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Colebrook Vacation Rentals

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    Don't let other travelers get your favorite Colebrook area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 24 Rentals in Colebrook
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    Colebrook
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    The following rentals are within 15 miles of Colebrook.
    Waterfront Cottage - 10 Mins to Great Barrington!1 / 24
    (4)Excellent
    New Marlborough, MA
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Quiet first floor apartment in Torrington1 / 12
    (6)Excellent
    Torrington
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Monterey, MA
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Air Conditioning
    • DVD Player
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The lakeside house is built on a 1.1 acre lot with view of Lake Garfield. It is only three minute walk to the public beach with life guards on site. In the summer, Jacob’s Pillow Dance Center and Tanglewood Music Center are about 25 to 30 minutes away. In the winter, Ski Butternut resort is about...
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    Location Information
    Monterey, Berkshires 01245
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    The Cottage at Great Falls1 / 18
    (20)Excellent
    Falls Village
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Washer
    • DVD Player
    • Mountain Views
    • Waterfront
    • Central Heating
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We just booked a weekend in March 2019 for our 10th anniversary. This will be our third stay. Our previous visits had been during the summer months, so we're looking forward...
    Reviewed November 15, 2017
    Danielle responded to my vacation request in record time, and was very attentive before, during and after our stay. Everything was perfect when we arrived - the cottage was...
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    About this property
    Rare property available for vacation rental in Falls Village Ct Originally dating to 1800 's this highly unique property was purchased in 1999 by artist and master craftsman Mario Genova. The interior features plaster throughout, stone, marble and terra cotta mosaic flooring and wonderful...
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    Location Information
    Falls Village, Connecticut 06031
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Enjoy horses and the largest recreational lake in Massachusetts1 / 20
    (1)Excellent
    East Otis, MA
    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 November 7, 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
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    Windy Top Stone Cottage1 / 26
    (1)Excellent
    North Granby
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Secure Parking
    • Patio
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    • Grill
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 7, 2018
    My wife and I arrived at Windy Top in the middle of a snowstorm. What a perfect place to be snowed in! The cottage was beautifully decorated for the season and our hosts, Ken...
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    About this property
    The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to “summer” in the early part of the 20th Century. The cottage was the place where the domestic staff stayed when...
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    Location Information
    North Granby, Connecticut 06060
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Winsted
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Private Yard
    • Parking
    • Waterfront
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lake house rebuilt in 2016 to high standards. Lake front, swimming, fishing, kayaking. Central air. Choice location on beautiful lake with full boating. Dockage for your boat directly in front of the cottage. Nice, direct waterfront with lawn, deck and good swimming area. Gas fireplace and very...
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    Winsted, Connecticut 06098
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    North Granby
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Yard
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Loft at Lost Acres is a wonderfully private, rural getaway! This bright and comfortable space is located on the upper floor of the Lost Acres Vineyard service barn. Originally intended for the caretaker, the owners have decided to offer it to the public to enjoy the beauty of the vines & the...
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    Location Information
    North Granby, Connecticut 06060
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Monterey, MA
    5 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Location Information
    Monterey, Berkshires 01245
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 6
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    Riverwood - Cozy Carriage House in the Woods1 / 11
    (1)Excellent
    Falls Village
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Wi-Fi
    • Air Conditioning
    • Private Yard
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 27, 2018
    I would rate this higher than 5 stars. The location was perfect for our week. Close to family in the area, hiking, kayaking and motorcycling. The carriage house is immaculate...
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    About this property
    Lovely second-story guest house on wooded property. Generously sized bedroom with queen bed, comfortable bathroom with therapeutic river stone walk-in shower, petit fully equipped kitchen, and relaxing main room with leather dual-reclining loveseat, flat screen TV, private deck and dining area....
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    Location Information
    Falls Village, Connecticut 06031
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Otis, MA
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Grill
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    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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    Location Information
    Otis, Berkshires 01255
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    New Marlborough, MA
    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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    New Marlborough, MA
    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
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    Monterey, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    • Washer
    • Patio
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Smiling Dog Meadow' offers the ideal escape to Massachusetts's scenic Berkshires region! Nestled on 5 acres, this newly renovated home for up to 12 guests features 4 bedrooms, 2.5 baths, and a waterfront location with access to a private dock and several boats. Create unforgettable memories at...
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    Monterey, Berkshires 01245
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Monterey, MA
    Studio, 2 Bathrooms, Sleeps 7 Quick View
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    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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    Location Information
    Monterey, Berkshires 01245
    Rental Home - 2 Bathrooms, Sleeps 7
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    Harwinton
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Weekly rental April through December, monthly rental offered January thu March. 2 bedroom, 1 bath, fireplace, with beautiful views of the lake Enjoy a classic New England vacation in this direct lake front home on Harwinton Lake. Relax and enjoy the pretty scenery and breezes in this quiet lake...
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    Location Information
    Harwinton, Connecticut 06791
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    New Marlborough, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Private Yard
    • 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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    Location Information
    New Marlborough, Berkshires 01230
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    West Hartland
    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 - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    New Marlborough, MA
    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 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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    Location Information
    New Marlborough, Berkshires 01230
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Monterey, MA
    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 gorgeous 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 for 10! Enjoy sitting out on the deck to take in the water views, gathering around the fire pit to roast s’mores, or...
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    Monterey, Berkshires 01230
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Otis, MA
    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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    Location Information
    Otis, Berkshires 01029
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Monterey, MA
    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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    Location Information
    Monterey, Berkshires 01245
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Norfolk
    4 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Skiing: Property Is In A Ski Resort
    • Central Heating
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the bucolic getaway you've been craving with a stay at this 4-bed, 1.5-bath Norfolk house! Truly off-the-grid, this vacation rental is void of all modern distractions, but complete with a fully equipped kitchen, charcoal grill, furnished patio and 2 gas stoves - creating a peaceful...
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    Location Information
    Norfolk, Connecticut 06058
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 5
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    Colebrook Flight and Weather Info
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    Bradley Intl Airport
    21.4 miles from Colebrook
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