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Holiday Homes in Lakeville

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    All 30 Rentals in Lakeville
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    Lake House1 / 13
    (1)Excellent
    Lakeville
    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    4 Bedroom Furnished House in Lakeville Connecticut1 / 42
    (3)Excellent
    Lakeville
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    The following rentals are within 25 kilometres of Lakeville.
    The Cottage at Great Falls1 / 18
    (19)Excellent
    Falls Village
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Renovated Barn1 / 15
    (1)Excellent
    Taconic
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2018
    Bebe (the owner) was extremely communicative from beginning to end. The house was even more beautiful in person. We will definitely be booking here again!
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    About this property
    Charming renovated Barn, very private, with pastoral views. Recently renovated throughout, the house features a double-height, vaulted ceiling in the Kitchen, Dining, and Living Rooms, with great light and views. Open deck off the Living Room overlooking a large, private meadow. Within a...
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    Location Information
    06068, Taconic, Connecticut
    Holiday Rental House - 3 Bedrooms, 3 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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    Amenities & Details
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 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
    06031, Falls Village, Connecticut
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Charming 2+2 Lakeside Cottage on Best Lake in CT1 / 37
    (1)Excellent
    Salisbury
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Wi-Fi
    • Grill
    • Waterfront
    • Mountain Views
    • Outdoor Dining Area
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 September 2014
    My wife and I and two small children stayed at the cabin for one month after a big road trip adventure across the country from California. It was exactly what we needed! Our...
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    About this property
    For the price of a motel room, enjoy a cottage on a lake. Great casual summer-fall vacation place for a small family with room for guests. MINIMUM 14 NIGHT STAY. THOUGH DAILY AND WEEKLY RATES MUST BE SHOWN, WE DO NOT RENT FOR THESE SHORT PERIODS. MONTHLY RATE REQUIRES 32 NIGHT MINIMUM STAY....
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    06079, Salisbury, Connecticut
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Outdoor getaway hunting,fishing,skiing..relaxation1 / 17
    (8)Excellent
    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Porch
    • Balcony
    • Grill
    • DVD Player
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2015
    Comfortable, well equipped house that's ideal for a family or group of friends outing. Roomy with yard, deck and BBQ. Close to Copake, the local lake and the sights of the...
    Reviewed 5 September 2014
    a great location tucked away yet close to all activities. The house is super comfortable and clean. Includes everything you might want, wifi internet is free and easy to access
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    About this property
    Rustic 3 Bedrooms vacation home 1500 sq ft sleeps 9+ There are 6 beds (1 queen bed, 3 single beds (two beds have a trundle bed underneath) and 1 double sofa-bed, a pack & play and high chair for the little one! Full kitchen, 2 baths and large living and dining space. Wrap around deck, BBQ grill,...
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    12516, Copake, New York
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    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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    Amenities & Details
    • 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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    01230, New Marlborough, Berkshires
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Newly Renovated Lakefront Getaway on Robinson Pond1 / 14
    (2)Excellent
    Copake, NY
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Central Heating
    • Wi-Fi
    • Private Garden
    • Grill
    • DVD Player
    • Waterfront
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2018
    I just spent three nights enjoying Ilana’s house on Robinson Pond.Fishing and swimming in the lake.Eating and enjoying cocktails on her beautiful deck.Everything was really nice...
    Reviewed 6 February 2014
    The home fit all 5 of my guests comfortably. It was centrally located to skiing and was a wonderful home and a very cozy experience
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    About this property
    Beautifully restored 2 bedroom (plus attic loft) home brings contemporary living to this hidden gem just 2 hours from NYC. We gutted the house completely incorporating modern amenities like a brand new stainless steel kitchen with granite countertops, hardwood bamboo flooring and a large deck to...
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    Location Information
    12516, Copake, New York
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Apple Cottage1 / 10
    (5)Excellent
    Sheffield, MA
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    • Balcony
    • Parking
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We stayed at the house for thanksgiving weekend — 1 couple each plus child in each suite and our mother in downstairs bedroom. House was ideal mix of informal rustic and luxury...
    Reviewed 25 July 2016
    Our family of four (two adults and a 12 and 8 year old) recently stayed at Apple Cottage with my sister who lives in Boston and had a wonderful week. The house was perfect for...
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    About this property
    Charmingly restored 1840 cottage in the apple orchard of a working organic farm. Completely renovated in 2015 with thoughtful amenities, fresh eggs and produce and acres of trails and views. Close to waterfalls and lakes. Nearby ski hills, Tanglewood concerts, theatre, film festival, dance and...
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    Location Information
    01257, Sheffield, Berkshires
    Holiday Rental House - 3 Bedrooms, 6 Bathrooms, Sleeps 8
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    Stanfordville, NY
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Waterfront
    • Patio
    • Terrace
    • Grill
    • Central Heating
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our very secluded and romantic log cabin sits on 85 acres of woodland with its own 3.5 acre lake, streams, forest, and even a 40' gorge. Nearest neighbor is 1/4 mile away through the woods and we won't bother you! Enjoy the interior wood burning fireplace and covered front porch overlooking your...
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    Location Information
    12581, Stanfordville, New York
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cornwall Bridge
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Mountain Views
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Internet Access
    • Private Indoor Pool
    • Air Conditioning
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Prana Residence-Spa creates an environment for relaxation and the rejuvenation of vital life (prana). If you appreciate tranquility in the pursuit of personal happiness and are inspired by unique surroundings, personal spa facilities and select services, Prana Residence-Spa is waiting for you....
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    Location Information
    06754, Cornwall Bridge, Connecticut
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Copake Falls, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Mountain Views
    • Washer
    • Central Heating
    • Porch
    • Outdoor Dining Area
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ski the Berkshires at Catamount 10 minutes away and Butternut 30 minutes away. Beautifully renovated cottage in walking distance to Taconic State Park. Enjoy farm to table dining nearby. Hike to Birkshires' Bash Bish Falls, bike on the Harlem Valley Bike Trail, and swim in the spring fed iron ore...
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    Location Information
    12517, Copake Falls, New York
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Ancram, NY
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Mountain Views
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perched on over 150 acres, this upscale and distinctive country villa boasts graceful, pastoral views from all directions, offers gracious accommodations and an exquisite getaway destination for family gatherings, celebrations or corporate retreats. Drive up the expansive driveway and past the...
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    12502, Ancram, New York
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Sheffield, MA
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    01257, Sheffield, Berkshires
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Stanfordville, NY
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Shared Garden
    • Parking
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Updated apartment with panoramic views off private deck with one bedroom, full bathroom, equipped kitchen, dining area and living room, and onsite guest parking. Nestled in Northern Dutchess County, we are a great base location from nearby New York towns such as Red Hook, Rhinebeck and Millbrook,...
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    12581, Stanfordville, New York
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Millerton, NY
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Central Heating
    • Balcony
    • Terrace
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1700’s Farmhouse, on a lovely horse farm is like staying in an antique with all the modern conveniences. Chickens mill about and retired horses dot the landscape. Relax in front of the gas fireplace in the winter, and in the summer sit on the deck listening to the babbling brook . Bike the...
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    12546, Millerton, New York
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Sharon
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our stately home is surrounded by gardens, fields and woods, with a stream meandering through it. There is a terrace for outdoor dining, a fire pit for campfires and plenty of lawn for playing ball games and croquet.
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    Location Information
    06069, Sharon, Connecticut
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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    Comfortable Rustic Cottage on 4 Wooded Acres with Brook1 / 22
    (3)Very good
    West Cornwall
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Porch
    • Parking
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2015
    Really enjoyed staying here with y sister and partner and my family (three young kids), who played endlessly in the stream which was full of frogs and stones. We could relax...
    Reviewed 30 January 2015
    This was a wonderful cabin, no bells or whistles, but all of the amenities. It was comfortable clean and very spacious. The floor plan lends itself to lots of nooks and crannies...
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    About this property
    Furnished cottage, with large deck, on 4 acres of woods, with brook and 200 feet Housatonic River frontage. Use of Sharon beach, tennis courts, and children's play area. The brook will dry up during summer dry spells. Located in the beautiful Litchfield Hills, the cottage is 2 minutes from...
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    Location Information
    06796, West Cornwall, Connecticut
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Terrace
    • Washer
    • Balcony
    • Central Heating
    • Patio
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A single storey house with a large basement less than 100 yards from the boat launch to the lake. Swimming, fishing, boating, walking, climbing, cycling and skiing all within 20 minutes ride from the house. A perfect location for all of these activities, plus a quiet location if you just want to...
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    12516, Copake, New York
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    01230, New Marlborough, Berkshires
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    West Cornwall
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    • Internet Access
    • Porch
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Architect-designed, contemporary, 3-bedroom country home. Sited on five private hillside acres with breathtaking views of the Housatonic River Valley in the foothills of the Berkshire Mountains. With geothermal heating and air conditioning, heated floors, wood, slate, and stone flooring, gourmet...
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    06796, West Cornwall, Connecticut
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Cozy  Copake Lake Cottage1 / 4
    (1)Very good
    Copake, NY
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Waterfront
    • Porch
    • DVD Player
    • Washer
    • Grill
    • Central Heating
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cottage with a view of Copake Lake has 3 bedrooms and a loft. The master bedroom contains a queen bed, a second bedroom contains a double bed, and the third bedroom contains two bunk beds. The recently-renovated bathroom has a washer/dryer and a whirlpool tub. There is also a sunroom and the...
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    12529, Copake, New York
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    The perfect Southern Berkshire winter vacation esc1 / 14
    (1)Excellent
    Sheffield, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 October 2015
    Beautifully decorated house nestled in the Berkshires. A true getaway. Plenty of room for a family with the latest TV/computer set up. Big kitchen with the best appliances...
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    About this property
    This beautiful and secluded winter utopia is perfect for your Berkshire winter vacation getaway. Private and secluded, this home is nestled on five private acres in the woods located conveniently within fifteen minutes to many area attractions. Wether you are looking to ski the slopes, capture the...
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    Location Information
    01257, Sheffield, Berkshires
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    Location Information
    01230, New Marlborough, Berkshires
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Salisbury
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    East Twin Lakes, a charming three-bedroom lakefront cottage with private two docks, 200 feet of shore front with gorgeous views. The lake is clean and has the best fishing in Connecticut. Enjoy boating, water skiing, canoeing, sailing or fishing. The cottage is furnished and has a window air...
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    Location Information
    06068, Salisbury, Connecticut
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Amenia, NY
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Magnolia Cottage!! 44,000 Gallon in-ground saltwater pool. Covered Front Porch with wicker chairs. Gardens, Greenhouse, & Walking Trails. Side Patio with BBQ and Gas Fire Pit. Basic Stocked Fridge (milk, eggs, butter, jams, etc.). High thread-count cotton linens and towels. Two...
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    Location Information
    12501, Amenia, New York
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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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
    01230, New Marlborough, Berkshires
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
    06058, Norfolk, Connecticut
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 5
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    New Marlborough, MA
    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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    Location Information
    01230, New Marlborough, Berkshires
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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