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46 Houses

    24

    Unique New Fairfield House w/ Deck & Lake Views!

    Connecticut / New Fairfield

    New Fairfield house

    3 10 min stay varies

    • 3 bedrooms
    • sleeps 10
    • min stay varies
    • Child Friendly
    • Air conditioning

    Price per night from

    $287

    Responds fast!
    avg. 33 minutes

    Price per night from

    $287

    Great rentals within 20 miles that match your search

    Distance approx 16.01 km from New Fairfield

      15

      LUXURY COTTAGE

      Westchester County / Pound Ridge

      Pound Ridge cottage

      1 4 2 nights min

      • 1 bedroom
      • sleeps 4
      • 2 nights min
      • Ask about children
      • Ask about pets

      Price per night from

      $315

      Responds fast!
      avg. 2 hours 6 minutes

      Price per night from

      $315

      Distance approx 14.79 km from New Fairfield

        29

        Lake House Rental On Your Own Private Lake

        New York / Wingdale

        Wingdale villa

        4 11 4 nights min

        • 4 bedrooms
        • sleeps 11
        • 4 nights min
        • Beach / lakeside relaxation
        • Child Friendly
        • Air conditioning

        Price per night from

        $716

        Price per night from

        $716

        Distance approx 15.18 km from New Fairfield

        (5) Excellent 

          24

          Its the Perfect Weekend House just 80min from NYC!

          Connecticut / Woodbury

          Woodbury house

          4 8 min stay varies

          • 4 bedrooms
          • sleeps 8
          • min stay varies
          • Beach / lakeside relaxation
          • Air conditioning
          • Private garden

          Price per night from

          $172

          Responds fast!
          avg. 2 hours 57 minutes

          Price per night from

          $172

          Distance approx 19.48 km from New Fairfield

            10

            Spectacular Lake House

            New York / Putnam Valley

            Putnam Valley house

            3 6 30 nights min

            • 3 bedrooms
            • sleeps 6
            • 30 nights min
            • Child Friendly
            • Air conditioning
            • Private garden

            Price per night from

            $418

            Price per night from

            $418

            Distance approx 11.71 km from New Fairfield

              32

              Lake House with Indoor Spa, 1 hour from Manhattan

              New York / Carmel

              Carmel house

              3 6 2 nights min

              • 3 bedrooms
              • sleeps 6
              • 2 nights min
              • Child Friendly

              Price per night from

              $229

              Price per night from

              $229

              Distance approx 12.22 km from New Fairfield

              (1) Excellent 

                27

                Quiet Getaway in Historic Village

                Connecticut / Southbury

                Southbury house

                2 6 1 night min

                • 2 bedrooms
                • sleeps 6
                • 1 night min
                • Nearest beach 3 mi
                • Child Friendly
                • Car not necessary

                Price per night from

                $182

                Price per night from

                $182

                Distance approx 16.8 km from New Fairfield

                  24

                  Lakefront New Preston Cottage w/Dock & Fire Pit!

                  Connecticut / New Preston

                  New Preston cottage

                  3 6 min stay varies

                  • 3 bedrooms
                  • sleeps 6
                  • min stay varies
                  • Child Friendly
                  • Pet Friendly

                  Price per night from

                  $229

                  Responds fast!
                  avg. 47 minutes

                  Price per night from

                  $229

                  Distance approx 11.31 km from New Fairfield

                  (9) Very Good 

                    20

                    Lake Bliss the Perfect Getaway

                    New York / Holmes

                    Holmes house

                    3 10 1 night min

                    • 3 bedrooms
                    • sleeps 10
                    • 1 night min
                    • Beach / lakeside relaxation
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $250

                    Price per night from

                    $250

                    Distance approx 14.21 km from New Fairfield

                      30

                      South Street 4-BR Cottage with Heated Pool

                      Connecticut / Washington

                      Washington house

                      4 8 2 nights min

                      • 4 bedrooms
                      • sleeps 8
                      • 2 nights min
                      • Swimming pool
                      • Child Friendly
                      • Air conditioning

                      Price per night from

                      $796

                      Price per night from

                      $796

                      Distance approx 16.95 km from New Fairfield

                        42

                        Spectacular Modern Home Near NYC

                        Connecticut / Weston

                        Weston house

                        5 8 2 nights min

                        • 5 bedrooms
                        • sleeps 8
                        • 2 nights min
                        • Child Friendly
                        • Air conditioning

                        Price per night from

                        $1,025

                        Responds fast!
                        avg. 1 hour 49 minutes

                        Price per night from

                        $1,025

                        Distance approx 10.22 km from New Fairfield

                        (4) Excellent 

                          36

                          20'x40' inground private pool just for you&house with 4bedrooms

                          Connecticut / New Milford

                          New Milford house

                          4 8 7 nights min

                          • 4 bedrooms
                          • sleeps 8
                          • 7 nights min
                          • Beach / lakeside relaxation
                          • Nearest beach 13 mi
                          • Swimming pool
                          “Wonderful experience!!!” My wife and our two children (10 and 7)spent a wonderful time at this beautiful New Milford retreat. The house was spacious and nicely decorated and we loved the privacy of the place. You couldn't see any neighbors and yet sho
                          …see more

                          Price per night from

                          $328

                          Responds fast!
                          avg. 1 hour 40 minutes

                          Price per night from

                          $328

                          Distance approx 6.11 km from New Fairfield Show on Map

                            14

                            Lake Cottage with Views and Fireplace

                            Connecticut / Sherman

                            Sherman house

                            2 5 2 nights min

                            • 2 bedrooms
                            • sleeps 5
                            • 2 nights min
                            • Beach / lakeside relaxation
                            • Child Friendly

                            Price per night from

                            $228

                            Responds fast!
                            avg. 1 hour 16 minutes

                            Price per night from

                            $228

                            Distance approx 12.18 km from New Fairfield

                              12

                              A Historic Home for Guests and Lawns/Facilities for Gatherings such as Weddings

                              Connecticut / Southbury

                              Southbury house

                              3 8 1 night min

                              • 3 bedrooms
                              • sleeps 8
                              • 1 night min
                              • Air conditioning
                              • Private garden

                              Price per night from

                              $228

                              Price per night from

                              $228

                              Distance approx 17.36 km from New Fairfield

                              (1) Excellent 

                                16

                                Wits End Farm

                                Connecticut / Bethlehem

                                Bethlehem house

                                6 12 3 nights min

                                • 6 bedrooms
                                • sleeps 12
                                • 3 nights min
                                • Nearest beach 3 mi
                                • Swimming pool
                                • Child Friendly

                                Price per night from

                                $1,031

                                Price per night from

                                $1,031

                                Distance approx 9.13 km from New Fairfield

                                  24

                                  Victorian Newtown Apt w/Fire Pit 20 Mi to Jennings

                                  Connecticut / Newtown

                                  Newtown apartment

                                  1 4 min stay varies

                                  • 1 bedroom
                                  • sleeps 4
                                  • min stay varies
                                  • Ski

                                  Price per night from

                                  $161

                                  Responds fast!
                                  avg. 33 minutes

                                  Price per night from

                                  $161

                                  Distance approx 18.27 km from New Fairfield

                                    8

                                    Kent Victorian Room 3

                                    Connecticut / Kent

                                    Kent room

                                    1 2 2 nights min

                                    • 1 bedroom
                                    • sleeps 2
                                    • 2 nights min
                                    • Air conditioning
                                    • Private garden

                                    Price per night from

                                    $171

                                    Price per night from

                                    $171

                                    Distance approx 18.07 km from New Fairfield

                                      5

                                      Adorable Guest Cottage

                                      Connecticut / Weston

                                      Weston cottage

                                      2 4 1 night min

                                      • 2 bedrooms
                                      • sleeps 4
                                      • 1 night min
                                      • Child Friendly

                                      Price per night from

                                      $178

                                      Price per night from

                                      $178

                                      Distance approx 15.94 km from New Fairfield

                                      (1) Excellent 

                                        23

                                        Rhubarb Hill, a Charming 1850's Farmhouse

                                        Connecticut / New Preston

                                        New Preston house

                                        3 6 3 nights min

                                        • 3 bedrooms
                                        • sleeps 6
                                        • 3 nights min
                                        • Child Friendly
                                        • Car not necessary
                                        • Pet Friendly

                                        Price per night from

                                        $401

                                        Price per night from

                                        $401

                                        Distance approx 18.27 km from New Fairfield

                                          8

                                          Kent Victorian Room 2

                                          Connecticut / Kent

                                          Kent room

                                          1 2 2 nights min

                                          • 1 bedroom
                                          • sleeps 2
                                          • 2 nights min
                                          • Air conditioning
                                          • Private garden

                                          Price per night from

                                          $171

                                          Price per night from

                                          $171

                                          Distance approx 18.27 km from New Fairfield

                                            8

                                            Kent Victorian Room 4

                                            Connecticut / Kent

                                            Kent room

                                            1 2 2 nights min

                                            • 1 bedroom
                                            • sleeps 2
                                            • 2 nights min
                                            • Air conditioning
                                            • Private garden

                                            Price per night from

                                            $126

                                            Price per night from

                                            $126

                                            Distance approx 10.1 km from New Fairfield

                                              29

                                              Very private,4bdrm house,20x40inground pool, pool house. Paradise!

                                              Connecticut / New Milford

                                              New Milford house

                                              4 8 3 nights min

                                              • 4 bedrooms
                                              • sleeps 8
                                              • 3 nights min
                                              • Child Friendly

                                              Price per night from

                                              $401

                                              Price per night from

                                              $401

                                              Distance approx 17.72 km from New Fairfield

                                                25

                                                Lakefront Warren 'Carriage House' on 25 Acres!

                                                Connecticut / Warren

                                                Warren house

                                                7 14 4 nights min

                                                • 7 bedrooms
                                                • sleeps 14
                                                • 4 nights min
                                                • Ski
                                                • Child Friendly
                                                • Air conditioning

                                                Price per night from

                                                $1,145

                                                Responds fast!
                                                avg. 37 minutes

                                                Price per night from

                                                $1,145

                                                Distance approx 15.92 km from New Fairfield

                                                  24

                                                  100%WASHINGTON! Zoom In Map PoshPadsCT"Calhoun" 4BR, Views!,Meadows,Pool,25Acres

                                                  Washington / Washington Depot

                                                  Washington Depot house

                                                  4 8 min stay varies

                                                  • 4 bedrooms
                                                  • sleeps 8
                                                  • min stay varies
                                                  • Child Friendly
                                                  • Pet Friendly

                                                  Price per night from

                                                  $264

                                                  Price per night from

                                                  $264

                                                  Distance approx 15.92 km from New Fairfield

                                                    39

                                                    100% ROXBURY! (Zoom in Map++) PoshPadsCT "SENTRY HILL"Mint 6BR Pool,4 FirePlaces

                                                    Washington / Washington Depot

                                                    Washington Depot house

                                                    6 12 min stay varies

                                                    • 6 bedrooms
                                                    • sleeps 12
                                                    • min stay varies
                                                    • Child Friendly
                                                    • Pet Friendly

                                                    Price per night from

                                                    $302

                                                    Price per night from

                                                    $302

                                                    Distance approx 15.92 km from New Fairfield

                                                      28

                                                      100% ROXBURY! (Zoom in Map++) PoshPadsCT "MOOSEHORN" Mint 5BR Pool, BBQ, Bikes

                                                      Washington / Washington Depot

                                                      Washington Depot house

                                                      5 12 min stay varies

                                                      • 5 bedrooms
                                                      • sleeps 12
                                                      • min stay varies
                                                      • Nearest beach 7 mi
                                                      • Swimming pool
                                                      • Child Friendly

                                                      Price per night from

                                                      $302

                                                      Price per night from

                                                      $302

                                                      Distance approx 18.56 km from New Fairfield

                                                        21

                                                        Washington - "Senff 8-BR Estate" Heated Pool, Private Scenic Estate Neighborhood

                                                        Connecticut / Washington

                                                        Washington house

                                                        8 14 min stay varies

                                                        • 8 bedrooms
                                                        • sleeps 14
                                                        • min stay varies
                                                        • Nearest beach 5 mi
                                                        • Swimming pool
                                                        • Child Friendly

                                                        Price per night from

                                                        $340

                                                        Price per night from

                                                        $340

                                                        Distance approx 15.92 km from New Fairfield

                                                          36

                                                          100% ROXBURY! (Zoom Map In++) PoshPadsCT "PAINTER HILL" Mint 4-BR,Pool,Fire,BBQ

                                                          Washington / Washington Depot

                                                          Washington Depot house

                                                          4 14 min stay varies

                                                          • 4 bedrooms
                                                          • sleeps 14
                                                          • min stay varies
                                                          • Child Friendly
                                                          • Pet Friendly

                                                          Price per night from

                                                          $264

                                                          Price per night from

                                                          $264

                                                          Distance approx 18.27 km from New Fairfield

                                                            6

                                                            Kent Victorian Room 1

                                                            Connecticut / Kent

                                                            Kent room

                                                            1 2 2 nights min

                                                            • 1 bedroom
                                                            • sleeps 2
                                                            • 2 nights min
                                                            • Air conditioning
                                                            • Private garden

                                                            Price per night from

                                                            $182

                                                            Price per night from

                                                            $182

                                                            Distance approx 14.65 km from New Fairfield

                                                              12

                                                              Washington - "Kirby Road" 3-Bedroom Carriage House on the Green - PoshPadsCT

                                                              Connecticut / Washington

                                                              Washington house

                                                              3 6 min stay varies

                                                              • 3 bedrooms
                                                              • sleeps 6
                                                              • min stay varies
                                                              • Child Friendly
                                                              • Air conditioning
                                                              • Private garden

                                                              Price per night from

                                                              $187

                                                              Price per night from

                                                              $187

                                                              Distance approx 18.34 km from New Fairfield

                                                                14

                                                                Washington "Shearer" 3-Bedroom Country Cottage - PoshPadsCT

                                                                Connecticut / Washington

                                                                Washington house

                                                                3 7 min stay varies

                                                                • 3 bedrooms
                                                                • sleeps 7
                                                                • min stay varies
                                                                • Child Friendly
                                                                • Air conditioning
                                                                • Pet Friendly

                                                                Price per night from

                                                                $773

                                                                Price per night from

                                                                $773

                                                                Distance approx 14.75 km from New Fairfield

                                                                  18

                                                                  Washington "Plumb Hill" 5-Bedroom, Heated Pool, PoshPadsCT

                                                                  Connecticut / Washington

                                                                  Washington house

                                                                  5 10 min stay varies

                                                                  • 5 bedrooms
                                                                  • sleeps 10
                                                                  • min stay varies
                                                                  • Nearest beach 5 mi
                                                                  • Swimming pool
                                                                  • Child Friendly

                                                                  Price per night from

                                                                  $264

                                                                  Price per night from

                                                                  $264

                                                                  Distance approx 15.92 km from New Fairfield

                                                                    34

                                                                    100% WASHINGTON! (Zoom in Map++) PoshPadsCT "51 SENFF RD" Mint 5BR, Pool, BBQ

                                                                    Washington / Washington Depot

                                                                    Washington Depot house

                                                                    5 10 min stay varies

                                                                    • 5 bedrooms
                                                                    • sleeps 10
                                                                    • min stay varies
                                                                    • Child Friendly
                                                                    • Pet Friendly

                                                                    Price per night from

                                                                    $302

                                                                    Price per night from

                                                                    $302

                                                                    Distance approx 11.39 km from New Fairfield

                                                                      17

                                                                      Roxbury "Judd's Bridge" 5-BR with Heated Pool, PoshPadsCT

                                                                      Connecticut / Roxbury

                                                                      Roxbury house

                                                                      4 10 min stay varies

                                                                      • 4 bedrooms
                                                                      • sleeps 10
                                                                      • min stay varies
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $1,002

                                                                      Price per night from

                                                                      $1,002

                                                                      Distance approx 12.24 km from New Fairfield

                                                                        8

                                                                        Library Bed Room with Fireplace, Dressing Room and Separate Entry from outside

                                                                        Connecticut / Southbury

                                                                        Southbury room

                                                                        1 2 2 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 2
                                                                        • 2 nights min
                                                                        • Private garden

                                                                        Price per night from

                                                                        $103

                                                                        Price per night from

                                                                        $103

                                                                        Distance approx 6.07 km from New Fairfield Show on Map

                                                                        (1)  

                                                                          32

                                                                          Must Love Garden and the Sound of Stream

                                                                          New York / Lanesville

                                                                          Lanesville house

                                                                          4 9 1 night min

                                                                          • 4 bedrooms
                                                                          • sleeps 9
                                                                          • 1 night min
                                                                          • Child Friendly
                                                                          • Pet Friendly

                                                                          Price per night from

                                                                          $287

                                                                          Price per night from

                                                                          $287

                                                                          Distance approx 13.51 km from New Fairfield

                                                                            20

                                                                            LAKEFRONT COTTAGE ON PRISTINE LAKE

                                                                            New York / Carmel

                                                                            Carmel cottage

                                                                            2 4 7 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 4
                                                                            • 7 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Ask about children
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $225

                                                                            Price per night from

                                                                            $225

                                                                            Distance approx 11.55 km from New Fairfield

                                                                              7

                                                                              2 Bedroom Suite with Kitchen

                                                                              Connecticut / Roxbury

                                                                              Roxbury hotel apartment

                                                                              2 4 1 night min

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • 1 night min
                                                                              • Child Friendly
                                                                              • Air conditioning
                                                                              • Private garden

                                                                              Price per night from

                                                                              $286

                                                                              Price per night from

                                                                              $286