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Fairfield Holiday Homes

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    All 28 Rentals in Fairfield
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    Fairfield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 30 kilometres of Fairfield.
    Serene Connecticut Retreat - Luxury 2 bedroom apt1 / 42
    (2)Very good
    Stamford
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Westport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    Milford
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Waterfront
    • Grill
    • Washer
    • Patio
    • Internet Access
    • Parking
    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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    New Haven
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    • Terrace
    • Balcony
    • Washer
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy life in an authentic 1900s New England seaside village when you stay in this gorgeous two-bedroom, one-bath home. This Morris Cove corporate housing property is just 10 minutes from downtown New Haven, which means you’re close to Yale Hospital train station, Yale University, and the airport....
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    Location Information
    New Haven, Connecticut 06512
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    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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    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
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    Beach House, Private Beaches, Casinos, Yale U1 / 19
    (10)Excellent
    New Haven
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Ocean Views
    • Cable/satellite TV
    • Porch
    • Grill
    • DVD Player
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 2017
    Great house. Charming. Well equipped with all the necessities. Very clean & quite. Beach is right there. Lanna is a doll. Very kind, accommodating, responsive to texts.
    Reviewed 5 November 2016
    This place was all that we wanted it to be. It was close to the beach (several doors), had a well equipped kitchen, comfy bed. Nice soft absorbent towels, a good shower, washer...
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    About this property
    Charming beach cottage, clean, well maintained interior,central AC. Cottage located on dead end street, 4 houses from LI Sound. Residents share PRIVATE BEACH.Guests of property also have beach rights to adjacent PRIVATE BEACH. View of ocean and salt marsh from front porch. Short walk to TOWN BEACH...
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    Location Information
    New Haven, Connecticut 06512
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Westport
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Private Garden
    • Secure Parking
    • Wi-Fi
    Suitability
    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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    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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    Milford, Connecticut 06460
    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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    Southport, Connecticut 06890
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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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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    Weston, Connecticut 06883
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    East Haven
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Terrace
    • Parking
    • Ocean Views
    • Grill
    • Waterfront
    • Balcony
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated direct beach front house on private beach, beautifully furnished and detailed. All the comforts of home and more! Fully equipped new 'vintage reproduction' kitchen, washing machine and dryer, towels linens, beach chairs, outdoor stove in enclosed screened in porch and cooking area...
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    Location Information
    East Haven, Connecticut 06512
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    We think it's better than the Hamptons.1 / 16
    (9)Very good
    Kings Park, NY
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Grill
    • Air Conditioning
    • Porch
    • Cable/satellite TV
    • Washer
    • Parking
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (PLEASE NOTE: The price shown above is for a stay of one week, seven nights. If you stay two weeks or longer the nightly price is less. If you can only stay at least a minimum of three nights the nightly price is higher. Please inquire by email.) Sit in the shade and watch the birds and boats...
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    Kings Park, Long Island 11754
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    Location Information
    Stamford, Connecticut 06903
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    WATERFRONT BEACH HOUSE - SOUND BEACH1 / 34
    (8)Excellent
    Sound Beach, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Internet Access
    • Waterfront
    • Parking
    • DVD Player
    • Ocean Views
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2017
    My family and I stayed at Shay's Beach House last week. We were pleased to find a cozy home with everything we needed as described. There were 4 adults, and 4 kids aged 6...
    Reviewed 25 July 2017
    I spend my vacation with my family of 4 people at "Waterfront Beach House - Sound Beach” and I assure that it’s everything you want it to be.The House is a dream and the...
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    About this property
    WATERFRONT BEACH HOUSE - SOUND BEACH - Long Island Located on the bluff with amazing views of the Long Island Sound around the year. 1:15 min drive (60 miles) from Manhattan. 25 min. from the Hampton crowd. Weather you're coming to visit family in the area, attending a wedding / event at...
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    Sound Beach, Long Island 11789
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    East Haven
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Grill
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Hobbit House has been newly renovated and appointed to be cozy and comfortable with an antique flair. This property is beautiful inside and out. The beach use for this property is private and your rental of this property comes with everything you need to relax at the beach! This house has the...
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    Location Information
    East Haven, Connecticut 06512
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    East Setauket, NY
    5 Bedrooms, 8 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 great for getting jet skiing, getting a tan or fishing, 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, 8 Bathrooms, Sleeps 10
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    Bridgeport
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    -Prefer Monthly stay. -Entire 2nd fl of HOUSE. 3bedrooms,1Ba,Kitchen,LivRm,Office. -Ideal for Corporate Housing. -CLEAN neat and SAFE with 24HR VIDEO SURVEILLANCE. -Gas stove,microwave,Keurig+Free Coffee, WASHER/DRYER in unit, -FREE WIFI and Steaming Cable, -Private Balcony+OFFICE with desk...
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    Bridgeport, Connecticut 06608
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Milford
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Central Heating
    • Grill
    • DVD Player
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    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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    Milford, Connecticut 06460
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Black Rock~ Fairfield County's hidden gem!1 / 14
    (1)Excellent
    Bridgeport
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2014
    This property is located in a quiet residential location, directly behind one of many small yacht clubs in this area. We found it spacious enough for our family of 2 adults and...
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    About this property
    Enjoy spectacular sunrises and sailing regattas while sipping coffee from the back decks of this charming townhome. Black Rock is a historical peninsula within walking distance to trendy restaurants, tranquil beaches, and Metro North train station with just over an hour ride to New Yok City. Ride...
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    Location Information
    Bridgeport, Connecticut 06605
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Danbury
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Washer
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    • Air Conditioning
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    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Exceptional Waterfront Vacation Home! Located on Connecticut's largest man-made lake, Lake Candlewood. A perfect location for those day trips into NYC either by car or train! Picturesque perennial gardens, stunning lake views & an enticing lakefront w/sand beach, dock & more! A Gracious foyer...
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    Danbury, Connecticut 06811
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    Newtown
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that the homeowner lives onsite, in the separate downstairs 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...
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    Newtown, Connecticut 06470
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    Easton, Connecticut 06612
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 20
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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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    Location Information
    Silver Lane, Connecticut 06460
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Seymour
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Magnificent, fully furnished 1st floor apartment of our 2 story home in one of the best areas of Seymour, CT. Our apartment is for non- smokers only. Very clean and calm. The apartment features a spacious living room with a 2 comfortable futon and one couch, a separate bedroom with queen size bed,...
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    Location Information
    Seymour, Connecticut 06483
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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