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Pet Friendly Holiday Rentals in Berkshires

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    Travellers to Berkshires are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    40 Matching Rentals in BerkshiresView all 135 rentals
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    Cultural Playground 2 bed, 5 minutes to Tanglewood1 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Romantic Berkshire Cottage on Storybook Estate1 / 10
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Writer's Room at Chestnut Lodge1 / 8
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    2200sf Country House on 16 Acres-2 Miles to Jiminy1 / 14
    (3)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Mountain Views
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Internet Access
    • Central Heating
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and enjoy our beautiful mountain retreat - A home for every season. This charming home away from home is a wonderful place for family, friends and romance. Only 3 minutes from Jiminy Peak! With over 2200 square feet, this new country home has plenty of space for everyone yet a very cozy...
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    Hancock, Berkshires 001237
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Berkshire Farmhouse Vacation1 / 20
    (36)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • Grill
    • Internet Access
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 February 2018
    We had a large group staying at the house with kids and had a great experience. Elaine is very thoughtful, helpful and attentive. She obviously cares about the house and makes...
    Reviewed 15 November 2017
    Elaine was a pleasure to communicate with and made us feel right at home. The home is just how it looks in the pictures. If you're searching for a comfortable, clean, and cozy...
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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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    The Playhouse: 7,000 Sq Feet of Berkshires Luxury1 / 21
    (4)Excellent
    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 30 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 22 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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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Grill
    • Wi-Fi
    • Parking
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE ESCAPE at Stockbridge. Enjoy our Open & Spacious Newly built house in the Berkshires, Complete Privacy! No Visible Neighbors. -1 1/2 miles to downtown Stockbridge, -just minutes to Norman Rockwell museum, Chesterwood, Naumkeag, Tanglewood & Kripalu. -Housatonic River just across the street,...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Jacob's Tanglewood Ranch (great for groups 10+)1 / 22
    (2)Excellent
    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 28 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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    Tranquil 3BR Stockbridge House w/Private Deck1 / 30
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Internet Access
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2017
    The degree of care of the owners to assure a pleasant experience was incredible! There was a many page guide to the house, the property and the surrounding area. It...
    Reviewed 24 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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    Escape to the Berkshires!1 / 32
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2016
    My family and friends - group of 8 just spent an amazing week at this home. The house was a perfect size, clean and fully stocked. We made gourmet breakfasts, lunches &amp...
    Reviewed 15 May 2016
    The Levy's home was perfect for our intergenerational family, including a 7month old grandaughter. We were pleasantly surprised by how well the home was supplied and organized...
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    About this property
    Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. We are located close to Lenox, Stockbridge, Lee, Great Barrington and more. Our 3400 square foot ranch home is located in the heart of the Berkshires awaiting memorable times with your family and friends. Our...
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    Becket, Berkshires 01223
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Short Walk to Lake, Peaceful Getaway, Scenic Views1 / 13
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Grill
    • Central Heating
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Housekeeping Included
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2017
    The rental was spacious, immaculate and very comfortable and it's situated in a very private and relaxing part of the forest.
    Reviewed 25 July 2017
    Just what the doctor ordered. Beautiful, peaceful getaway in a lovely private community. Comfortable beds, great kitchen, would DEFINITELY stay again.
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    About this property
    Would you like to spend some time in our cozy retreat in the Berkshires? Our three-bedrooms, two bathrooms house is located in a private community, in the middle of the Tolland state forest , surrounded by the woods and lakes, but at the same time close to major attractions. Fully renovated, the...
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    Granville, Berkshires 01034
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Casa Uccello1 / 15
    (3)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
    • Air Conditioning
    • Washer
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Mountain Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 February 2018
    Great house, with plenty of space (for 2 families and 2 dogs) and many nice touches from the fireplaces with well-stocked firewood to the coffee makers to a heated toilet seat...
    Reviewed 29 November 2017
    The house was perfect for our large group. We cooked and ate outside almost every meal. The fire pit and river were the highlights. We will be back again!
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    About this property
    Tranquil river front historic farmhouse, 200 years old, with a touch of modern decor. Great for large groups and multiple families. 10 minutes from Great Barrington & Butternut, 20 minutes from Tanglewood. Salt Water Hot Tub, Outdoor fire pit, 2 indoor fireplaces. projector. TV. Wii. Entertaining...
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    New Marlborough, Berkshires 01244
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Heart of the Berkshires!1 / 12
    (2)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2017
    A friend and I rented this charming home for 3 nights. It was immaculate, the kitchen was well stocked, furniture/beds comfortable. The bedrooms had window a/c units. What...
    Reviewed 30 June 2017
    I was looking for a place for two couples for a weekend in the Berkshires, and stayed at this house. It was a perfect fit for my needs. The house is on a road that has very...
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    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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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
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    Suitability
    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 01266
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Lake House in the Berkshires1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Patio
    • Grill
    • Balcony
    • Parking
    • DVD Player
    • Air Conditioning
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 October 2015
    It's my first time booking through flipkey. Zoe, the hostess, helped me a lot during the process. She is warm, kind, and patient. Her email was in details and we checked in...
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    About this property
    Enjoy beautiful Prospect Lake while staying at our comfortable home. Full kitchen with almost anything you can think of. Farm table seats 8 and is perfect for family meal. Cozy living spaces with enough seating for all to gather. Sunny bright deck in private rear yard . Covered porch is perfect...
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    North Egremont, Berkshires 01230
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    • 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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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE1 / 19
    (1)Excellent
    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 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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    Lenox, Berkshires 01240
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Berkshires Waterfront Lakehouse Sanctuary1 / 24
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 November 2017
    We spent two nights here on short notice and couldn’t have been happier with everything. This is a home done right - it’s homey and perfectly furnished and oh-so-cozy. Quaint...
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    About this property
    Beautiful private peninsula like setting surrounded by a cove , stream and lake adorn this location. Waterfowl and birds are everywhere in this quiet spot just a few minute walk from the 11 mile Ashuwilticook Rail Trail. The house has undergone a total renovation and all the furnishings are new...
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    Lanesboro, Berkshires 01224
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxury Fox Hollow Laurel Lake Ranch1 / 16
    (1)Very good
    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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • DVD Player
    • Central Heating
    • Terrace
    • Balcony
    • Housekeeping Included
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Secluded high on a mountainside and surrounded by thousands of acres of state park and conservation land, The Pod is a rustic early 1970's timber and glass octagon set on a concrete pedestal. Decks on four sides with forest or distant mountain views. One stream runs within 15 feet of the master...
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    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 01254
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Grill
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Garden
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **1 week minimum July & August** Just 1 1/2 to the Red Lion Inn in Downtown Stockbridge, Tanglewood, Norman Rockwell Museum, Private country setting just across from the Housaitonic River. Our newly built home pairs a traditional shingle style exterior with an open & slightly modern interior. The...
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    Stockbridge, Berkshires 01262
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Air Conditioning
    • Parking
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located along the Appalachian trail and 3 miles to Great Barrington, this designer home is central to all the Berkshires has to offer, not to mention being 35 minutes to Hudson you are really in the center of of it all. This completely separate designer home is located on the 2nd and 3rd floors...
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    Sheffield, Berkshires 01257
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Unique People & Pet-Welcoming Country Haven1 / 37
    (165)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Outdoor Dining Area
    • Air Conditioning
    • Shared Garden
    • Cable/satellite TV
    • Washer
    • Secure Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 days ago
    Patricia's cottage is in a great location for hiking, biking, skiing and exploring in hills along the Mohawk Trail, just a few minutes from lovely Shelburne Falls, and within...
    Reviewed 2 weeks ago
    My partner and I stayed here with our 1.5 y/o rescue. Our rescue, Ollie, is very timid and anxious but he felt very relaxed at the cottage. Our plan was to have a nice getaway...
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    About this property
    Discover Cavalier Cottage B&B, a pet-friendly home away from your home and an attractive alternative to conventional hotels, motels and B&B’s. We warmly welcome visitors who come to this beautiful area of Western Massachusetts with or without their companion animals. Now in its sixth year,...
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    Charlemont, Berkshires 01339
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Lakefront Berkshires Ski/Summer House, Great Views1 / 17
    (4)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Cable/satellite TV
    • Internet Access
    • Mountain Views
    • Grill
    • DVD Player
    • Waterfront
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 November 2017
    The house was cozy. The lake was beautiful. The surrounding towns offer great restaurants. The host was very helpful.
    Reviewed 17 November 2017
    We rented this lovely home on the lake (or maybe it's a pond... Long Pond I think) last year and loved every minute of our visit. The house is well equipped and has all one...
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    About this property
    Located in a wooded area overlooking a pristine lake, this woodsy style contemporary is a sportsman's paradise. It's a short drive to skiing (Jiminy Peak, Butternut, Catamount) and cultural attractions, (Tanglewood, National Music Center, Aston Magna, etc.) or you can fish, swim, boat, hike, or...
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    Great Barrington, Berkshires 01236
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Berkshires House, 40 wooded acres, Lake Frontage1 / 16
    (20)Very good
    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 December 2017
    Karl and his place are supremely magical. The cottage is nestled in the woods on activated lands with a beautiful comforting peaceful lake, nature trails, less than an hour from...
    Reviewed 22 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...
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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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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
    • Hot Tub
    • Parking
    • Wi-Fi
    • Grill
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the beautiful Berkshires. Watch the horses roam. Have a guided trail ride (additional fee) or have a camp fire only feet away from the horses. Within steps from your accommodations, enjoy the largest recreational lake in Massachusetts. Bring your boat or jetski. Or use our row boat. Go...
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    Location Information
    East Otis, Berkshires 01029
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Parking
    • Mountain Views
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf. The Space: Quaint cottage with wood burning stove. Ideal base for enjoying...
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    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Apartment walking distance to Mass MoCa!!1 / 22
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Skiing: Property Is In A Ski Resort
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 September 2015
    Owners were very friendly and helpful. We enjoyed our stay very much. this is the place for a quiet vacation.
    Reviewed 7 July 2014
    Stephanie was helpful and accommodating of us and our last minute request . Sheafs it easy to stay, come and go and we found the location convenient yet private and remote from...
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    About this property
    I have a 2 to 3 bedroom first floor apartment located in a dead end street. This spacious 8 room apartment is surrounded by woods and minutes from downtown North Adams or Williamstown!! It is also walking distance to Mass MoCa (about a 10 minute walk)!!! Animals are welcome if needed. The master...
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    Location Information
    North Adams, Berkshires 01247
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 10
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    3 Bedrooms, 1 Bathroom, Sleeps 15 Quick View
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    • Patio
    • DVD Player
    • Central Heating
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is located at the end of a dead end street. It has a huge, private backyard with 2 firepits, hammock, portable bar, grill and ample seating. Under one mile to downtown North Adams and about a 5 minute drive to Williamstown. This is a 3 bedroom, upstairs apartment (one bedroom has a...
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    North Adams, Berkshires 01247
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 15
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    Serene Lakefront Cottage1 / 17
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2016
    We stayed for a week with two teenaged boys and two dogs. We had a wonderful time. The lake was fully accessible and the boats and life vests well cared for. The photos are...
    Reviewed 2 September 2015
    My husband and I plus our two dogs recently took one last family vacation before our first son arrives later this year. We were looking for a private and peaceful place where we...
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    About this property
    Pretty cottage in the woods on a beautiful clean private lake with a stream running through the property's two acres of land. Newly constructed, spacious and sunny second floor with views of the lake. Hardwood floors throughout the house. Swim, kayak, canoe (both supplied with life vests) or...
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    Becket, Berkshires 01223
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Waterfront
    • Patio
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring your loved one along on a Berkshires getaway in this 1-bedroom, 1-bathroom vacation rental cottage in New Marlborough that sleeps 2. Nestled under the pine trees on the edge of Lake Buel, you'll have unbeatable views of the picturesque landscape, framed by the large windows throughout the...
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    New Marlborough, Berkshires 01230
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    • Patio
    • Internet Access
    • DVD Player
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just over 2 hours from NYC and Boston sits our fully modern log cabin nestled within a private acre of natural forest in southern Berkshire County. Our classic post and beam log cabin has been updated with all of today's essentials like WiFi, cable TV, Netflix & HBO, Nest smart thermostat, open...
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    Sheffield, Berkshires 01257
    Cabin Holiday Rental - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Cozy and clean in Gt Barrington- 1 week in summer!1 / 10
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Outdoor Dining Area
    • DVD Player
    • Parking
    • Porch
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There are about twelve (12!) hiking...
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    Great Barrington, Berkshires 01230
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    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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    Stockbridge, Berkshires 01262
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Internet Access
    • Private Garden
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Stockbridge, Berkshires 01262
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    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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    Location Information
    Stockbridge, Berkshires 01262
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    • Washer
    • Central Heating
    • Housekeeping Included
    • Mountain Views
    • Internet Access
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our family home is close to museums (less than 2 miles to MoCA), state parks, hiking trails, skiing cultural events and colleges (Williams, MCLA). Enjoy the beauty of the Berkshires in the comfort of a large farm house with views of Mt Greylock. The 1st floor guest bedroom offers a queen bed with a...
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    Location Information
    Clarksburg, Berkshires 01247
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    9 Bedrooms, 8 Bathrooms, Sleeps 16 Quick View
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    • Grill
    • Patio
    • Wi-Fi
    • Washer
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is by far one of the nicest homes that you will come across in the area (or this site for that matter!). The estate comes complete with 7 bedroom, 7 bathroom main house, a guest house with 2 bedrooms and one bath, several fire places, a pool table, ping pong table, pool, jacuzzi, several TV's...
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    Location Information
    Great Barrington, Berkshires 01230
    Holiday Rental House - 9 Bedrooms, 8 Bathrooms, Sleeps 16
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