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Pet Friendly Holiday Rentals in Pittsfield

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    Don't let other travellers get your favourite Pittsfield area holiday rental. You're so close to securing your perfect getaway. Book today.
    13 Matching Rentals in the Pittsfield AreaView all 70 rentals
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    The following rentals are within 15 kilometers of Pittsfield.
    2200sf Country House on 16 Acres-2 Miles to Jiminy1 / 14
    (3)Very good
    Hancock
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Berkshire Farmhouse Vacation1 / 20
    (36)Excellent
    West Stockbridge
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Writer's Room at Chestnut Lodge1 / 8
    (1)Excellent
    Lee
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    The Playhouse: 7,000 Sq Feet of Berkshires Luxury1 / 21
    (4)Excellent
    Lee
    6 Bedrooms, 5 Bathrooms, Sleeps 26 Quick View
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    Amenities & Details
    • Private Garden
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 April 2017
    First impressions were that it was amazing as the description - real wow factor. Equipped with everything you could want. The socialising space was amazing, with room for all 19...
    Reviewed 21 December 2016
    The Playhouse provides all that is necessary to have a fabulous time with family or a large group. I have looked for a place to hold our annual family Christmas gathering for...
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    About this property
    220 acres with yoga studio and lakefront. Built by Westinghouse and then part of the Vanderbilt Estate, The Playhouse is a newly renovated iconic Berkshire's property that once served as a theater space for America's greatest innovators, and is now hung with fine art, and includes an in-house yoga...
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    Lee, Berkshires 01238
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 26
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    Jacob's Tanglewood Ranch (great for groups 10+)1 / 22
    (2)Excellent
    Lee
    5 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    Amenities & Details
    • Wi-Fi
    • Porch
    • Air Conditioning
    • Balcony
    • Washer
    • Mountain Views
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2017
    Excellent location to enjoy the best of the Berkshires, and a comfortable, spacious house full of historic character. 3 wood burning fireplaces and a screened porch make this...
    Reviewed 30 May 2016
    My family loved this house - parents and kids, all found it comfortable, spacious, and welcoming. Host is accommodative on last-minute changes or special requests. Easy...
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    About this property
    In the heart of the Berkshires: near Tanglewood, Jacob's Pillow, Jiminy Peak, Ski Butternut, Lenox MA, Stockbridge MA. Completely restored historic house with fully equipped kitchen, 5 bedrooms (each with a private bathroom), 3 spacious common rooms. A comfortable place for a family reunion,...
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    Lee, Berkshires 01238
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 20
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    West Stockbridge
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    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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    Luxury Fox Hollow Laurel Lake Ranch1 / 16
    (1)Very good
    Lenox
    4 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Washer
    Suitability
    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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    Heart of the Berkshires!1 / 12
    (2)Very good
    Lenox
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 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 29 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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    Berkshires Waterfront Lakehouse Sanctuary1 / 24
    (1)Excellent
    Lanesboro
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 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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    Richmond
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE1 / 19
    (1)Excellent
    Lenox
    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 25 May 2017
    My wife booked this property for a couple of days for my birthday celebration. Howard is extremely accommodating the house came with everything! His employee Keith did...
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    About this property
    220+ Acres W\ Tennis Cts, Indoor / Outdoor Pool, Canoe, Fishing Boat, Hot Tub. New first time rental of 4 BR, 2BA, Cape Cod style, sleeps 10-12. New fully equipped kitchen w/ center island, indoor and outdoor barbecues, wine cooler, 2 fireplaces, large deck with 8 person hot tub and super seating...
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    Lenox, Berkshires 01240
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Stephentown, NY
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Mountain Views
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Outdoor Dining Area
    • Washer
    • Grill
    • DVD Player
    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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    Stephentown, New York 12168
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Lee
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Suitability
    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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    Location Information
    Lee, Berkshires 01238
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 6
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