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Holiday Homes in Westport

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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 28 Rentals in Westport
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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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    Westport
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 30 kilometres of Westport.
    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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    10580, Rye, Westchester County
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 8
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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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    06903, Stamford, Connecticut
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    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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    06883, Weston, Connecticut
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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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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    • 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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    06460, Silver Lane, Connecticut
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Milford
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Garden
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    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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    06460, Milford, Connecticut
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    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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    06890, Southport, Connecticut
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Greenwich
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
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    • Grill
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    06831, Greenwich, Connecticut
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Greenwich
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
    • Cable/satellite TV
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    • 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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    06830, Greenwich, Connecticut
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Quaint and immaculate 3 br duplex!1 / 26
    (2)Very good
    Greenwich
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Garden
    • Air Conditioning
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    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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    06830, Greenwich, Connecticut
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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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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    10549, Mount Kisco, Westchester County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    11733, East Setauket, Long Island
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    06831, Greenwich, Connecticut
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    06824, Fairfield, Connecticut
    Holiday Rental House - 3 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
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    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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    06460, Milford, Connecticut
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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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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    10560, North Salem, Westchester County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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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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    10576, Pound Ridge, Westchester County
    Holiday Rental House - 1 Bedroom, 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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    06831, Greenwich, Connecticut
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    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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    06612, Easton, Connecticut
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 20
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    Weston
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    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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    06883, Weston, Connecticut
    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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    06460, Milford, Connecticut
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Stamford
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Country Cottage, Kitchen has a stove, microwave, Refig, Double Sink. Living Room, Bedroom, Stiral Staircase to bedrooms, Outside deck, Horses and dogs on property. 7 miles to train station, New York City. 5 Miles to Stamford night life. Walking trails, trout fishing.Very peaceful...
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    06903, Stamford, Connecticut
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Stamford
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Cable/satellite TV
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    • Washer
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    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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    06901, Stamford, Connecticut
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Fairfield
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Internet Access
    • Balcony
    • Hot Tub
    • Cable/satellite TV
    • Waterfront
    • Washer
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Roof Top GetAway' on the Beachfront This renovated Beach House is Perfect for Entertaining and Intimate GetAways The Great Room includes Kitchen & TV Viewing Area w/ FPL and opens to Glass Enclosed Sun Room w/balcony above the beach. The Second level includes two guest bedrooms & Seaside MBR w FPL...
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    06824, Fairfield, Connecticut
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stamford
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • 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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    06901, Stamford, Connecticut
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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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 vacation rental apartment in Newtown. Nestled on the second floor of a fully restored 1890 vintage Victorian...
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    06470, Newtown, Connecticut
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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