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Monterey Holiday Rentals

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    All 29 Rentals in Monterey
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    Monterey
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Monterey
    5 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Monterey
    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Monterey
    Studio, 2 Bathrooms, Sleeps 7 Quick View
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    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
    Monterey
    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • 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
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • 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
    Monterey
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • 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
    Berkshire lake house on lake Garfield, Monterey MA; private, 4 BR, sleeps 101 / 29
    (8)Excellent
    Monterey
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Internet Access
    • Washer
    • DVD Player
    • Housekeeping Included
    • Central Heating
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Monterey, Berkshires 01245
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Historic Home by Butternut Ski Mountain, Great Barrington and Appalachian Trails1 / 24
    (1)Excellent
    Monterey
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Internet Access
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    Pet friendly
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    Smoking allowed
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    Monterey, Berkshires 01230
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Monterey
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Internet Access
    • Parking
    • Patio
    • Washer
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Monterey, Berkshires 01230
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Berkshires Splendor - Year Round Relaxation And Activities For The Whole Family!1 / 17
    (7)Excellent
    Monterey
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Washer
    • Central Heating
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Monterey, Berkshires 01245
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Beautiful Contemporary on Four Acres in the Berkshires (Monterey) with WIFI1 / 21
    (13)Excellent
    Monterey
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
    • DVD Player
    • Central Heating
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    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Monterey, Berkshires 01245
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Monterey
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Monterey, Berkshires 01245
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    Charming Family Lake House1 / 10
    (3)Very good
    Monterey
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    • Patio
    • DVD Player
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Monterey, Berkshires 01245
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Monterey
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Skiing: Property Is In A Ski Resort
    • Patio
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Monterey, Berkshires 01245
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    Beautiful Waterfront House Rental- Right on Lake Garfield1 / 22
    (17)Very good
    Monterey
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • DVD Player
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Monterey, Berkshires 01245
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Monterey
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Monterey, Berkshires 01245
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Dock on Lake Garfield, WiFi,  FAMILY FUN!1 / 16
    (15)Very good
    Monterey
    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Patio
    • DVD Player
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Monterey, Berkshires 01245
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
    Monterey
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Patio
    • Terrace
    • Internet Access
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Monterey, Berkshires 01245
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    The following rentals are within 10 kilometres of Monterey.
    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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    • Central Heating
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Waterfront
    • Patio
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 2018
    We had an excellent time with our two kids (7 and 8). The house is right on the lake with a great deck and amazing views. We used the kayaks every day. Location was great...
    Reviewed 22 June 2018
    Perfect location, perfect weather, beautiful view! Excellent owner, Carol, who responded to all our questions immediately. Would go back again in a minute.
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    About this property
    Let this serene lakefront Great Barrington area cottage in New Marlborough serve as your ultimate home-away-from-home! Featuring 2 bedrooms, 1-bathroom, and enough room to sleep 4 guests, this year-round vacation rental cottage is sure to give you an experience in the Berkshires that you will never...
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    New Marlborough, Berkshires 01230
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Romantic Berkshire Cottage on Storybook Estate1 / 10
    (1)Excellent
    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Terrace
    • Cable/satellite TV
    • Outdoor Dining Area
    • Internet Access
    • DVD Player
    • Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2017
    What a wonderful, magical place, heaven on earth! From the moment we were greeted warmly by Denise and entered our Tiny House, we knew this was such a special place.The sound of...
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    About this property
    Charming, One Bedroom Cottage, former sculpting studio on the Santarella Estate in Tyringham, MA. Known as the 'Silo Studio', there is a bedroom with queen bed upstairs, sitting room, wet bar with Micro/Fridge and bath downstairs. Fall asleep to sounds of babbling brook and views to pond and forest...
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    Tyringham, Berkshires 01264
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Santarella Estate and Gardens in Tyringham, MA is a magical destination in the heart of one of the Berkshires' most beautiful valleys, located 3 miles from Interstate 90 and 15 minutes from most of the principal attractions (Tanglewood, Jacob's Pillow, Norman Rockwell museum, etc.) Pictures are...
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    Tyringham, Berkshires 01264
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    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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    New Marlborough, Berkshires 01230
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Charming and Spacious Colonial Farmhouse on 4 Acre Estate1 / 15
    (1)Average
    Tyringham
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Washer
    • Mountain Views
    • Central Heating
    • Balcony
    • Wi-Fi
    • DVD Player
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 July 2017
    The grounds are beautiful with lovely gardens. Denise is very friendly and accommodating (like when my son-in-law landed his drone in a tree). The kitchen is well equipped. We...
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    About this property
    Located on the Santarella Estate, an historic site located in the the Massachussetts' Berkshires. The colonial home is the former residence of sculptor Sir Henry Hudson Kitson. The estate includes the landmark, iconic storybook style 'Gingerbread House,' designed by Kitson to look like an English...
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    Tyringham, Berkshires 01264
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Tyringham
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
    About this property
    The Tentrr Running Spring Farm campsite. A hidden camp surrounded by the Berkshire mountains. Adjacent to the Appalachian Trail and the Tyringham Cobble for long or short hikes. Swimming and boating are close by on Goose Pond, Lake Garfield and Beartown State Forest. Kids 13 and under might enjoy...
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    Tyringham, Berkshires 01255
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    New Marlborough
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
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    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
    New Marlborough
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Smoking allowed
    About this property
    Bring your loved one along on a Berkshires getaway in this 1-bedroom, 1-bathroom vacation rental in New Marlborough. Nestled under the pine trees on the edge of Lake Buel, you'll have right-of-way access to the lake and unbeatable views of the picturesque landscape. Launch the 2 provided kayaks in...
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    New Marlborough, Berkshires 01230
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    New Marlborough
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Private Garden
    • Central Heating
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    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
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    • Skiing: Property Is In A Ski Resort
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    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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    Location Information
    New Marlborough, Berkshires 01244
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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