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New Fairfield Vacation Rentals

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    All 25 Rentals in New Fairfield
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    New Fairfield
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    The following rentals are within 15 miles of New Fairfield.
    Its the Perfect Weekend House just 80min from NYC!1 / 19
    (5)Excellent
    Woodbury
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Quiet Getaway in Historic Village1 / 27
    (1)Excellent
    Southbury
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Carmel, NY
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Waterfront
    • Grill
    • Hot Tub
    • Central Heating
    • Washer
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Secluded and serene lake house located located in private community at the end of a private road (second to last house on the block) within the Carmel Hamlet with indoor spa room, wood-burning fireplace in the front living room and a gas fireplace which is located in the large den. The gas fire...
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    Carmel, New York 10512
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    20'x40' inground private pool just for you&house with 4bedrooms1 / 36
    (4)Excellent
    New Milford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 10, 2014
    This is a spacious 4 bedroom property. it is high above the local road and is surrounded by trees. Neighbours are a good distance away, so the loudest sounds are from the local...
    Reviewed July 21, 2014
    A spectacular week in a secluded spot and yet minutes from quaint New Milford Village. Pool is GREAT
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    About this property
    LITCHFIELD COUNTY, New Milford, CONNECTICUT Beautiful!! very private country setting; four bedrooms, large family room with cathedral ceilings and grand piano. All amenities: cable TV, CD, DVD,VCR, internet and air conditioning. Deck--including a screen house; gas grill. 20x40 inground pool with...
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    New Milford, Connecticut 06776
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Southbury
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Housekeeping Included
    • Wi-Fi
    • Mountain Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    There are two ways of renting: THE HOUSE RENTAL which can be for short terms or up to six months. The house is the largest and most spacious of the homes remaining in the historic Village of South Britain. It was built in 1795 at the zenith of its industrial factories producing as much or more...
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    Southbury, Connecticut 06488
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Wingdale, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • DVD Player
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    • Mountain Views
    • Washer
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get away from it all in this vacation home on private lake and nature preserve nestled in the foothills of the Berkshires. Perched on a peninsula on the shores of Lake Weil (viewable via Google map), this stunning 4-bedroom contemporary home offers exclusive use of your own 30-acre lake. Pack a...
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    Wingdale, New York 12594
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    Sherman
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Washer
    • Mountain Views
    • Grill
    • Housekeeping Included
    • Waterfront
    • Central Heating
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private secure community with million dollar homes. Perfect weekend retreat. 90 minutes from NYC. This two bedroom cottage has all the necessary amenities. Includes access to two private beaches on Candlewood Lake and Green Pond. Just renovated with new wood floors, new appliances, new...
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    Sherman, Connecticut 06784
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Private Lakefront & Pool DeeLuxGlamping. NYC Getaway1 / 31
    (1)Excellent
    Pawling, NY
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Private Outdoor Pool (Heated)
    • Mountain Views
    • Waterfront
    • Air Conditioning
    • Private Yard
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 3, 2017
    Love the place. It was great for our family. Very spacious and clean. The place is also located in a great area so it was perfect. We will rent it again next year for our...
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    About this property
    You will have full access to this 2 bedroom camper that sleeps 8. We are located on a private/quiet road. This is not a camp ground. You will be the only family staying with us. We have a huge in ground salt water system pool that you will have full access to. We live here on the grounds, so the...
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    Pawling, New York 12564
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    New Milford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our house has a soul. It is not like a fancy hotel but instead all elements of decor have some story to tell. The indoor is painted by an artist. We have grand piano which if you know how to play will make time together more fun. The pool is just amazing. Deep end has 8' and shallow 4.5'.We love it...
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    Location Information
    New Milford, Connecticut 06776
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Roxbury
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Yard
    • Mountain Views
    • Air Conditioning
    • Grill
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The best way to experience Roxbury Connecticut... A completely Private Apartment in Modern contemporary home located on Route 67 in Roxbury Connecticut. 2 Bedrooms, Full Kitchen, Full Bathroom, Living Room, Oversized Deck, Outdoor Grill, and 3+ Acres of Land with Outdoor Seating. Close to...
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    Roxbury, Connecticut 06783
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Carmel, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Washer
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Secluded lakefront cottage w/ private dock on China Pond in the Sedgewood Club One hour drive from Upper Westside. Enjoy swimming and fishing in pristine spring fed waters (no motorboats). Private golf course (no tee times) and clay tennis courts available on Club premises. Charming Adirondack...
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    Location Information
    Carmel, New York 10512
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Southbury
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Yard
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will be staying in a house that was built in 1795. It is as it was built, except for the modern kitchen and baths. You'll share the house with the Architect Owner and a possible guest in The Artist's Studio and Bed Room unless your party takes both bedrooms. Enjoy the living and dining rooms...
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    Location Information
    Southbury, Connecticut 06488
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 2
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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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    Location Information
    Newtown, Connecticut 06470
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Lake Bliss the Perfect Getaway1 / 20
    (9)Very good
    Holmes, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 16, 2016
    Review received! Just one more thing to do…We have received your review for Property #141424 Once you confirm it, we can work on getting it live! Read the review below; if...
    Reviewed July 6, 2016
    Great little getaway for the weekend. Really enjoyed the lake, the barbecue, and the canoes. There isn't much else to do, so a long vacation may not be the best idea. I think an...
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    About this property
    Fully furnished gorgeous home directly on beautiful Whaley Lake only 1-1½ hours from New York City. Two levels each with full kitchen and bath. Washer & dryer, wireless internet, plenty of parking. The units can be rented separately or together. Lower level with huge panoramic windows overlooking...
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    Location Information
    Holmes, New York 12531
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Roxbury
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Meticulously restored country house on scenic dirt road in historic Roxbury near Washington town line. Barn, small pond, stream on a great flat dirt road perfect for walking, jogging, biking. 5 minutes to the Mayflower Inn & Spa and Washington Center and Steeprock Preserve. Close to Lake...
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    Location Information
    Roxbury, Connecticut 06783
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Washington Depot
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are searching for the perfect country escape, Shaker Modern is for you! Set on 11 groomed hill-top acres, this meticulously restored home overlooks and abuts the Steep Rock Land Preserve on the Washington/Roxbury border. This light and airy mint home has 6 bedrooms and 4.5 marble bathrooms,...
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    Washington Depot, Washington 06794
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Washington Depot
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of Washington in the best location, this renovated cottage is perched on 25-acres offering total privacy and spectacular 270-degree views. The home has a perfect entertaining terrace wit a gas barbecue and a heated infinity waterfall pool. The first story has 3 bedrooms, a...
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    Washington Depot, Washington 06794
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Washington Depot
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private Mint 5-Bedroom, 4-Bath Country Estate in one of Washington's Best neighborhoods surrounded by large estates. Heated pool, trampoline, game room, gas bbq, 2 gas fireplaces. A short drive to the Mayflower Inn & Spa and other Washington Restaurants, Galleries, Shops and Litchfield Shopping and...
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    Washington Depot, Washington 06794
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Washington Depot
    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunny Ridge Farm is a magnificent country estate on 14 acres in the Sunny Ridge Historic District. It is the largest home (17,000 SF) in Washington, the most exclusive town in rural Litchfield County. The estate has been meticulously restored and has almost every possible amenity - 8 over sized...
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    Washington Depot, Washington 06794
    Rental Home - 8 Bedrooms, 7 Bathrooms, Sleeps 16
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    Washington Depot
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect 6BR 3.5 Bath 4 Fire-Place home with heated pool and child's play gym on a scenic country dirt road that leads into a land preserve along the Shepaug River - perfect for walking, jogging, biking. The most desirable rural historic location within 2 hours of NYC - Roxbury and Washington CT....
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    Washington Depot, Washington 06794
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    Washington Depot
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Private Yard
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very Large 4300 SF Single-Family 5-Bedroom home with heated pool, large eat-in kitchen plus second kitchen, high ceilings, 2 fireplaces, best Roxbury quiet (no parties, events, multi-person shares) estate neighborhood surrounded by land preserves overlooking a pond and across from a hundred-acre...
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    Washington Depot, Washington 06794
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Washington Depot
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    If you are searching for the perfect country setting within an easy drive to wonderful local restaurants, spas, shopping, antiquing, skiing, water activities, hiking, historic homes and museums, then Country Cottage is for you. Wonderful family activities such as apple picking, farm stands, country...
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    Washington Depot, Washington 06794
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Washington Depot
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    About this property
    Luxury exceptional design 4 Bedroom home in the best Roxbury location with firepaces and heated pool. Fully restored with a luxury kitchen, great room porch, den with a sleeper sofa, 4 bedrooms, 4 full bathrooms. Frette sheets, bathrobes, linens, down feather beds, comforters and pillows. Flat...
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    Washington Depot, Washington 06794
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Washington Depot
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the best historic walking/biking/running neighborhood in Washington! Pristine barn-style home, 5 bedrooms, 4 wood-burning fireplaces, pool, giant terrace with gas bbq set in an apple orchard with a heated pool. The gourmet kitchen is fully equipped with a Viking 6-burner gas range and...
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    Location Information
    Washington Depot, Washington 06794
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    29.8 miles from New Fairfield
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