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Holiday Rentals in Westport

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    Don't let other travellers get your favourite Westport area holiday home. You're so close to securing your perfect getaway. Book today.
    All 25 Rentals in Westport
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    Westport
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Westport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Westport
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    The following rentals are within 30 kilometres of Westport.
    Mount Kisco, NY
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Patio
    • Washer
    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *  Pets allowed with a pet fee of $250 and please ask management *. Pool heating available for $45 a day No car needed - Mount Kisco train station less than 10 minutes away with Uber and Taxis waiting Situated at the end of a quiet, semi-private road, this delightful Country...
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    Location Information
    Mount Kisco, Westchester County 10549
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    #2 - Your own place on the Beach near Silver Sands Park1 / 16
    (1)Excellent
    Silver Lane
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Washer
    • Wi-Fi
    • Central Heating
    • Private Garden
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 October 2017
    OMG!! The pictures do not show this place justice. This is a wanderful place to kick back and enjoy yourself and sit on the couch and have coffee while seeing the ocean. Take a...
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    About this property
    Come relax or enjoy a beach community. The entire 2nd floor apartment is available for you and your guests - 2 BRs, 1BA, sleeps 4 adults or a family of 4. Convenient to Yale and I-95. Take the opportunity to explore Silver Sands State Park, restaurants and dining. Have a BBQ in the private...
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    Silver Lane, Connecticut 06460
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    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
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    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
    Premiere beach property1 / 14
    (2)Excellent
    Milford
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Terrace
    • Private Garden
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 April 2019
    This was by far one of the best stays we have stayed at in the last several years. Home is immaculate, all linens are provided, it’s cozy and the owner Mary was an amazing host...
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    About this property
    Our home is located in beautiful Woodmont Beach and sits directly across the street from the water. Main floor of the house has a full kitchen for cooking, dining area with table and 6 chairs living room with L shaped sofa and flat screen tv, one bedroom with queen bed, two night stands and a six...
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    Milford, Connecticut 06460
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    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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    Amenities & Details
    • 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
    Charming and immaculate 3 br duplex!1 / 24
    (8)Excellent
    Greenwich
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Washer
    • Parking
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 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 19 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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    Location Information
    Greenwich, Connecticut 06830
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    East Setauket, NY
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Ocean Views
    • Wi-Fi
    • DVD Player
    • Grill
    • Washer
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A wonderful summer getaway with stunning waterfront views, a few steps away from private beach access. This house sits on 2 full acres of land with steps leading down to the beach thats great for getting jet skiing, fishing, and secluded from the busy streets of Long Island. Including a full...
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    East Setauket, Long Island 11733
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Milford
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The first floor apartment is bright, sunny and airy. The beach is right across the street with unobstructed views of Charles Island. You can also walk right over to a seasonal Greek restaurant next door, or to Silver Sands State Park for more recreational activities. We are right next door if you...
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    Location Information
    Milford, Connecticut 06460
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Serene Connecticut Retreat - Luxury 2 bedroom apt1 / 21
    (3)Very good
    Stamford
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    Stamford, Connecticut 06903
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Weston
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Grill
    • Patio
    • Air Conditioning
    • 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
    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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    Easton, Connecticut 06612
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 20
    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
    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
    New Canaan
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Garden
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Recently renovated by the homeowners, this spacious main level of a 2 family ranch has everything you could want. With 3 bedrooms, two full bathrooms and a brand new full kitchen, this home can comfortably sleep 6. Additionally, there is an office, where you can work remotely, and when you are...
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    New Canaan, Connecticut 06903
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    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
    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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    Location Information
    Katonah, Westchester County 10536
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 20
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    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
    • 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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    Location Information
    Bedford, Westchester County 10506
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    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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    Location Information
    Rye, Westchester County 10580
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 8
    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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    Location Information
    Southport, Connecticut 06890
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Greenlawn, NY
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
    • Patio
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful room in quiet Huntington, NY. -Most comfortable king-sized bed -desk with laptop, pens & note pads - shared bathroom & kitchen w/fridge space, microwave, stove, cooking utensils. -Relaxing backyard with patio seating -5-10 drive to everything( Gyms, Malls, Hwys to NYC & LIRR). Driveway...
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    Location Information
    Greenlawn, Long Island 11743
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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