Vacation Rentals & Villas in Wingdale

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50 Houses

    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

    Great rentals within 20 miles that match your search

    Distance approx 19.65 km from Wingdale

      28

      Hudson Valley Cabin - Romantic & Secluded Log Cabin with Private Lake - 85 acres

      New York / Stanfordville

      Stanfordville log cabin

      1 2 2 nights min

      • 1 bedroom
      • sleeps 2
      • 2 nights min

      Price per night from

      $258

      Price per night from

      $258

      Distance approx 19.17 km from Wingdale

        19

        Harley's Hideaway, A Relaxing Escape

        New York / Stanfordville

        Stanfordville apartment

        1 2 1 night min

        • 1 bedroom
        • sleeps 2
        • 1 night min
        • Nearest beach 20 mi
        • Air conditioning
        • Private garden

        Price per night from

        $161

        Price per night from

        $161

        Distance approx 15.38 km from Wingdale

          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

          $859

          Price per night from

          $859

          Distance approx 13.66 km from Wingdale

            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 12.13 km from Wingdale

              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 10.04 km from Wingdale

                8

                Large Private Apartment

                New York / Verbank

                Verbank apartment

                1 3 1 night min

                • 1 bedroom
                • sleeps 3
                • 1 night min
                • Child Friendly

                Price per night from

                $115

                Price per night from

                $115

                Distance approx 7.68 km from Wingdale Show on Map

                (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 8.51 km from Wingdale

                    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 17.75 km from Wingdale

                    (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

                      $916

                      Price per night from

                      $916

                      Distance approx 17.75 km from Wingdale

                      (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 18.71 km from Wingdale

                          19

                          Converted Barn on 5+ Acres. WiFi & Serenity.

                          New York / Clinton Corners

                          Clinton Corners house

                          4 6 7 nights min

                          • 4 bedrooms
                          • sleeps 6
                          • 7 nights min
                          • Child Friendly

                          Price per night from

                          $320

                          Price per night from

                          $320

                          Distance approx 19.28 km from Wingdale

                            16

                            Charming Brick House -Hudson Valley

                            New York / Poughkeepsie

                            Poughkeepsie house

                            3 7 2 nights min

                            • 3 bedrooms
                            • sleeps 7
                            • 2 nights min
                            • Child Friendly
                            • Pet Friendly

                            Price per night from

                            $344

                            Price per night from

                            $344

                            Distance approx 18.79 km from Wingdale

                              12

                              The FarmHouse

                              New York / Millerton

                              Millerton house

                              2 5 120 nights min

                              • 2 bedrooms
                              • sleeps 5
                              • 120 nights min

                              Price per night from

                              $107

                              Price per night from

                              $107

                              Distance approx 18.97 km from Wingdale

                                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

                                $464

                                Price per night from

                                $464

                                Distance approx 7.55 km from Wingdale Show on Map

                                  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 16.08 km from Wingdale

                                    44

                                    1790 Classic Colonial Center Hall home

                                    Connecticut / Sharon

                                    Sharon house

                                    5 11 2 nights min

                                    • 5 bedrooms
                                    • sleeps 11
                                    • 2 nights min
                                    • Child Friendly

                                    Price per night from

                                    $573

                                    Price per night from

                                    $573

                                    Distance approx 7.55 km from Wingdale Show on Map

                                      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 11.38 km from Wingdale

                                      (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 7.55 km from Wingdale Show on Map

                                          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 7.8 km from Wingdale Show on Map

                                            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 12.2 km from Wingdale

                                              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. 13 minutes

                                              Price per night from

                                              $1,145

                                              Distance approx 7.55 km from Wingdale Show on Map

                                                8

                                                Kent Victorian Room 5

                                                Connecticut / Kent

                                                Kent room

                                                2 3 2 nights min

                                                • 2 bedrooms
                                                • sleeps 3
                                                • 2 nights min
                                                • Air conditioning
                                                • Private garden

                                                Price per night from

                                                $182

                                                Price per night from

                                                $182

                                                Distance approx 7.55 km from Wingdale Show on Map

                                                  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 12.39 km from Wingdale

                                                    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 12.39 km from Wingdale

                                                      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

                                                      $378

                                                      Responds fast!
                                                      avg. 54 minutes

                                                      Price per night from

                                                      $378

                                                      Distance approx 12.39 km from Wingdale

                                                        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 6.12 km from Wingdale Show on Map

                                                        (1) Excellent 

                                                          31

                                                          Private Lakefront & Pool DeeLuxGlamping. NYC Getaway

                                                          New York / Pawling

                                                          Pawling camper van

                                                          2 8 1 night min

                                                          • 2 bedrooms
                                                          • sleeps 8
                                                          • 1 night min
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $180

                                                          Price per night from

                                                          $180

                                                          Distance approx 12.39 km from Wingdale

                                                            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

                                                            Responds fast!
                                                            avg. 54 minutes

                                                            Price per night from

                                                            $302

                                                            Distance approx 15.85 km from Wingdale

                                                              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

                                                              $264

                                                              Responds fast!
                                                              avg. 54 minutes

                                                              Price per night from

                                                              $264

                                                              Distance approx 14.32 km from Wingdale

                                                              (1) Excellent 

                                                                11

                                                                Evie's Turning Point Farm

                                                                Connecticut / Warren

                                                                Warren farmhouse

                                                                3 6 2 nights min

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

                                                                Price per night from

                                                                $126

                                                                Price per night from

                                                                $126

                                                                Distance approx 13.65 km from Wingdale

                                                                  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

                                                                  Responds fast!
                                                                  avg. 54 minutes

                                                                  Price per night from

                                                                  $1,002

                                                                  Distance approx 13.4 km from Wingdale

                                                                    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

                                                                    Responds fast!
                                                                    avg. 54 minutes

                                                                    Price per night from

                                                                    $187

                                                                    Distance approx 12.39 km from Wingdale

                                                                      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

                                                                      Responds fast!
                                                                      avg. 54 minutes

                                                                      Price per night from

                                                                      $302

                                                                      Distance approx 12.39 km from Wingdale

                                                                        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

                                                                        Responds fast!
                                                                        avg. 54 minutes

                                                                        Price per night from

                                                                        $302

                                                                        Distance approx 13.87 km from Wingdale

                                                                          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

                                                                          $153

                                                                          Price per night from

                                                                          $153

                                                                          Distance approx 12.39 km from Wingdale

                                                                            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 16.68 km from Wingdale

                                                                              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