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Homes and Estates in Lakeville, CT and nearby

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    All 30 Rentals in the Lakeville Area
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    $250
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    1 / 19
    5 of 5 stars (3) Excellent
    Lakeville
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    The following rentals are within 15 miles of Lakeville, Connecticut.

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    1 / 30
    Ancram, NY
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    $175
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    1 / 11
    Hillsdale, NY
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    $375
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    1 / 13
    West Cornwall
    3 Bedrooms / 3 Bathrooms / Sleeps 10
    travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    West Cornwall, Connecticut 06796
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    $200
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    1 / 14
    5 of 5 stars (1) Excellent
    Copake, NY
    3 Bedrooms / 1 Bathroom / Sleeps 6
    travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    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... View all property information
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    Location Information
    Copake, New York 12516
    5 of 5 stars Reviewed February 6, 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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    $725
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    1 / 35
    Hillsdale, NY
    5 Bedrooms / 5 Bathrooms / Sleeps 14
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    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
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    Location Information
    Hillsdale, New York 12529
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    1 / 25
    5 of 5 stars (2) Excellent
    Hillsdale, NY
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Hillsdale, New York 12529
    5 of 5 stars Reviewed May 20, 2015
    Just returned from a week end stay with friends in this property. OH LA LA !!!!!! It was HEAVEN ON EARTH. I wanted to say THANKS to Eileen and William for this wonderful and...
    5 of 5 stars Reviewed October 26, 2014
    Many thanks to Bill and Eileen. We had a wonderful week and returned to the UK feeling relaxed and contented. A lovely lodge with all comforts included. Would happily stay...
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    $425
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    1 / 18
    5 of 5 stars (1) Excellent
    Hillsdale, NY
    3 Bedrooms / 2 Bathrooms / Sleeps 13
    traveler have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Hillsdale, New York 12529
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    1 / 15
    5 of 5 stars (3) Excellent
    Sharon
    3 Bedrooms / 1 Bathroom / Sleeps 5
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    Amenities & Details
    • Air Conditioning
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    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
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    Location Information
    Sharon, Connecticut 06069
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    $750
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    1 / 20
    Cornwall Bridge
    3 Bedrooms / 3 Bathrooms / Sleeps 7
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    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
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    Location Information
    Cornwall Bridge, Connecticut 06754
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    1 / 11
    Copake Falls, NY
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Safe
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
    • x
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    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
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    Location Information
    Copake Falls, New York 12517
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    $180
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    1 / 7
    4.5 of 5 stars (6) Very good
    Millerton, NY
    4 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Dishwasher
    • Grill
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Upstate NY, Southern Berkshires, this charming 1800's cottage is the perfect getaway for friends and family at a reasonable price. House sits on 1-1/2 acres of plush lawn and is situated near the NY, Mass. and Connecticut borders. The area is chock full of spectacular views of dairy farms, green... View all property information
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    Location Information
    Millerton, New York 12546
    4 of 5 stars Reviewed July 22, 2014
    Beautiful grounds; Quaint, older house (not an even floor in the whole house), fully stocked with amenities; perfect location for exploring Taconic State Park. We had fun using...
    4 of 5 stars Reviewed August 6, 2013
    It's not the Hilton, but then, you weren't looking for that were you? Walking in is like stepping back in time. This is a lovely old farm house home, decorated appropriately and...
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    $500
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    1 / 8
    Pine Plains, NY
    6 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Wheelchair access
    • Elder access
    About this property
    Architect/artist renovated this mid-century house on 17.5 acres. Open-plan, art-filled home is perfect for entertaining. Woods and fields with 2 ponds and trails offer all-season activities, right at home. Near ski slopes, lakes, fishing steams and rivers, the antiques and art galleries of Hudson.... View all property information
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    Location Information
    Pine Plains, New York 12571
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    $150
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    1 / 1
    Goshen
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
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    • Elder access
    • x
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    About this property
    Reserve your get-away for 2014 at the best lake resort community in NW Connecticut, Woodridge Lake ! This property books quickly and far in advance during the summer season and is very popular with families ! We are offering as a seasonal monthly rental this 3 bedroom 2 bath home nestled in the... View all property information
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    Location Information
    Goshen, Connecticut 06756
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    $150
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    1 / 37
    5 of 5 stars (1) Excellent
    Salisbury
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    traveler have booked this property
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    Amenities & Details
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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 17 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
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    Location Information
    Salisbury, Connecticut 06079
    5 of 5 stars Reviewed September 8, 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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    $1,100
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    1 / 17
    4 of 5 stars (1) Very good
    Goshen
    5 Bedrooms / 4 Bathrooms / Sleeps 12
    travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Located in the heart of northwestern Connecticut's elegant Litchfield County. The house is a fully furnished, newly constructed 5 bedroom / 4 bathroom home complete with a beautiful kitchen, fireplace, deck, state-of-the-art home theater system and all the amenities of Woodridge Lake. You will... View all property information
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    Location Information
    Goshen, Connecticut 06756
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    $750
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    1 / 4
    4 of 5 stars (1) Very good
    Copake, NY
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Satellite TV
    • Washer
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    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... View all property information
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    Location Information
    Copake, New York 12529
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    $450
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    1 / 20
    5 of 5 stars (8) Excellent
    Sheffield, MA
    4 Bedrooms / 3 Bathrooms / Sleeps 15
    Overview Reviews (8) Make Inquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The Race Mountain House is set high on the slopes of the Taconic Mountains in Southern Berkshire County. Large, east-facing windows look out over a sweeping view of the Housatonic River Valley. In the early hours, the house floods with warm morning light and sunrises are spectacular. The inviting,... View all property information
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    Location Information
    Sheffield, Berkshires 01257
    5 of 5 stars Reviewed August 6, 2014
    Casey's place was really lovely - just exactly as described! WONDERFUL central great room/dining room for our large group to gather and relax - and beautiful decks for reading...
    5 of 5 stars Reviewed February 23, 2014
    Racebrook Lodge is our "home away from home", and Casey and Dave (the owners) are so incredibly hospitable. This house, their most recent addition to the property, is the GEM of...
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    $100
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    1 / 10
    Hillsdale, NY
    2 Bedrooms / 1 Bathroom / Sleeps 3
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Secluded 1850s eyebrow farmhouse. Open living/dining room with original details. 2 bedrooms. 1 bath. 2 fireplaces. Large sunny stone patio. Gardens, stream, apple trees. Ten acres, surrounded by 1,000-acre Rheinstrom Hill Audubon Bird Sanctuary with miles of trails. Last house on a quiet dead-end... View all property information
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    Location Information
    Hillsdale, New York 12529
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    $200
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    1 / 10
    Copake, NY
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Balcony
    • Dryer
    • Grill
    • Housekeeping...
    • Mountain Views
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Copake, New York 12516
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    $200
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    1 / 11
    5 of 5 stars (14) Excellent
    Falls Village
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (14) Make Inquiry
    Amenities & Details
    • Balcony
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Falls Village, Connecticut 06031
    5 of 5 stars Reviewed April 9, 2015
    I have been traveling to the northwest of Connecticut since my teens, spending a lot of weekends at Lime Rock and Sharon where my daughters spent their summers in a camp. There...
    5 of 5 stars Reviewed February 15, 2015
    Went with the girlfriend for a weekend getaway and chose the perfect place. Extremely relaxing and soothing trip. Everything you need is there, french press? Yep. Towels? Yep...
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    $190
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    1 / 16
    5 of 5 stars (6) Excellent
    Copake, NY
    3 Bedrooms / 2 Bathrooms / Sleeps 9
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    • Air Conditioning
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Fishing...
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Rustic 3 Bedrooms vacation home 1500 sq ft sleeps 9+ There are 7 beds (1 queen bed, 2 single beds (one bed has a trundle bed underneath) 1full futon with single bunk, 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.... View all property information
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    Location Information
    Copake, New York 12516
    5 of 5 stars Reviewed September 5, 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
    5 of 5 stars Reviewed July 24, 2014
    Had family coming from New York, Massachusetts and Connecticut to celebrate my birthday ~ hotels, motels are expensive, and they're not home. This house offered a great place to...
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    1 / 8
    Hillsdale, NY
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Glorious views across meadows to distant mountains. Open-plan living/dining/kitchen with fireplace, and soaring ceiling. Many glass doors lead to decks where you may drink in the view. Great master bedroom suite with state of the art bathroom, two guest rooms, family room, media room and two guest... View all property information
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    Location Information
    Hillsdale, New York 12529
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    $225
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    1 / 16
    5 of 5 stars (4) Excellent
    Copake, NY
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (4) Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    House, 3 Bedrooms + Loft, 2 Baths (Sleeps 7) BE SURE TO CLICK ON THE LINK BELOW TO SEE MORE OF OUR BEAUTIFUL PHOTOS. 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 freshwater lake... View all property information
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    Location Information
    Copake, New York 12516
    5 of 5 stars Reviewed January 6, 2015
    I'm sorry for not responding sooner. Your home was the best vacation rental in which I have stayed today and I rent frequently in the Berkshires. I am going to want to stay there...
    5 of 5 stars Reviewed October 20, 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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    $525
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    1 / 35
    5 of 5 stars (16) Excellent
    Sheffield, MA
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (16) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hours north of New York City, this circa-1770s center chimney colonial will charm and delight your family and guests. 88 acres of land with views of Mt. Washington and Mount Everett... View all property information
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    Location Information
    Sheffield, Berkshires 01257
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    $150
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    1 / 22
    4 of 5 stars (1) Very good
    West Cornwall
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    West Cornwall, Connecticut 06796
    4 of 5 stars Reviewed January 30, 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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    $143
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    1 / 5
    Copake, NY
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Copake, New York 12529
    From
    $225
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    1 / 15
    Bangall, NY
    Studio / 1 Bathroom / Sleeps 2
    Overview Make Inquiry
    Amenities & Details
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Bangall, New York 12581
    From
    $200
    / Night
    View Details
    1 / 9
    Copake, NY
    4 Bedrooms / 3 Bathrooms / Sleeps 17
    Overview Make Inquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    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
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    Location Information
    Copake, New York 12516
    From
    $300
    / Night
    View Details
    1 / 12
    Southfield, MA
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Peaceful setting with a home on 3-acres. Features 270 degree mountain views, a sunny southern exposure, and a front porch and patio to take in all the scenery. Kitchen is over sized with an eating area and a breakfast bar. Master bedroom has ample storage and a private bath with soaking tub.... View all property information
    Make Inquiry
    Location Information
    Southfield, Massachusetts 01259