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Holiday Homes in Fairfield

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    Don't let other travellers get your favourite Fairfield area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 26 Rentals in Fairfield
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    Fairfield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Fairfield
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 30 kilometres of Fairfield.
    Jamaica Court Cottage1 / 19
    (10)Excellent
    New Haven
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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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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    06512, New Haven, Connecticut
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    06460, Silver Lane, Connecticut
    Condo/Apartment - 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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    06880, Westport, Connecticut
    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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    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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    06460, Milford, Connecticut
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    Serene Connecticut Retreat - Luxury 2 bedroom apt1 / 21
    (2)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 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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    Westport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Patio
    • Ocean Views
    • Air Conditioning
    • Waterfront
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located directly on Long Island Sound in the residential section of Saugatuck Shores, this recently renovated, completely furnished, 3 bedroom, 2 bathroom house offers wide unobstructed views of the water from the front porch and the second floor deck. It has new stainless kitchen appliances, new...
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    06880, Westport, Connecticut
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    06890, Southport, Connecticut
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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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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    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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    East Haven
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    • Ocean Views
    • Cable/satellite TV
    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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    06512, East Haven, Connecticut
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
    06512, East Haven, Connecticut
    Holiday Rental House - 4 Bedrooms, 2 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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    Seymour
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our apartment is very comfortable for people who come to our area an extended period. We have everything for a long stay: fully furnished 1st floor apartment features a spacious living room with two futons and one couch, a separate bedroom with a comfortable queen size bed, a full eat-in-kitchen...
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    06483, Seymour, Connecticut
    Holiday Rental House - 1 Bedroom, 1 Bathroom, 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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    06460, Milford, Connecticut
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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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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    06883, Weston, 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
    • 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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    06901, Stamford, Connecticut
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    New Haven
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious 3 open bedrooms are available in a 2 floor open house close to Yale University. This beautiful open floor house features beautifully designed 2 open bedrooms(no walls/doors), open kitchen with gas stove, dishwasher, and a microwave. Has custom built-in furniture, lots of storage and...
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    06511, New Haven, Connecticut
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    06612, Easton, Connecticut
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 20
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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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    06880, Westport, Connecticut
    Holiday Rental House - 4 Bedrooms, 3 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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    Location Information
    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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    Location Information
    06470, Newtown, Connecticut
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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
    06903, Stamford, Connecticut
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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