We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in New Fairfield, CT and nearby

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    $0
    $318 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Don't let other travelers get your favorite New Fairfield area vacation rental. You're so close to securing your perfect getaway. Book today.
    1 / 24
    New Fairfield
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    1 / 12
    New Fairfield
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    Show Prices
    1 / 23
    New Fairfield
    4 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices

    The following rentals are within 15 miles of New Fairfield, Connecticut.

    1 / 73
    5 of 5 bubbles (10) Excellent
    Pawling, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Parking
    • Porch
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Pawling, New York 12564
    Reviewed March 1, 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 February 20, 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...
    See all reviews
    1 / 20
    5 of 5 bubbles (3) Excellent
    Woodbury
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Balcony
    • Washer
    • Patio
    • Air Conditioning
    • Grill
    • DVD Player
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Woodbury, Connecticut 06798
    Reviewed June 21, 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 for...
    Reviewed June 12, 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...
    See all reviews
    1 / 24
    5 of 5 bubbles (4) Excellent
    New Milford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Patio
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Private Outdoor...
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    New Milford, Connecticut 06776
    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
    See all reviews
    1 / 29
    Wingdale, NY
    4 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • Mountain Views
    • Washer
    • Hot Tub
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wingdale, New York 12594
    1 / 16
    North Salem, NY
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
    other traveler has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Grill
    • Balcony
    • Patio
    • Air Conditioning
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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!... View all property information
    Location Information
    North Salem, Westchester County 10560
    1 / 37
    South Salem, NY
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    South Salem, Westchester County 10606
    1 / 20
    New Milford
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Private Yard
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    New Milford, Connecticut 06776
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    1 / 27
    5 of 5 bubbles (1) Excellent
    Southbury
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travelers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Internet Access
    • Secure Parking
    • Mountain Views
    • Balcony
    • Patio
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Southbury, Connecticut 06488
    Reviewed January 7, 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...
    See all reviews
    1 / 20
    4.5 of 5 bubbles (9) Very good
    Holmes, NY
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Grill
    • Satellite TV
    • Patio
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Holmes, New York 12531
    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...
    See all reviews
    1 / 20
    Carmel, NY
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Patio
    • Washer
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Carmel, New York 10512
    1 / 14
    Ridgefield
    8 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Grill
    • Wi-Fi
    • Satellite TV
    • Parking
    • Air Conditioning
    • Private Yard
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The legendary Sunset Hall has captivated the hearts of its keepers since built for ambassador James Stokes in 1912 at Ridgefield's highest point to afford 50 mile views of the NY skyline and panoramic vistas of Round Pond from the widow walk perch. This regal Georgian has delighted subsequent... View all property information
    Location Information
    Ridgefield, Connecticut 06877
    1 / 26
    Newtown
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Housekeeping...
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    A historic and charming three bedroom, two bath saltbox farmhouse on the grounds of the beautiful and private McLaughlin Vineyards. The house is conveniently located in Northern Fairfield County, about four miles from I-84 and only 90 minutes from mid-town Manhattan. With a large expansive front... View all property information
    Location Information
    Newtown, Connecticut 06482
    1 / 14
    Sherman
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Mountain Views
    • Grill
    • Housekeeping...
    • Waterfront
    • Central Heating
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Sherman, Connecticut 06784
    1 / 28
    Washington
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Private Yard
    • Private Outdoor...
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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,... View all property information
    Location Information
    Washington, Connecticut 06793
    1 / 7
    Roxbury
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Mountain Views
    • Air Conditioning
    • Grill
    • Secure Parking
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Roxbury, Connecticut 06783
    1 / 11
    Southbury
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping...
    • Patio
    • Central Heating
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Southbury, Connecticut 06488
    New Fairfield Flight and Weather Info
    Airports nearby (1)
    Plan your day of travel
    HPN
    Westchester County Airport
    30.1 miles from New Fairfield
    Low airfares recently found by TripAdvisor travelers
    |
    Local Weather
    Powered by Weather Underground
    54° 33°
    April
    63° 42°
    May
    71° 51°
    June

    Top-rated New Fairfield Things to Do

    Browse all things to do

    Additional New Fairfield Info

    View Map
    • Local time: 04:08 AM (EDT)