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Vacation Rentals in Lakeville, CT and nearby

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All 31 Rentals in the Lakeville Area
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From
$250
Per Night
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1 / 19
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Lakeville
4 Bedrooms, 3 Bathrooms, Sleeps 8
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The following rentals are within 15 miles of Lakeville, Connecticut.

From
$375
Per Night
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1 / 13
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West Cornwall
3 Bedrooms, 3 Bathrooms, Sleeps 10
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From
$180
Per Night
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1 / 7
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Millerton, NY
4 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$450
Per Night
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1 / 8
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Pine Plains, NY
6 Bedrooms, 4 Bathrooms, Sleeps 12
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Amenities & Details
  • Guest Count
  • # Of Bathrooms
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
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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From
$175
Per Night
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1 / 25
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Hillsdale, NY
3 Bedrooms, 2 Bathrooms, Sleeps 8
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Details Reviews (1) Make Inquiry
Amenities & Details
  • Washer
  • Refrigerator
  • Stove
  • Parking
  • Ceiling Fans
  • DVD Player
  • TV
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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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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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From
$150
Per Night
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1 / 1
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Goshen
3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Dryer
  • Stove
  • Microwave
  • TV
  • Washer
  • Dishwasher
  • Garage
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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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From
$425
Per Night
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1 / 18
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Hillsdale, NY
3 Bedrooms, 2 Bathrooms, Sleeps 13
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Amenities & Details
  • Grill
  • Refrigerator
  • Stove
  • Dishwasher
  • Fireplace
  • DVD Player
  • Washer
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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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From
$200
Per Night
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1 / 15
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Sharon
3 Bedrooms, 1 Bathroom, Sleeps 5
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Amenities & Details
  • Refrigerator
  • Stove
  • TV
  • Grill
  • Washer
  • DVD Player
  • Microwave
  • VCR
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • 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
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From
$200
Per Night
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1 / 14
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Copake, NY
3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
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Amenities & Details
  • Dishwasher
  • Microwave
  • DVD Player
  • Stove
  • Grill
  • Stereo System
  • Refrigerator
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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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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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From
$150
Per Night
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1 / 45
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Hillsdale, NY
4 Bedrooms, 3 Bathrooms, Sleeps 7
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Amenities & Details
  • DVD Player
  • Stereo System
  • TV
  • Dryer
  • Dishwasher
  • Grill
  • Microwave
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
A private enjoyment complete with pond, stream, river and forests yet well within all urban needs. Now accepting 2013-4 Winter Ski Season Rentals, ask. You will be minutes away from world renowned museums, The Clark Institute, MassMoca, The Norman Rockwell Museum, Shaker Museum, Herman... View all property information
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4 of 5 stars Reviewed September 29, 2014
House was wonderful. Pond and woods were fabulous. Very tasteful house with top noth appliances and cookware. We were very comfortable.
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From
$125
Per Night
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1 / 19
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Ancram, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Balcony
  • Refrigerator
  • Internet Access
  • Mountain Views
  • Dishwasher
  • Ceiling Fans
  • Terrace
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Sustainably constructed (LEED and Energy star certified) house on 13 wooded acres. It has 2 bedrooms, each with a double bed. It sits at the top of a hill on a 13 acre wooded site, offering quiet peaceful relaxation and privacy. The living, dining and large kitchen area has a cathedral ceiling... View all property information
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4 of 5 stars Reviewed October 17, 2014
If you are looking for an alternative to chain motels, this is a nice choice. Set amidst 14 acres of pristine woods, the cottage is clean and remarkably spacious. There are two...
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From
$150
Per Night
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1 / 37
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Salisbury
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
Details Reviews (1) Make Inquiry
Amenities & Details
  • TV
  • DVD Player
  • Grill
  • Internet Access
  • Fireplace
  • Stove
  • Refrigerator
  • Deck
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • 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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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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From
$500
Per Night
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1 / 19
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Sheffield, MA
4 Bedrooms, 3 Bathrooms, Sleeps 15
Details Reviews (8) Make Inquiry
Amenities & Details
  • DVD Player
  • Stove
  • Refrigerator
  • Satellite TV
  • Hot Tub
  • Ceiling Fans
  • Fireplace
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
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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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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From
$750
Per Week
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1 / 4
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Copake, NY
3 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (1) Make Inquiry
Amenities & Details
  • Dishwasher
  • DVD Player
  • TV
  • Grill
  • Parking
  • Washer
  • Garage
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
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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From
$300
Per Night
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1 / 10
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Norfolk
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
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Amenities & Details
  • Dishwasher
  • DVD Player
  • Grill
  • Microwave
  • Fireplace
  • Dryer
  • Stove
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This newly renovated 1850's farmhouse in charming, rural Northwest CT has warmth and privacy galore! The home is located on eight acres of land on a dead end road, but is only 4 miles from the center of town! There are three bedrooms, a laundry closet, and 2 full baths upstairs. A jacuzzi... View all property information
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From
$500
Per Night
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1 / 35
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Hillsdale, NY
5 Bedrooms, 5 Bathrooms, Sleeps 14
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Amenities & Details
  • # Of Bathrooms
  • Guest Count
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • 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
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From
$2,000
Per Night
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1 / 30
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Ancram, NY
4 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Washer
  • Patio
  • Stove
  • Refrigerator
  • Microwave
  • Grill
  • Dishwasher
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • 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
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From
$100
Per Night
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1 / 10
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Hillsdale, NY
2 Bedrooms, 1 Bathroom, Sleeps 3
Details Make Inquiry
Amenities & Details
  • Number Of Bedrooms
  • # Of Bathrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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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From
$200
Per Night
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1 / 10
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Copake, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Parking
  • Terrace
  • Dryer
  • Refrigerator
  • Game Room
  • Stove
  • Washer
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • 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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From
$85
Per Night
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1 / 10
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Pine Plains, NY
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
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Amenities & Details
  • # Of Bathrooms
  • Guest Count
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
A large living space with couch and eating area, a bedroom, a shower bathroom and a bare bones kitchen make up the private space/private entrance we have made available in this upstate New York eyebrow colonial. White walls, lots of light, original art, books galore and internet access. What... View all property information
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From
$200
Per Night
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1 / 11
Falls Village
2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Stereo System
  • Microwave
  • Deck
  • Stove
  • Washer
  • TV
  • Dryer
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • 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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5 of 5 stars Reviewed August 20, 2014
My sister and I stayed in the cottage for two nights this summer. It was a totally awesome experience. We were visiting the area where we had spent many wonderful summers years...
5 of 5 stars Reviewed February 10, 2014
I happened upon the cottage more or less by accident, but having stayed there twice since December, I'm confident I'll be returning again and again. The gorgeous (and very...
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From
$100
Per Night
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1 / 8
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Hillsdale, NY
3 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (4) Make Inquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • DVD Player
  • Stove
  • Refrigerator
  • TV
  • Microwave
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Welcome to the quiet confines of Copake Lake nestled in the heart of the Taconic Mountain Range in Columbia County, NY, bordering Massachusetts' Berkshire County. You wake up an hour past dawn, grab a cup of java and sit out on your private deck that overlooks shimmering Copake Lake, a 365 acre... View all property information
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From
$1,250
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1 / 16
Copake, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Number Of Bedrooms
  • Guest Count
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
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... View all property information
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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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From
$150
Per Night
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1 / 8
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Hillsdale, NY
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Refrigerator
  • Fireplace
  • Stove
  • Microwave
  • Internet Access
  • Dishwasher
  • Parking
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • 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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From
$1,100
Per Week
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1 / 17
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Goshen
5 Bedrooms, 4 Bathrooms, Sleeps 12
Booking
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Amenities & Details
  • Microwave
  • Gym
  • Garage
  • Grill
  • Refrigerator
  • DVD Player
  • Dryer
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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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From
$550
Per Night
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1 / 32
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Sheffield, MA
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (16) Make Inquiry
Amenities & Details
  • Hot Tub
  • Parking
  • Fireplace
  • Dishwasher
  • Microwave
  • DVD Player
  • Garage
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • 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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From
$200
Per Night
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1 / 10
Copake, NY
4 Bedrooms, 3 Bathrooms, Sleeps 17
Details Make Inquiry
Amenities & Details
  • Washer
  • Parking
  • Dryer
  • Dishwasher
  • Microwave
  • Satellite TV
  • Stereo System
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • 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
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From
$225
Per Night
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1 / 15
Bangall, NY
Studio, 1 Bathroom, Sleeps 2
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Amenities & Details
  • DVD Player
  • Refrigerator
  • Stereo System
  • Stove
  • Grill
  • Parking
  • Patio
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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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From
$143
Per Night
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1 / 5
Copake, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Microwave
  • Ceiling Fans
  • DVD Player
  • VCR
  • Grill
  • Dryer
  • Stove
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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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From
$125
Per Night
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1 / 22
West Cornwall
2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Refrigerator
  • Satellite TV
  • Washer
  • Deck
  • Porch
  • Parking
  • Dryer
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Winter activities: The cottage is 10 minutes from the Mohawk Mountain Ski Area - 5 trails, 4 lifts and $30 lift tickets; and 45 minutes from Butternut Basin in Great Barrington, MA, and Catamount Ski Area in Hillsdale, NY. Other nearby winter activity includes: walking along Upper River Road... View all property information
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From
$267
Per Night
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1 / 5
South Egremont, MA
4 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • DVD Player
  • Refrigerator
  • Grill
  • Washer
  • Stove
  • Parking
  • Stereo System
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Located directly on the shore of Lake Buel in Great Barrington just minutes away from Tanglewood, Jacobs Pillow and many other attractions. Our family home boasts a 40 foot screened in porch for dining and enjoying the beautiful lake. All rooms are on one floor and you can drive right up to the... View all property information
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