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Holiday Homes in Sandisfield

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    Don't let other travellers get your favourite Sandisfield area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 21 Rentals in Sandisfield
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    Sandisfield
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    The following rentals are within 15 kilometres of Sandisfield.
    Waterfront Cottage - 10 Mins to Great Barrington!1 / 24
    (4)Excellent
    New Marlborough
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Monterey
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Enjoy horses and the largest recreational lake in Massachusetts1 / 20
    (1)Excellent
    East Otis
    1 Bedroom, 1 Bathroom, Sleeps 4 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
    Reviewed 8 November 2018
    I stayed here with a few friends looking to escape the city for a cozy weekend away. Wendy ad Kevin were amazing and went above and beyond their responsibilities as hosts. Wendy...
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    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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    East Otis, Berkshires 01029
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Monterey
    5 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get away from it all at our beautiful Berkshire lakefront wooded retreat. Swim, canoe, kayak, sunbathe, play tennis during the day, then enjoy the evening a short drive away at Tanglewood, Jacobs Pillow, or perhaps go to the movies in Great Barrington. Have dinner at the Red Lion Inn, or one of the...
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    Monterey, Berkshires 01245
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 6
    Otis
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS IS A FULLY FURNISHED LARGE RETREAT IN THE HEART OF THE BERKSHIRES...SKIIING, LAKES, ANTIQUES, CRAFT SHOWS, ARTS, THEATRE ALL NEAR BY.....HOME IS IN A PRIVATE COMMUNITY WITH ITS OWN LAKE, POOLS, STATE OF THE ART FITNESS CENTER, CLUBHOUSE, HIKING TRAILS, TENNIS AND MORE! ONLY 2 1/2 HRS FROM NY...
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    Otis, Berkshires 01255
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
    Colebrook Dream1 / 12
    (1)Excellent
    Colebrook, CT
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Parking
    • Patio
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Washer
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 October 2019
    The house was exactly as advertised. Clean and had everything we needed. I would definitely recommend this rental.
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    About this property
    Welcome to our tastefully decorated home in Colebrook - nestled in the woodlands, this two-acre retreat offers a tranquil escape for up to 6 people and is only a 5-minute drive from town. Curl up by the fire in the family room or grab a blanket and make some smores around the fire pit! Perfect for...
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    Colebrook, Connecticut 06021
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
    West Hartland, CT
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elevate your lakeside retreat at this 3-bedroom, 2-bathroom vacation rental home that has accommodations for 8 in Tolland. Dive into lakeside fun on your private dock and hop on a kayak or stand-up paddleboard for a day of exploring this peaceful lake. When you’re not at the lake, enjoy fabulous...
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    West Hartland, Connecticut 01034
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    New Marlborough
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring your loved one or best friend along on a Berkshires getaway in this 1-bedroom, 1-bath vacation rental in New Marlborough. Nestled just 30 yards from private right-of-way access to Lake Buel, this cabin offers unbeatable views of the lake and the Berkshire Mountains. Launch the 2 new kayaks,...
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    New Marlborough, Berkshires 01230
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    New Marlborough
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Balcony
    • Central Heating
    • Wi-Fi
    • Grill
    • Washer
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Mill River, and our 1905 Queen Anne style Victorian backing onto hundreds of acres of woods, deep in the heart of the Berkshires. Step in and enjoy the peace of sitting on the porch of an old house on a quiet country lane, the wind in the trees and the babble of the nearby stream. The...
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    Location Information
    New Marlborough, Berkshires 01230
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Berkshire Getaway Home with Lake Access1 / 49
    (1)Excellent
    Otis
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Terrace
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 April 2019
    The house is absolutely gorgeous! The grounds are stunning and expansive! And let me tell you about privacy! This home is perched on a hill with all the privacy one could need...
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    About this property
    Our charming, eclectic and nicely decorated 4 bedroom home has an open kitchen and light filled living room area connected to an expansive wrap-around porch, 2 cozy bedrooms upstairs with separate bathroom, 1 additional bedroom and bathroom on main floor and a separate den/TV area downstairs with...
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    Otis, Berkshires 01253
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Monterey
    Studio, 2 Bathrooms, Sleeps 7 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You'll love our hand-hewn post & beam beauty on 13 acres in the Berkshire Mountains of Western Mass located near the Monterey/Great Barrington line, close to everything. Great for summer and winter ski season. Rich in both outdoor and cultural attractions, shopping and antiquing. Located adjacent...
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    Monterey, Berkshires 01245
    Holiday Rental House - 2 Bathrooms, Sleeps 7
    New Marlborough
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Washer
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The guest suite is within 'Keyes House,' a quintessential 19th century Greek Revival colonial. It is conveniently located in a small, bucolic village in Southern Berkshire County that is on the National Register of Historic Districts. The entire home, including the two-room suite, has been...
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    New Marlborough, Berkshires 01230
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Southfield
    1 Bedroom, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Central Heating
    • Parking
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is an exclusive Tentrr site. Tentrr partners with farmers, ranchers, and other property owners to offer unique outdoor accommodations on beautiful private land. Each Tentrr Signature site includes a 10'x12' safari-style canvas tent on a raised platform, and you'll find a queen-size single or...
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    Southfield, Berkshires 01259
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 8
    Monterey
    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Garden
    • Patio
    • Cable/satellite TV
    • Internet Access
    • Secure Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The best vacation home in the Berkshires: 9 private acres (far away from roads and neighbors), 6,800 ft² of living space, 6 bedrooms, sleeps 10 very comfortably. Ideal for 1, 2 or 3 families or those wonderful family reunions. For winter it is 15 minutes from Butternut family ski area (ideal for...
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    Monterey, Berkshires 01245
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
    Monterey
    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Secure Parking
    • Grill
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The best vacation home in the Berkshires: 9 private acres (far away from roads and neighbors), 6,800 ft² of living space, 6 bedrooms, sleeps 10 very comfortably. Ideal for 1, 2 or 3 families or those wonderful family reunions. There is a large heated swimming pool. The pool is completely...
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    Monterey, Berkshires 01245
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
    Otis
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in the woods of East Otis, you’ll have a peaceful stay in the Berkshires at this cozy 2-bedroom, 1-bathroom vacation rental cabin. Comfortably accommodating up to 5 guests, this retreat is perfect for a memorable family vacation. With miles of hiking trails to explore and the Otis Reservoir...
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    Otis, Berkshires 01029
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
    New Marlborough
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Private Garden
    • Central Heating
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in a beautiful, stylish colonial house, built in 1800 and updated for maximum comfort. Open plan kitchen/living room with stunning cathedral ceilings, 5 bedrooms with views onto spacious, private 3-acre property and surrounding farmland. Fully equipped kitchen, washing machine, wood burning...
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    New Marlborough, Berkshires 01230
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    New Marlborough
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Reconnect with Mother Nature at this 2-bedroom, 1-bath cabin loaded with character! Minutes from the Historic Mill River District, this vacation rental provides elements of the home like a well-equipped kitchen, views of the river, and warmth by the wood-burning stove. Listen to sounds of nature on...
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    New Marlborough, Berkshires 01244
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Monterey
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Waterfront
    • Terrace
    • Patio
    • Wi-Fi
    • Grill
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With 150 feet of lakefront property on Lake Buel - a pristine 192-acre mountain lake - this lovely 3-bedroom, 2.5-bath home is sure to be the perfect 3-season getaway. Enjoy sitting on the deck to take in the water views, gathering around the fire pit to roast s’mores, or fishing right off the...
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    Monterey, Berkshires 01230
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Monterey
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Washer
    • Central Heating
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay a 5-minute walk from the Lake Garfield Beach and explore the area's historic attractions, outdoor recreation, and more at this 3-bedroom, 2.5-bath vacation rental! Up to 7 guests can enjoy a classic getaway at this country home, featuring a stone patio, gas grill, screened porch, and all the...
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    Monterey, Berkshires 01245
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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