blends rustic charm with modernity. There are two bedrooms, one with a fireplace, two bathrooms, plus a sleeping...
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    Spencertown, New York 12165
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gartner House, a charming home in Lenox1 / 21
    (25)Excellent
    Lenox, MA
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Porch
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    • Internet Access
    • Central Heating
    • Grill
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 February 2017
    My teenage daughters, one of their friends and I booked this house for a long weekend getaway. It was just right for us. There were 4 of us, but if we had a couple of more we...
    Reviewed 19 January 2017
    This is the second time my girlfriends and I stayed at Gartner House and we found it just as lovely this time as last. We like staying in to catch up and cook and the house is...
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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 01240
    Condo/Apartment - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    Stockbridge, MA
    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...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Berkshire Mountain Lodge - Fri, Sat,Sun check ins only!  Inbox x1 / 5
    (2)Very good
    Pittsfield, MA
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 1 week ago
    We Loved the Berkshire Mountain Lodge. Just got back yesterday. We stayed for seven nights. It is quiet as all the rooms consist of one bedroom, living room, large bathroom and...
    Reviewed 26 April 2017
    This timeshare was just what we wanted. Good location to fun activities and restaurants in the Berkshires. They have a large indoor heated pool, gym, game room. Every day...
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    About this property
    We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays, and Sundays only. Located near Lenox, Massachusetts and among the picturesque Berkshire highlands lies the Berkshire Mountain Lodge. Ideal no matter the season, Berkshire Mountain Lodge offers a...
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    Pittsfield, Berkshires 01201
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Stunning New Construction All SeasonLakefront Home1 / 25
    (3)Very good
    Valatie
    3 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Porch
    • Satellite TV
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning New Lakefront Home Near Berkshires with Gourmet Kitchen, large expansive views of Kinderhook Lake. All the bells and whistles including a TV in the Master Bathroom and a whole house stereo system. This home is an air conditioned, upscale Craftsman- styled cottage with 75 feet of lakefront...
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    Valatie, New York 12184
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 5
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    Pittsfield, MA
    7 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    • Central Heating
    • Grill
    • Terrace
    • Washer
    • Balcony
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    • Hot Tub
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a beautiful 7 bedroom home with over 4000 sq. ft. of nicely furnished large rooms. Nestled in the heart of the Berkshire Mountains, between 2 lakes and located in a quiet family friendly neighborhood. Just minutes from the New York border. Our home is a fantastic deal for the wonderfully...
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    Pittsfield, Berkshires 01201
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 18
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    Stockbridge, MA
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Private Garden
    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Stockbridge, Berkshires 01262
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Stockbridge, MA
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    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....
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    Location Information
    Stockbridge, Berkshires 01262
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Heart of Lenox1 / 10
    (1)Excellent
    Lenox, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    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 01240
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Stockbridge, MA
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Internet Access
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    Pet friendly
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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...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Stockbridge, MA
    8 Bedrooms, 10 Bathrooms, Sleeps 17 Quick View
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    • Satellite TV
    • Private Garden
    • Wi-Fi
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    • Secure Parking
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Stockbridge MA Bed & Breakfast is the closest Inn and within walking distance to the Norman Rockwell and Chesterwood Museums. Nestled on 4 private acres of Berkshires landscape, we offer top quality B&B lodging accommodations that is centrally located to all major area attractions. A Federal...
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    Stockbridge, Berkshires 01262
    Private Room - 8 Bedrooms, 10 Bathrooms, Sleeps 17
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    Stockbridge, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
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    Pet friendly
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    Smoking allowed
    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...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Hudson Valley Cottage1 / 13
    (1)Excellent
    Ghent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Mountain Views
    • Satellite TV
    • Patio
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    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2013
    This was the perfect location for a base camp from which to explore the Hudson River Valley area. We took in a Tanglewood concert (40-minute drive) and explored the backroads...
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    About this property
    Enjoy a newly renovated and furnished, one bedroom guest cottage, in an enchanting and quiet area. Located behind a stone castle on a 2 1/2 acre park-like property it's a beautiful place to vacation. You also have access to a large 6 person hot tub and all the deck areas.<BR><BR>The bedroom and...
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    Ghent, New York 12075
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Ghent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will be enjoying a newly renovated space with Calcutta marble floors throughout. The house features 2 bedrooms at opposite sides of the house to provide more privacy. A luxurious bathroom with a Roman soaking tub and marble mosaics. A totally loaded kitchen and great outdoor space which...
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    Ghent, New York 12075
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Chatham
    4 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Patio
    • Terrace
    • Housekeeping Included
    • Balcony
    • Central Heating
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully renovated 1800s farm house on 100 acres with heated in ground gunnite pool, hiking trails located on a beautiful creek. We also have a guest house with two more bedrooms and a full kitchen by the pool that is perfect for bringing your in-laws or babysitter. The house has a chef's kitchen...
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    Chatham, New York 12037
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 6
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    West Stockbridge, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Washer
    • Balcony
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    • Housekeeping Included
    • Mountain Views
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We offer two bedrooms accessible via a private staircase in our recently renovated Victorian farm house located on two beautifully landscaped acres with seasonal gardens and adjoining woods and fields. Each bedroom sleeps 2; they can be booked individually or together at $105/bedroom/night. We...
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    Location Information
    West Stockbridge, Berkshires 01266
    Private Room - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    West Stockbridge, MA
    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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    Location Information
    West Stockbridge, Berkshires 01266
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Coxsackie
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Hudson estate is nestled on 31 acres of beautiful park-like splendor, this graceful Victorian manor house offers every possible convenience, including a heated infinity pool and spa with outdoor shower, billiard room, media room, solarium dining area with hand-painted murals, and so much...
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    Coxsackie, New York 12015
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Kinderhook
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Private Garden
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    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Conveniently located for your next Hudson Valley Wine Tour or Relaxing Hudson Valley Bed and Breakfast Hotel Lodging Get-a-way with an Organic Farm to Table Breakfast! Mile Hill B and B, c.1852, is an original jewel with an interesting history. This is a newly renovated Colonial Farm House; two...
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    Kinderhook, New York 12106
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Stephentown
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Mountain Views
    • Satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two story cape that can sleep up to 12 people on 50 acres. Fully equipped kitchen, laundry area and dining & living room that faces the Berkshire Mountains. Relaxingy deck with barbecue. Walking trails and swimming pond make it a perfect getaway place. Wifi, a/c tv Near all Berkshire attractions,...
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    Location Information
    Stephentown, New York 12168
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Lenox, MA
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Fully Furnished and newly renovated condo in beautiful town center of Lenox, Mass. Walk to world class restaurants and be only a short distance from many outdoor activities. Condo is fully furnished with all new furniture . Includes gas fireplace, central AC and heat, Cable and wireless internet...
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    Location Information
    Lenox, Berkshires 01240
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stockbridge, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    • Satellite TV
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    • Air Conditioning
    • Patio
    • Grill
    Suitability
    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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    Location Information
    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Stephentown
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    • Grill
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect weekend retreat or short term furnished rental close to all Berkshire, MA amenities and Jiminy Peak Mountain Resort, museums, theatre, restaurants, shopping and more! 20 Minutes to Williamstown, 25 to Pittsfield, 30 to Albany. Home is efficient, easily maintained in an adorable 1870's...
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    Location Information
    Stephentown, New York 12168
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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