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56 Houses

    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. 40 minutes

    Price per night from

    $229

    (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

      Great rentals within 20 miles that match your search

      Distance approx 4.5 km from New Preston

        36

        100% ROXBURY (Zoom in Map+) PoshPadsCT "PAINTER RIDGE" Mint 3BR, Pool, BBQ,Bikes

        Connecticut / Washington

        Washington house

        3 8 min stay varies

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

        Price per night from

        $262

        Responds fast!
        avg. 54 minutes

        Price per night from

        $262

        Distance approx 7.32 km from New Preston

          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 14.72 km from New Preston

          (3) Very Good 

            22

            Comfortable Rustic Cottage on 4 Wooded Acres with Brook

            Connecticut / West Cornwall

            West Cornwall cottage

            2 6 2 nights min

            • 2 bedrooms
            • sleeps 6
            • 2 nights min
            • Nearest beach 12 mi
            • Child Friendly
            • Air conditioning

            Price per night from

            $171

            Price per night from

            $171

            Distance approx 1.36 km from New Preston

              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

              $263

              Responds fast!
              avg. 54 minutes

              Price per night from

              $263

              Distance approx 4.41 km from New Preston

                30

                PoshPadsCT "South Street" 4-BR Cottage with Heated Pool

                Connecticut / Washington

                Washington house

                4 8 min stay varies

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

                Price per night from

                $793

                Price per night from

                $793

                Distance approx 15.67 km from New Preston

                  4

                  Exclusive Rental in Beautiful Amenia!

                  New York / Amenia

                  Amenia house

                  3 6 30 nights min

                  • 3 bedrooms
                  • sleeps 6
                  • 30 nights min
                  • Swimming pool
                  • Child Friendly
                  • Air conditioning

                  Price per night from

                  $152

                  Price per night from

                  $152

                  Distance approx 1.36 km from New Preston

                    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

                    $263

                    Responds fast!
                    avg. 54 minutes

                    Price per night from

                    $263

                    Distance approx 6.27 km from New Preston

                      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

                      $400

                      Price per night from

                      $400

                      Distance approx 4.67 km from New Preston

                        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

                        $263

                        Responds fast!
                        avg. 54 minutes

                        Price per night from

                        $263

                        Distance approx 15.84 km from New Preston

                          16

                          Direct Waterfront Lake Home on Tranquil Harwinton

                          Connecticut / Harwinton

                          Harwinton cottage

                          2 4 3 nights min

                          • 2 bedrooms
                          • sleeps 4
                          • 3 nights min
                          • Child Friendly
                          • Air conditioning
                          • Pet Friendly

                          Price per night from

                          $257

                          Responds fast!
                          avg. 2 hours 47 minutes

                          Price per night from

                          $257

                          Distance approx 1.65 km from New Preston

                            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

                            $1,143

                            Responds fast!
                            avg. 40 minutes

                            Price per night from

                            $1,143

                            Distance approx 10.15 km from New Preston

                            (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

                              $286

                              Price per night from

                              $286

                              Distance approx 10.29 km from New Preston

                                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

                                Price per night from

                                $228

                                Distance approx 7.32 km from New Preston

                                  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 13.73 km from New Preston

                                    13

                                    Quiet Country Contemporary Home on 5 Private Acres

                                    Connecticut / West Cornwall

                                    West Cornwall house

                                    3 10 2 nights min

                                    • 3 bedrooms
                                    • sleeps 10
                                    • 2 nights min
                                    • Nearest beach 6 mi
                                    • Child Friendly
                                    • Air conditioning

                                    Price per night from

                                    $463

                                    Price per night from

                                    $463

                                    Distance approx 1.36 km from New Preston

                                      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

                                      $301

                                      Responds fast!
                                      avg. 54 minutes

                                      Price per night from

                                      $301

                                      Distance approx 1.36 km from New Preston

                                        42

                                        100% WASHINGTON! (Zoom in Map++) PoshPadsCT "SUNNY RIDGE" 8-BR Estate, Pool, BBQ

                                        Washington / Washington Depot

                                        Washington Depot house

                                        8 16 min stay varies

                                        • 8 bedrooms
                                        • sleeps 16
                                        • min stay varies
                                        • Child Friendly

                                        Price per night from

                                        $377

                                        Responds fast!
                                        avg. 54 minutes

                                        Price per night from

                                        $377

                                        Distance approx 1.36 km from New Preston

                                          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

                                          $301

                                          Responds fast!
                                          avg. 54 minutes

                                          Price per night from

                                          $301

                                          Distance approx 7.32 km from New Preston

                                            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 7.35 km from New Preston

                                            (1) Excellent 

                                              14

                                              Wits End Farm B&B

                                              Connecticut / Bethlehem

                                              Bethlehem b and b

                                              5 10 4 nights min

                                              • 5 bedrooms
                                              • sleeps 10
                                              • 4 nights min
                                              • Child Friendly

                                              Price per night from

                                              $914

                                              Price per night from

                                              $914

                                              Distance approx 12.98 km from New Preston

                                                28

                                                Guest Cottage on Country Estate

                                                Connecticut / Watertown

                                                Watertown house

                                                3 6 min stay varies

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

                                                Price per night from

                                                $134

                                                Responds fast!
                                                avg. 17 minutes

                                                Price per night from

                                                $134

                                                Distance approx 7.32 km from New Preston

                                                  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 19.63 km from New Preston

                                                  (1) Excellent 

                                                    13

                                                    Lake House

                                                    Connecticut / Lakeville

                                                    Lakeville house

                                                    5 9 2 nights min

                                                    • 5 bedrooms
                                                    • sleeps 9
                                                    • 2 nights min
                                                    • Child Friendly
                                                    • Pet Friendly

                                                    Price per night from

                                                    $686

                                                    Price per night from

                                                    $686

                                                    Distance approx 15.03 km from New Preston

                                                    (1) Excellent 

                                                      27

                                                      Quiet Getaway in Historic Village

                                                      Connecticut / Southbury

                                                      Southbury house

                                                      2 6 min stay varies

                                                      • 2 bedrooms
                                                      • sleeps 6
                                                      • min stay varies
                                                      • Nearest beach 3 mi
                                                      • Child Friendly
                                                      • Car not necessary

                                                      Price per night from

                                                      $171

                                                      Price per night from

                                                      $171

                                                      Distance approx 1.36 km from New Preston

                                                        22

                                                        100% WASHINGTON! (Zoom in Map ++) PoshPadsCT "SHEARER RD" Mint 3BR, Pool, BBQ

                                                        Washington / Washington Depot

                                                        Washington Depot house

                                                        3 6 min stay varies

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

                                                        Price per night from

                                                        $225

                                                        Responds fast!
                                                        avg. 54 minutes

                                                        Price per night from

                                                        $225

                                                        Distance approx 7.35 km from New Preston

                                                          24

                                                          Prana Residence - Spa

                                                          Connecticut / Cornwall Bridge

                                                          Cornwall Bridge house

                                                          3 7 2 nights min

                                                          • 3 bedrooms
                                                          • sleeps 7
                                                          • 2 nights min
                                                          • Swimming pool
                                                          • Ask about children
                                                          • Air conditioning

                                                          Price per night from

                                                          $857

                                                          Price per night from

                                                          $857

                                                          Distance approx 18.73 km from New Preston

                                                          (1) Excellent 

                                                            11

                                                            Riverwood - Cozy Carriage House in the Woods

                                                            Connecticut / Falls Village

                                                            Falls Village apartment

                                                            1 2 2 nights min

                                                            • 1 bedroom
                                                            • sleeps 2
                                                            • 2 nights min
                                                            • Ask about children
                                                            • Air conditioning
                                                            • Private garden

                                                            Price per night from

                                                            $257

                                                            Price per night from

                                                            $257

                                                            Distance approx 15.06 km from New Preston

                                                            (6) Excellent 

                                                              12

                                                              Quiet first floor apartment in Torrington

                                                              Connecticut / Torrington

                                                              Torrington apartment

                                                              1 2 2 nights min

                                                              • 1 bedroom
                                                              • sleeps 2
                                                              • 2 nights min

                                                              Price per night from

                                                              $103

                                                              Price per night from

                                                              $103

                                                              Distance approx 9.93 km from New Preston

                                                                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

                                                                $714

                                                                Price per night from

                                                                $714

                                                                Distance approx 4.5 km from New Preston

                                                                  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

                                                                  Responds fast!
                                                                  avg. 54 minutes

                                                                  Price per night from

                                                                  $340

                                                                  Distance approx 1.36 km from New Preston

                                                                    18

                                                                    100%WashingtonZOOM MAP+PoshPadsCT "Magical Barn"

                                                                    Washington / Washington Depot

                                                                    Washington Depot house

                                                                    5 10 min stay varies

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

                                                                    Price per night from

                                                                    $340

                                                                    Responds fast!
                                                                    avg. 54 minutes

                                                                    Price per night from

                                                                    $340

                                                                    Distance approx 7.35 km from New Preston

                                                                    (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 18.09 km from New Preston

                                                                        26

                                                                        The Birches at Cascade Mountain Winery: 4 bedrooms, sleeps 10, pet friendly!

                                                                        New York / Amenia

                                                                        Amenia house

                                                                        4 10 min stay varies

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

                                                                        Price per night from

                                                                        $430

                                                                        Price per night from

                                                                        $430

                                                                        Distance approx 11.33 km from New Preston

                                                                          28

                                                                          NEW! Goshen Home w/Deck 5 Mi. from Mohawk Mountain

                                                                          Connecticut / Goshen

                                                                          Goshen house

                                                                          4 8 min stay varies

                                                                          • 4 bedrooms
                                                                          • sleeps 8
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Ski
                                                                          • Child Friendly

                                                                          Price per night from

                                                                          $264

                                                                          Responds fast!
                                                                          avg. 40 minutes

                                                                          Price per night from

                                                                          $264

                                                                          Distance approx 1.36 km from New Preston

                                                                            38

                                                                            100% ROXBURY! PoshPadsCT "NORTH ST" Private, Mint 6-BR, Pool,Views, Fire Pl, BBQ

                                                                            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

                                                                            $264

                                                                            Responds fast!
                                                                            avg. 54 minutes

                                                                            Price per night from

                                                                            $264

                                                                            Distance approx 13.97 km from New Preston

                                                                              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. 40 minutes

                                                                              Price per night from

                                                                              $287