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New Fairfield Holiday Rentals

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    Don't let other travellers get your favourite New Fairfield area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 22 Rentals in New Fairfield
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    Exclusive High End Candlewood Lake retreat1 / 21
    (6)Excellent
    New Fairfield
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    CANDLE WOOD ISLE LAKE HOUSE   EARLY SPRING GETAWAY  LOW RATES1 / 23
    (5)Excellent
    New Fairfield
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Beautiful Candlewood Isle Rental- Great Family Gathering Spot1 / 24
    (15)Excellent
    New Fairfield
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Beautiful Candlewood Isle Cottage With Spectacular Lake Views.1 / 12
    (9)Excellent
    New Fairfield
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Internet Access
    • Parking
    • Patio
    • Air Conditioning
    • Satellite TV
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    New Fairfield, Connecticut 06812
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    The following rentals are within 25 kilometres of New Fairfield.
    Its the Perfect Weekend House just 80min from NYC!1 / 23
    (3)Excellent
    Woodbury
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Balcony
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    • DVD Player
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 June 2015
    We came to Woodbury to meet as a family & acknowledge the passing of our father in the town we all grew up in. Douglas was extremely helpful and encouraging in our arranging...
    Reviewed 12 June 2015
    This property is conveniently located near I84 and the restaurants/shops of Woodbury and Southbury, Conn. It is a beautiful house with a fully equipped kitchen, washer/dryer...
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    About this property
    This four bedroom antique, photograph, and sculpture filled, light-splashed two story home on Connecticut's Antique Trail has spacious indoor and outdoor lounging areas in a beautiful acre private garden setting three minutes from Woodbury's historic town center. Even better its only one minute...
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    Woodbury, Connecticut 06798
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    Private Lakefront & Pool DeeLuxGlamping. NYC Getaway1 / 31
    (1)Excellent
    Pawling, NY
    2 Bedrooms, 1 Bathroom, Sleeps 12 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
    • Mountain Views
    • Waterfront
    • Air Conditioning
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 September 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 12. 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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 12
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    Pawling 1900 house near Darryl house,Thunder ridge1 / 73
    (11)Excellent
    Pawling, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Parking
    • Porch
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 March 2017
    We had booked this home for a group of girl friend attending a show at Daryl's House. We all loved the house it was charming and quaint but also very comfortable, spotlessly...
    Reviewed 20 February 2017
    Great house! Cute town within walking distance. The house is so comfortable you may not want to go out! If we go back to Pawling, I'd definitely stay here again. I highly...
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    About this property
    Historic beauty built in 1900 in the heart of the village Town of Pawling only a 90 min metro north train ride from Manhattan and no need for a car you can walk to the house and to most things or take a local taxi if needed for places outside of the village. .. Short walk to Metro North train(2...
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    Pawling, New York 12564
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Roxbury
    4 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Housekeeping Included
    • Washer
    • Central Heating
    • Balcony
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great for families or reunions! We love small groups. Through Karina arrange a catered meal and relax from hustle and care. Soak up the history and beauty in a place that resonates with centuries of community and warmth. Beyond the pool, an ice house reminds us of life before electricity. A...
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    Location Information
    Roxbury, Connecticut 06783
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 11
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    New Milford
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1840 completely renovated country house with lots of room, convenience and quietness. 4,000 sq. ft. furnished with many antiques. A most unique country kitchen, formal dining room, eat-in kitchen, library, living room, den, five bedrooms (some have 'Sleep Number' mattresses), and 5 and a half...
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    Location Information
    New Milford, Connecticut 06776
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Wingdale, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Waterfront
    • 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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    Location Information
    Wingdale, New York 12594
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    Danbury
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Patio
    • DVD Player
    • 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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    Location Information
    Danbury, Connecticut 06811
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    20'x40' inground private pool just for you&house with 4bedrooms1 / 24
    (4)Excellent
    New Milford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Patio
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 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 21 July 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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    Location Information
    New Milford, Connecticut 06776
    Holiday Rental House - 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 Garden
    • Mountain Views
    • Air Conditioning
    • Grill
    • Secure Parking
    • Wi-Fi
    • 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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    Location Information
    Roxbury, Connecticut 06783
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    Location Information
    Sherman, Connecticut 06784
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Washington
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Private Garden
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    South Street is a mint condition 4 bedroom home with a heated pool, wonderful flat private quiet yard with a swing set far back from the street. The home is in Washington, the most desirable historic rural town in Litchfield County with wonderful restaurants, land preserves, private schools,...
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    Location Information
    Washington, Connecticut 06793
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    North Salem, NY
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • 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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    Brewster, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Balcony
    • DVD Player
    • Patio
    • Washer
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My precious cottage is located in a wonderful private lake community. The cottage has the perfect deck to enjoy morning sunshine and a terrific covered deck to enjoy the evening sunset. The living room have a cathedral ceiling and plenty of windows, the morning light streams in to brighten every...
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    Location Information
    Brewster, New York 10509
    Holiday Rental House - 2 Bedrooms, 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
    • Satellite TV
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 September 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 6 July 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Carmel, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Air Conditioning
    • DVD Player
    • 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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    • Washer
    • Internet Access
    • Secure Parking
    • Mountain Views
    • Balcony
    • Patio
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 January 2015
    My husband and I, and our doggies, enjoyed the Coach House so much. We became friends with the owner who was very accomodating. He even loaned us his ornaments, so we could...
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    About this property
    Charming, recently renovated, two-story, 1,200 square-foot coach house built in 1795 and set in a tranquil 3-acres of lawns, gardens, orchards and forest at the heart of the historic Village of South Britain founded in 1715 by settlers from the south of England, This vacation home an hour and a...
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    Location Information
    Southbury, Connecticut 06488
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Southbury
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Patio
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is in a historic village with 22 others clustered around the Congregational Church across the street from the house. Built in 1795 it has four large corner rooms on both floors On the first floor there's a central entry hall, with dining and library to either side, straight ahead are...
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    Location Information
    Southbury, Connecticut 06488
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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