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New Canaan Holiday Rentals

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    Don't let other travellers get your favourite New Canaan area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 25 Rentals in New Canaan
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    New Canaan
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amazing 1 Bedroom Walking to Magical New Canaan Downtown/ Train/Summer Town Pool1 / 10
    (1)Excellent
    New Canaan
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    The following rentals are within 25 kilometres of New Canaan.
    Mount Kisco, NY
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Quaint and immaculate 3 br duplex!1 / 30
    (3)Very good
    Greenwich
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 October 2018
    Great condo in a convenient location! The condo was immaculate and nicely decorated with a well equipped kitchen and high end appliances. The bedrooms had very comfortable beds...
    Reviewed 18 September 2017
    From opening the front door, we felt at home.It was so inviting, well equipped and we found out with in days that we need a Fridge Freezer with an ice dispenser/cold water in...
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    About this property
    Minutes from Byram beach and also from the main streets of Port Chester, Rye and Greenwich, this fully renovated home boasts hard wood floors, washer dryer, central heating and air conditioning and a wonderful state of the art kitchen with granite counter tops. The property has 3 quaint bedrooms...
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    Greenwich, Connecticut 06830
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Charming and immaculate 3 br duplex!1 / 24
    (8)Excellent
    Greenwich
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Washer
    • Parking
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 October 2019
    Clean and cozy, close to shops and restaurants, would definitely stay again. Owner wad easy to get in contact with and attentive to our needs.
    Reviewed 18 July 2016
    We stayed in Greenwich for a week to attended a family wedding. We needed a rental that was big enough for 3 adults with lots of luggage with reasonable access to NY. This...
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    About this property
    Minutes from Byram beach and also from the main streets of Port Chester, Rye and Greenwich, this fully renovated home boasts hard wood floors, washer dryer, central heating and air conditioning and a wonderful state of the art kitchen with granite counter tops. The property has 3 quaint bedrooms...
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    Greenwich, Connecticut 06830
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
    Weston
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Grill
    • Patio
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    • Internet Access
    • Balcony
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Master Bedroom with four additional bedrooms -- two are double height with lofts. The home features 18' soaring ceilings, an incredible wrap around deck overlooking lawns and gardens. Large Italian eat-in kitchen/family room. Office for 4. Home theater. Whole-house B&O system. Badminton, ping pong,...
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    Weston, Connecticut 06883
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
    Pound Ridge, NY
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    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
    Fairfield
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Housekeeping Included
    • Grill
    • 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, 4 Bathrooms, Sleeps 6
    Memory Lane Farm1 / 11
    (1)Terrible
    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
    Serene Connecticut Retreat - Luxury 2 bedroom apt1 / 21
    (3)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 24 July 2018
    Liz was always available to answer our questions and help with local amenities. The garden was beautiful and secluded with lots of flowers. A perfect spot for two people.
    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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    Location Information
    Stamford, Connecticut 06903
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Westport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THIS PROPERTY IS AVAILABLE FOR SHORT/LONG TERM RENTALS TO WESTPORT OR PROSPECTIVE WESTPORT RESIDENTS ONLY!! New modern house with roof deck 3 houses from Saugatuck river/bay. Upside down house with 3 bedrooms and master bath on 1st floor. Sun filled living area, kitchen and European wet bath on...
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    Westport, Connecticut 06880
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Easton
    6 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    Pet friendly
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    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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    Easton, Connecticut 06612
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 20
    Easton
    4 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Terrace
    • Central Heating
    • Balcony
    • Patio
    • Grill
    • Housekeeping Included
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our 'Home Away From Home' is an expansive yet cozy and inviting space to hang with family and friends or for a romantic getaway. It is located in the idyllic town of Easton but borders (just 1.5 miles) the charming and thriving town of Fairfield, CT featuring five miles of shoreline on the Long...
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    Location Information
    Easton, Connecticut 06612
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 7
    Southport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Air Conditioning
    • Balcony
    • Parking
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Southport/Westport Border, this spectacular home is ideal for nature lovers who also want to be near every convenience. Very private, charming and serene. Minutes from shopping, restaurants, theater, beaches, galleries, museums, Fairfield marina or Southport Harbor. One mile to Metro-North train...
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    Southport, Connecticut 06890
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    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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    Location Information
    Westport, Connecticut 06880
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 4
    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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    Greenwich, Connecticut 06831
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
    Katonah, NY
    7 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    • Cable/satellite TV
    • Patio
    • Grill
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Totally Restored c.1742 Farmhouse with barn, guesthouse, pool, tennis on over 14 privately owned acres. Privacy, tranquility and views are unmatched. An antique estate with all the modern amenities. Original wide plank hardwood floors and exposed beams. Many period details. A wood-fired pizza oven...
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    Katonah, Westchester County 10536
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 20
    South Salem, NY
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Wi-Fi
    • Housekeeping Included
    • Sauna
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This fully renovated, multiple award-winning lakefront home did inherit an additional floor while keeping the same footprint. Reconstructed on the octagonal foundation of a home that was originally built in 1983, this thoughtfully redesigned and skillfully crafted 3,750 square foot lakeside home...
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    South Salem, Westchester County 10590
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Bedford, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    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
    Valhalla, NY
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located beside the top of the Kensico Dam, with views of Kensico Lake and beautiful walking trails right outside the front door. Beautifully maintained home on private road. Two bedrooms with walk-in closets. King Master suite. Second bedroom features two twin size beds that connect. Home features...
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    Valhalla, Westchester County 10595
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Fairfield
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Grill
    • Washer
    • Ocean Views
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Right across from the beach - penfield and jennings. Easy access for everyone. Amazing 3 br / 2 full bath furnished 1700 sq. Ft. Home on fairfield beach road. Right across the street from the beach! Walk to the train and to town – restaurants, shopping, and theatre. Great alternative to corporate...
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    Fairfield, Connecticut 06824
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Southport
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • 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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    Southport, Connecticut 06890
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Rye, NY
    5 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Internet Access
    • Cable/satellite TV
    • Private Garden
    • Patio
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great for families or temporary corporate accommodation. This 3,000 sq. ft property is only 35 minutes to NYC by Metro-North and 5 walking distance to Rye downtown and the train station. Your family will enjoy from 'Rye Country Club' with swimming pools, tennis, and golf. You can also visit the...
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    Rye, Westchester County 10580
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 8
    Stamford
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you’re looking for a peaceful getaway spent with family then look no further than this 4-bedroom, 2.5-bath home in Stamford! Boasting a spacious English garden and deck to relax on, a fully equipped kitchen to make meals in, and comfortable living spaces to spend time together, this vacation...
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    Stamford, Connecticut 06906
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Valhalla, NY
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Pet friendly
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    About this property
    Private room with all new furniture in ideally located historic home. House has hardwood floors, full kitchen, formal dining area, smart TV in common area, Wi-Fi, cozy bedding, 1.5 baths, and washer/dryer. Kensico Dam, Westchester Medical Center, NY Medical College, Stone Barns Center & Blue Hill...
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    Location Information
    Valhalla, Westchester County 10595
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 2
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