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Westport Holiday Rentals

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    Don't let other travellers get your favourite Westport area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 27 Rentals in Westport
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    Westport
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Westport
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 30 kilometres of Westport.
    Serene Connecticut Retreat - Luxury 2 bedroom apt1 / 21
    (3)Very good
    Stamford
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Mount Kisco, NY
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • 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 provide a sense of seclusion, yet the wide-open space allows for wandering eyes to breathe in the stunning views of...
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    Mount Kisco, Westchester County 10549
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Charming and immaculate 3 br duplex!1 / 23
    (7)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 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...
    Reviewed 6 January 2015
    I stayed here with my family for 5 days in new year's eve, because we wanted to be near Manhattan but in a quiet, nice and safe location. It was exactly what we needed! Very...
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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
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    #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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    Amenities & Details
    • 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
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    Greenwich
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Private Garden
    • Secure Parking
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Greenwich, Connecticut 06831
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Quaint and immaculate 3 br duplex!1 / 30
    (2)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 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
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    Greenwich
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    Stamford
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At Prospect Street Apartments, more is always better. Featuring high-rise apartment buildings surrounding a contemporary atrium, Prospect Street Apartments are the place to live in downtown Stamford. Our apartment homes will redefine your standard of living. Interior features include hardwood...
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    Stamford, Connecticut 06901
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Stamford
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The fabulous apartments at The Blvd offer resident spectacular features like fully-equipped kitchens, spacious closets, hardwood flooring and much more. A furnished sky terrace with outdoor grills & fire pits, a lounge & screening room and a 24 hour fitness center are some of the fantastic...
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    Stamford, Connecticut 06901
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Weston
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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
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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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    Milford
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • 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
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    East Setauket, NY
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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
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    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
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    Stamford
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At Prospect Street Apartments, more is always better. Featuring high-rise apartment buildings surrounding a contemporary atrium, Prospect Street Apartments are the place to live in downtown Stamford. Our apartment homes will redefine your standard of living. Interior features include hardwood...
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    Location Information
    Stamford, Connecticut 06901
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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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    Greenwich, Connecticut 06831
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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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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    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, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The fabulous apartments at The Blvd offer resident spectacular features like fully-equipped kitchens, spacious closets, hardwood flooring and much more. A furnished sky terrace with outdoor grills & fire pits, a lounge & screening room and a 24 hour fitness center are some of the fantastic...
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    Location Information
    Stamford, Connecticut 06901
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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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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    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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    Milford
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Central Heating
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A spectacular direct waterfront home with the modern conveniences! Wake to the sounds of surf and breath taking sunrises. Relax and dine on the deck with grill. The home is naturally cooled by sea breezes or, there is also air conditioning, if you prefer. The beach house has 2 bedrooms, and 3 full...
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    Location Information
    Milford, Connecticut 06460
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Milford
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience a classic New England beach vacation from this gorgeous 4-bedroom, 1-bathroom vacation rental cottage in Milford that comfortably sleeps 4 adults,7 people total. With a private beach, a fire pit, and an outdoor shower all just beyond your front door, this home offers guests plenty of...
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    Milford, Connecticut 06460
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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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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    Easton, Connecticut 06612
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 20
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    Newtown
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Central Heating
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that the homeowner lives onsite, in the separate unit, and may be present during your stay ** Have a comfortable stay with your closest friends at this 1-bedroom, 1-bath apartment in Newtown. Nestled on the second floor of a fully restored 1890 vintage Victorian home, this unit...
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    Newtown, Connecticut 06470
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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