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Holiday Rentals and Homes in Lakeville, CT

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    1 / 42
    5 of 5 stars (3) Excellent
    Lakeville
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 23
    Lakeville
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    The following rentals are within 25 kilometers of Lakeville, Connecticut.

    1 / 14
    5 of 5 stars (1) Excellent
    Copake, NY
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 26
    5 of 5 stars (2) Excellent
    Copake, NY
    3 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Grill
    • Parking
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Mountain Views
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Elegant and tranquil 2 level lakefront retreat, the perfect escape for any season. 3 bedrooms, 2 bath plus a powder room, gourmet kitchen with island counter, cathedral ceilings, large deck facing lake and spectacular Taconic mountain range + small screened porch. Breathtaking lake and mountain... View all property information
    Location Information
    Copake, New York
    5 of 5 stars Reviewed 30 May 2016
    Fantastic place to unwind and reconnect with nature: huge oak trees frame the view of the lake & mountains in the distance. Birds, wind, and occasional fish splashing in the...
    5 of 5 stars Reviewed 31 October 2015
    We were delighted to find this attractive cottage on Robinson Pond. We enjoyed watching the ducks and geese out the expansive windows and were so pleased to see no other humans...
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    1 / 11
    Copake Falls, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Mountain Views
    • Washer
    • Central Heating
    • Porch
    • Outdoor Dining Area
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Copake Falls, New York
    1 / 21
    Cornwall Bridge
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Mountain Views
    • DVD Player
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Private Indoor Pool
    • Air Conditioning
    • Sauna
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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.... View all property information
    Location Information
    Cornwall Bridge, Connecticut
    1 / 10
    5 of 5 stars (4) Excellent
    Sheffield, MA
    3 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    • Balcony
    • Parking
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Sheffield, Berkshires
    5 of 5 stars 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 our...
    5 of 5 stars Reviewed 16 May 2016
    Tucked away down a country road, farm fresh eggs for breakfast, wonderful rustic cottage details everywhere, Apple Cottage does not disappoint! The cottage easily accommodated 7...
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    1 / 11
    5 of 5 stars (1) Excellent
    Falls Village
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Garden
    • Parking
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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.... View all property information
    Location Information
    Falls Village, Connecticut
    5 of 5 stars Reviewed 1 week ago
    I only wish my mobility was better to take a walk on this beautiful property very close to Lime Rock Park and many other cultural attractions. Owners were very nice and obviously...
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    1 / 15
    5 of 5 stars (3) Excellent
    Sharon
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Washer
    • Outdoor Dining Area
    • Internet Access
    • Grill
    • DVD Player
    • Air Conditioning
    • Mountain Views
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Want to get away from it all? Just 2 hours away from New York City or Take Metro North and hop in a cab. This house is the perfect getaway located in Sharon, Litchfield County, Connecticut which is in the foothills of the Berkshires. Sharon is the quintessential New England small town. Quiet and... View all property information
    Location Information
    Sharon, Connecticut
    1 / 26
    5 of 5 stars (8) Excellent
    Hillsdale, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Parking
    • Mountain Views
    • Central Heating
    • Washer
    • Grill
    • Satellite TV
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    3 bedrooms, 2 full baths, living room, dining room, kitchen, loft area. Private and secluded log cabin chalet is situated on three picturesque acres overlooking tall pines and forests with heartwarming winter mountain views. The chalet was built in 2003 and has gorgeous stone countertops and two... View all property information
    Location Information
    Hillsdale, New York
    5 of 5 stars Reviewed 2 July 2016
    Had a short trip with the family to attend a wedding in the berkshires. The house is beautifully decorated and perfectly equipped. It has surpassed our expectations and we just...
    5 of 5 stars Reviewed 21 December 2015
    Owners were delightful to deal with. House was clean and well equipped. Would definitely rent again for a ski weekend! Really enjoyed family dinner at "The Gypsy Joint" in nearby...
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    1 / 11
    5 of 5 stars (2) Excellent
    Hillsdale, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Washer
    • Parking
    • Wi-Fi
    • DVD Player
    • Mountain Views
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    We found a great circa 1845 house in the Berkshire/Taconic Mtn area and fully renovated the entire building creating retail shops and a sophisticated but casually comfortable 2 BR apt. saving many of the original building features. Fully equipped efficiency kitchen with a W/D, marble bath, sleeps 6... View all property information
    Location Information
    Hillsdale, New York
    5 of 5 stars Reviewed 4 November 2015
    C'était tellement bien, que j'ai déjà envie d'y retourner!! As a French citizen, I can affirm that my stay at Lynne and Bill's loft was perfect! No noise, comfortable and with...
    5 of 5 stars Reviewed 27 September 2015
    Bill and Lynne, the proprietors were wonderful. Very accommodating and helpful. Although located on highway 23, there is very little road noise as the apartment is brand new...
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    1 / 15
    Copake, NY
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Satellite TV
    • Grill
    • Washer
    • Internet Access
    • DVD Player
    • Parking
    • Skiing: Property Is...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Please note that rates listed and minimum days to rent are for standard nights. Please contact owner for rates during prime dates (e.g., summer when pool is open and holidays). This house had extensive renovations in 2014 and has free wifi throughout. The kitchen and living room were combined for... View all property information
    Location Information
    Copake, New York
    1 / 37
    5 of 5 stars (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
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    For the price of a motel room, enjoy a cabin on a lake. Great casual summer-fall vacation place for a small family with room for guests. MINIMUM 14 DAY STAY. THOUGH DAILY AND WEEKLY RATES MUST BE SHOWN, WE DO NOT RENT FOR THESE SHORT PERIODS. SEE NOTE BELOW. Great room, master bedroom, and... View all property information
    Location Information
    Salisbury, Connecticut
    5 of 5 stars 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 pace...
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    1 / 14
    5 of 5 stars (1) Excellent
    Sheffield, MA
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Patio
    • Washer
    • Wi-Fi
    • Satellite TV
    • Private Outdoor...
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Sheffield, Berkshires
    5 of 5 stars 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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    1 / 10
    South Egremont, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Private Garden
    • Parking
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    complete home 3 bedrooms,2 baths,living,dining,kitchen,and large deck(with a great view).Great location,at the foot of Mt.Washington state forest,next door to Jug End preserve,near Bash Bish falls.2 miles to Catamount ski area,5 to Gt.Barrington MA,5 to Hillsdale NY,10 to Twin Lakes,and salisbury... View all property information
    Location Information
    South Egremont, Berkshires
    1 / 11
    5 of 5 stars (18) Excellent
    Falls Village
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
    • Balcony
    • Grill
    • Satellite TV
    • Mountain Views
    • Central Heating
    • Hot Tub
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Falls Village, Connecticut
    4 of 5 stars Reviewed 2 weeks ago
    Enjoyed our stay at this beautiful, well appointed cottage and would book again. Only issue is the lack of air conditioning which can be a problem if weather is hot and humid.
    5 of 5 stars Reviewed 3 weeks ago
    We spent a very relaxing weekend here and took great advantage of the deck overlooking the river. Everything was as described and depicted in photos. It was awesome to hear the...
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    1 / 13
    West Cornwall
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Washer
    • Air Conditioning
    • Satellite TV
    • Mountain Views
    • Internet Access
    • Porch
    • DVD Player
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    West Cornwall, Connecticut
    1 / 15
    5 of 5 stars (8) Excellent
    Copake, NY
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Air Conditioning
    • Wi-Fi
    • Porch
    • Grill
    • Washer
    • Satellite TV
    • Parking
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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,... View all property information
    Location Information
    Copake, New York
    4 of 5 stars 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 area...
    5 of 5 stars 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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    1 / 18
    5 of 5 stars (1) Excellent
    Hillsdale, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 13 | Quick View
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    • Washer
    • Satellite TV
    • DVD Player
    • Porch
    • Parking
    • Internet Access
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Cozy modern log cabin nestled in the Berkshires in a large wooded area with landscaped yard on a small river. The cabin has a full service kitchen and a great room with dining and lounging space. There is a full entertainment center with furnished recorded music and movies. Bedrooms and bath are... View all property information
    Location Information
    Hillsdale, New York
    1 / 35
    Hillsdale, NY
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
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    • x
    About this property
    This extremely private luxury home is situated on 48-acres at the end of a cul de sac and is located two miles from NY Route 22 in Columbia County just 10 minutes from the Massachusetts boarder and 30 minutes from the Vermont border. Recently renovated, this contemporary home with 5 bedrooms... View all property information
    Location Information
    Hillsdale, New York
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    1 / 16
    5 of 5 stars (4) Excellent
    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    About this property
    House, 3 Bedrooms + Loft, 2 Baths (Sleeps 7)<BR><BR>BE SURE TO CLICK ON THE LINK BELOW TO SEE MORE OF OUR BEAUTIFUL PHOTOS.<BR><BR>This three bedroom , two living rooms with flate screen home theater system, 2 Baths, plus sleeping loft(or office) has it all. Our deeded lake access on a clean... View all property information
    Location Information
    Copake, New York
    5 of 5 stars Reviewed 20 October 2014
    We spent seven days at this house in the New York side of the Berkshires. I'd never rented in this way before so I was a little nervous. When we got there, we were really wowed...
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    1 / 30
    Ancram, NY
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Waterfront
    • Air Conditioning
    • Internet Access
    • Private Outdoor...
    • Mountain Views
    • Satellite TV
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Ancram, New York
    1 / 10
    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
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Copake, New York
    1 / 10
    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
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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.... View all property information
    Location Information
    New Marlborough, Berkshires
    1 / 9
    Copake, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 17 | Quick View
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    • Internet Access
    • Balcony
    • Grill
    • DVD Player
    • Central Heating
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Completely furnished kitchen, bedrooms and bathrooms. Master bedroom has full bath, large window overlooking lake, secondary bedroom has 1/2 bath. Downstairs area, has two curtained rooms with king beds, two bunk beds and a 1/2 bath. Dock on property gives access to lake within 30 feet of house,... View all property information
    Location Information
    Copake, New York
    1 / 15
    5 of 5 stars (1) Excellent
    Bangall, NY
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Amenities & Details
    • Satellite TV
    • Patio
    • Waterfront
    • DVD Player
    • Grill
    • Porch
    • Central Heating
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    ROMANTIC log cabin with lovely stone fireplace designed for only 2 sits on the shore of its own 3.5 acre lake on 85 acres of land. Your closest neighbor will be 1/4 mile away! Enjoy the wildlife - heron, wild turkeys, deer, geese, turtles, many varieties of birds, etc. Explore 85 acres of... View all property information
    Location Information
    Bangall, New York
    5 of 5 stars Reviewed 9 November 2015
    My husband and I celebrated our 10th wedding anniversary at Hudson Valley Cabin. It is THE MOST romantic, secluded, peaceful place we could have asked for. The cabin is very...
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    1 / 6
    Copake, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Well appointed comfortable 4 season home short walk to lake beach and dock. Large deck with lake views. TV with VCR/DVD Washer/dryer/dishwasher Beds: 1 Queen Bed, 4 Twin Beds View all property information
    Location Information
    Copake, New York
    1 / 22
    4.5 of 5 stars (2) Very good
    West Cornwall
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Porch
    • Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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. Located in the beautiful Litchfield Hills, the cottage is 2 minutes from West Cornwall and its covered bridge,10 minutes from... View all property information
    Location Information
    West Cornwall, Connecticut
    5 of 5 stars 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 from...
    4 of 5 stars 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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