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New Canaan Vacation Rentals

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    Don't let other travellers get your favourite New Canaan area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 27 Rentals in New Canaan
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    The following rentals are within 25 kilometres of New Canaan.
    Greenwich
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Quaint and immaculate 3 br duplex!1 / 26
    (1)Excellent
    Greenwich
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Weston
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Serene Connecticut Retreat - Luxury 2 bedroom apt1 / 21
    (2)Very good
    Stamford
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Patio
    • Washer
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2015
    The apartment was in a lovely setting, attached to the family house, but totally private. Liz the landlord was very friendly, helpful and knowledgeable of the area. The...
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    About this property
    Completely updated apartment in lovely rural setting but close to everything. Get away without going very far. Take a break from sterile hotel rooms while on business. Private entrance, 2 bedroom, 1.5 bath, fully equipped kitchen, dining room, living room, french doors to patio, balcony off...
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    Stamford, Connecticut 06903
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Greenwich
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Parking
    • Grill
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Lauren Berger Collection is proud to be recognized as one of the best Vacation Rental companies in the world by the best, The Vacation Rental Guide. A forty-five minute drive from Manhattan but a world away from the clamor, this serene, elegant home is set on an acre of rolling lawns in one...
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    Greenwich, Connecticut 06830
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Chappaqua, NY
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Parking
    • Balcony
    • Air Conditioning
    • Internet Access
    • Shared Garden
    • Outdoor Dining Area
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The cottage at Stone Croft is a quick train ride to Manhattan, but looks out on woods and a stream. The cottage is like a two story suite with a full kitchen. There is a queen bed in the main bedroom and a queen sofa bed upstairs. A great place for families and kids. There is a dishwasher,...
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    Chappaqua, Westchester County 10514
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    South Salem, NY
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This wonderful 2500sqf, 3 bedroom 2.5 bathroom home located on 6 acres is decorated with modern and contemporary art creating a homey and comfortable environment which you will enjoy during your stay here. The privacy and quiet is paralleled only by the view of the woods which you can see from the...
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    South Salem, Westchester County 10606
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Private pool house with access to pool and tennis1 / 6
    (1)Excellent
    Darien
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2016
    I stayed lots of place before but David and his family was awesome ! We had a lot of fun in their pool house, tennis and basketball court and mini soccer area.Every single...
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    About this property
    This is a private pool house with queen bed and kitchenette on a 3 acre property. There is a pool steps away as well as a tennis court on the property and you will have full access to both. There is a bathroom with shower and other amenities can be provided. We are close drive to the beach in town....
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    Darien, Connecticut 06820
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Fairfield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
    • Balcony
    • Grill
    • Patio
    • Washer
    • Terrace
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This new contemporary beach house has an open floor plan on the first floor with an 8' granite island that seats 4. Fireplace has a 60' Smart TV that hangs from it. Beautiful dining area seats 10. Outdoor gas grill easily facilitates eating al fresco. Each floor has an outdoor furnished deck. Each...
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    Fairfield, Connecticut 06824
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Greenwich
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Patio
    • Private Garden
    • Secure Parking
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Greenwich, Connecticut 06831
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Weston
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy cottage sits on a family property in a small neighborhood (faces the main house on a circle driveway). It has been renovated with all new appliances and new floors while still maintaining it's cozy retreat feel. Each bedroom features a queen size bed. There is also a screened in porch for...
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    Location Information
    Weston, Connecticut 06883
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Southport
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Grill
    • Ocean Views
    • Air Conditioning
    • Balcony
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand new private one bedroom apartment on estate with full kitchen, marble bathroom and open living room with beautiful views and outdoor shower. Located on the 'Gold Coast' between Westport and Fairfield. A great getaway stocked with beach equipment, bikes and outdoor grill, quality sheets and...
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    Location Information
    Southport, Connecticut 06890
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Stamford
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Central Heating
    • Housekeeping Included
    • Balcony
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In this high-ceiling sunny downtown loft, there is a family atmosphere and eclectic furniture and decor. It is close to local activities (parades, fun-raisers, fun runs...etc), great nightlife, public transport: the bus is across the street, the city center (only a 1/4 mile away), restaurants,...
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    Location Information
    Stamford, Connecticut 06905
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Westport
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Grill
    • Washer
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Its a great house on half an acre. Starting at 199 Per night. All updated. Much better than three pictures.Brand new kitchen appliances. restaurant begin two houses away. Walk to everything. Yes really one minute to stores restaurants markets and lots of stores etc. Shuttle stops at our door to...
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    Westport, Connecticut 06880
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Mount Kisco, NY
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated at the end of a quiet, semi-private road, this delightful Country Retreat offers a tranquil and serene experience for your vacation stay. The lush trees will embrace you and offer a sense of seclusion, yet the wide-open space allows for wandering eyes to breathe in the stunning views of...
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    Location Information
    Mount Kisco, Westchester County 10549
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Easton
    6 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our large and luxurious home is open to you for your enjoyment and relaxation. With 4 en-suite bedrooms and 2 additional bedrooms, the house is able to comfortably accommodate large groups of people for short stays. The house is in immaculate condition and boasts luxury appointments and and...
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    Location Information
    Easton, Connecticut 06612
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 20
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    North Salem, NY
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Balcony
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gracious and well appointed Coach House has been beautifully renovated. The Light and Airy Two Floor cottage is situated on the property of an historic home, and offers a Pool, mature gardens, riding and hiking trails. It's near excellent fishing spots. Dine al fresco on your private patio!...
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    Location Information
    North Salem, Westchester County 10560
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Westport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in 1898, exposed unfinished beams and pillars, Charming low ceilings and a couple of original doors, make it a residence with genuine soul and character. Upstairs is a semi open space, no doors or full walls-half walls separate sleeping spaces. Has a queen bed and a traditional Japanese...
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    Westport, Connecticut 06880
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Bedford, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in a comfortable home in Bedford, NY. You will feel right at home enjoying this house. It sits on 1.5 acres in an upscale neighborhood in one of the most prestigious and elegant New York suburbs. Incredible restaurants, hiking and NYC all within an easy drive. The space Nice big kitchen....
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    Bedford, Westchester County 10506
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Pound Ridge, NY
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A luxury cottage set privately on a 7 acre estate in sylvan Pound Ridge, New York. A perfect setting from which to explore Westchester's horse country, The Hudson Valley, New England's Connecticut villages and New York City. World renowned restaurants are within minutes and recreational activities...
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    Pound Ridge, Westchester County 10576
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Greenwich
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Parking
    • Patio
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Greenwich, Connecticut 06831
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Westport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Patio
    • Ocean Views
    • Air Conditioning
    • Waterfront
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located directly on Long Island Sound in the residential section of Saugatuck Shores, this recently renovated, completely furnished, 3 bedroom, 2 bathroom house offers wide unobstructed views of the water from the front porch and the second floor deck. It has new stainless kitchen appliances, new...
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    Westport, Connecticut 06880
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Westport
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Private Garden
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LOCATION, LOCATION, LOCATION... MY HOME IS CENTRALLY LOCATED, SO EVERYTHING YOU NEED AND WANT IS EASILY ACCESSIBLE. IT'S CLOSE TO THREE BEACHES, DOWNTOWN SHOPPING, RESTAURANTS, HISTORIC WESTPORT COUNTRY PLAYHOUSE, AND RAILROAD STATION! IT'S ALL JUST MINUTES AWAY BY CAR, AND NOT ALL THAT FAR TO...
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    Westport, Connecticut 06880
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Greenwich
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Balcony
    • Air Conditioning
    • Washer
    • Patio
    • Wi-Fi
    • Porch
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming 4 bedroom home at the end of a quiet country lane on a horse farm. Country kitchen with a lovely patio and grill. Heated and cooled with recently installed geothermal enjoy peace and tranquility in a beautiful setting. Horses live on the property, please inquire about lessons or trail...
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    Location Information
    Greenwich, Connecticut 06831
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    Westport
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Terrace
    • Outdoor Dining Area
    • Cable/satellite TV
    • Balcony
    • Washer
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Elegant home was professionally designed to capture the spectacular views of the Ocean. The home was completely remodeled recently and includes a rich interior with state of the art kitchen appliances, wood burning fireplace, washer/dryer, central A/C and internet. Near the end of a quiet...
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    Westport, Connecticut 06880
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Greenwich
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With my children off to college I have an empty 3rd floor (so availability is around the school calendar). Neat 3rd floor unit with its own bedroom, separate sitting room, small fridge, microwave, coffee-maker, bathroom (stall shower), TV, and table for 4. Ideal for someone working weekdays in...
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    Greenwich, Connecticut 06830
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Rye, NY
    5 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My place is good for couples or families with kids. Colonial English Cottage property built in 1925. The house is in a great location close to all the Rye amenities and only 23 minutes to NYC by train. There are a two car garage and plenty of parking in the driveway. You will be 5 walking distance...
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    Location Information
    Rye, Westchester County 10580
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 8
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