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76 Houses

    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

    $343

    Price per night from

    $343

    Great rentals within 20 miles that match your search

    Distance approx 16.97 km from Poughkeepsie

    (1) Excellent 

      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

      $257

      Price per night from

      $257

      Distance approx 9.82 km from Poughkeepsie

      (16) Excellent 

        4

        Eclectic One Bedroom Cottage in the Hudson Valley

        New York / New Paltz

        New Paltz cottage

        1 3 1 night min

        • 1 bedroom
        • sleeps 3
        • 1 night min
        • Ask about children
        • Air conditioning
        • Pet Friendly

        Price per night from

        $171

        Responds fast!
        avg. 2 hours 42 minutes

        Price per night from

        $171

        Distance approx 16.39 km from Poughkeepsie

          8

          The Wiltwyck Guest House

          New York / Kingston

          Kingston b and b

          1 2 1 night min

          • 1 bedroom
          • sleeps 2
          • 1 night min
          • Child Friendly
          • Air conditioning

          Price per night from

          $91

          Price per night from

          $91

          Distance approx 3.9 km from Poughkeepsie Show on Map

            45

            Black Creek Bed and Breakfast (Reclaimed Room w/Shared Bathroom)

            New York / Highland

            Highland b and b

            1 2 1 night min

            • 1 bedroom
            • sleeps 2
            • 1 night min
            • Air conditioning

            Price per night from

            $256

            Price per night from

            $256

            Distance approx 3.9 km from Poughkeepsie Show on Map

              45

              Black Creek Bed and Breakfast (Arbor Room w/Shared Bathroom)

              New York / Highland

              Highland b and b

              1 2 1 night min

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

              Price per night from

              $251

              Price per night from

              $251

              Distance approx 9.74 km from Poughkeepsie

                18

                1880s HUDSON VALLEY NEW PALTZ CATSKILLS FARMHOUSE BEAUTIFULLY FURNiSHED POOL

                New York / Rifton

                Rifton house

                3 6 3 nights min

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

                Price per night from

                $513

                Price per night from

                $513

                Distance approx 12.98 km from Poughkeepsie

                  38

                  Amazing Holiday Home

                  New York / New Paltz

                  New Paltz house

                  3 8 3 nights min

                  • 3 bedrooms
                  • sleeps 8
                  • 3 nights min
                  • Beach / lakeside relaxation
                  • Swimming pool
                  • Child Friendly

                  Price per night from

                  $969

                  Price per night from

                  $969

                  Distance approx 15.85 km from Poughkeepsie

                    14

                    PineTop

                    New York / Cold Spring

                    Cold Spring house

                    5 9 2 nights min

                    • 5 bedrooms
                    • sleeps 9
                    • 2 nights min
                    • Swimming pool
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $855

                    Responds fast!
                    avg. 2 hours 16 minutes

                    Price per night from

                    $855

                    Distance approx 14.75 km from Poughkeepsie

                    (5) Excellent 

                      14

                      DeMew House in Historic Rondout

                      New York / Kingston

                      Kingston house

                      1 4 2 nights min

                      • 1 bedroom
                      • sleeps 4
                      • 2 nights min
                      • Air conditioning
                      • Private garden

                      Price per night from

                      $200

                      Price per night from

                      $200

                      Distance approx 17.21 km from Poughkeepsie

                      (1) Excellent 

                        17

                        Orchard home

                        Catskill Region / Kerhonkson

                        Kerhonkson house

                        3 6 2 nights min

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

                        Price per night from

                        $286

                        Price per night from

                        $286

                        Distance approx 17.15 km from Poughkeepsie

                          35

                          THE STABLES IN THE CARRIAGE HOUSE

                          New York / Kingston

                          Kingston villa

                          1 2 2 nights min

                          • 1 bedroom
                          • sleeps 2
                          • 2 nights min
                          • Nearest beach 5 mi
                          • Car not necessary
                          • Air conditioning

                          Price per night from

                          $257

                          Price per night from

                          $257

                          Distance approx 11.13 km from Poughkeepsie

                          (2) Excellent 

                            26

                            romantig house at magical lake

                            New York / Ulster Park

                            Ulster Park house

                            2 5 2 nights min

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

                            Price per night from

                            $285

                            Responds fast!
                            avg. 1 hour 13 minutes

                            Price per night from

                            $285

                            Distance approx 11.17 km from Poughkeepsie

                              9

                              Mirror Lake Cabins Ulster Park New York

                              New York / Ulster Park

                              Ulster Park bungalow

                              1 2 2 nights min

                              • 1 bedroom
                              • sleeps 2
                              • 2 nights min
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $143

                              Price per night from

                              $143

                              Distance approx 14.8 km from Poughkeepsie

                              (2) Average 

                                26

                                Charming Rhinebeck carriage barn, Hudson valley

                                Rhinebeck / Hudson Valley

                                Rhinebeck cottage

                                1 4 2 nights min

                                • 1 bedroom
                                • sleeps 4
                                • 2 nights min
                                • Beach / lakeside relaxation
                                • Private garden

                                Price per night from

                                $200

                                Price per night from

                                $200

                                Distance approx 12.33 km from Poughkeepsie

                                  31

                                  Newly Renovated Rosendale Getaway

                                  New York / Rosendale

                                  Rosendale apartment

                                  2 4 1 night min

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

                                  Price per night from

                                  $115

                                  Price per night from

                                  $115

                                  Distance approx 16.39 km from Poughkeepsie

                                    14

                                    Antique Stone House

                                    New York / Kingston

                                    Kingston b and b

                                    1 2 1 night min

                                    • 1 bedroom
                                    • sleeps 2
                                    • 1 night min
                                    • Child Friendly

                                    Price per night from

                                    $172

                                    Price per night from

                                    $172

                                    Distance approx 14.46 km from Poughkeepsie

                                      1

                                      Base Camp - Dutch Colonial Estate

                                      New York / Beacon

                                      Beacon apartment

                                      1 2 2 nights min

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

                                      Price per night from

                                      $257

                                      Price per night from

                                      $257

                                      Distance approx 18.58 km from Poughkeepsie

                                      (2) Excellent 

                                        8

                                        Modern, Eclectic, Tranquil Mountain Retreat

                                        New York / Gardiner

                                        Gardiner house

                                        3 6 3 nights min

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

                                        Price per night from

                                        $286

                                        Price per night from

                                        $286

                                        Distance approx 9.12 km from Poughkeepsie

                                          20

                                          Perfect New Paltz Location

                                          New York / New Paltz

                                          New Paltz house

                                          3 8 2 nights min

                                          • 3 bedrooms
                                          • sleeps 8
                                          • 2 nights min
                                          • Child Friendly
                                          • Air conditioning
                                          • Private garden

                                          Price per night from

                                          $343

                                          Price per night from

                                          $343

                                          Distance approx 10.17 km from Poughkeepsie

                                          (1) Excellent 

                                            44

                                            for the creative spirit, lightfilled loft house

                                            New York / Ulster Park

                                            Ulster Park studio

                                            Studio 3 2 nights min

                                            • Studio
                                            • sleeps 3
                                            • 2 nights min
                                            • Child Friendly

                                            Price per night from

                                            $285

                                            Responds fast!
                                            avg. 1 hour 13 minutes

                                            Price per night from

                                            $285

                                            Distance approx 15.97 km from Poughkeepsie

                                              32

                                              Summer or Summer Monthly Swimming Lake Rhinebeck Oasis

                                              New York / Rhinebeck

                                              Rhinebeck house

                                              3 8 30 nights min

                                              • 3 bedrooms
                                              • sleeps 8
                                              • 30 nights min
                                              • Child Friendly
                                              • Pet Friendly

                                              Price per night from

                                              $267

                                              Price per night from

                                              $267

                                              Distance approx 18.46 km from Poughkeepsie

                                              (4) Excellent 

                                                19

                                                50 Mins from Manhattan River view

                                                Cornwall / Cornwall on Hudson

                                                Cornwall on Hudson house

                                                5 17 min stay varies

                                                • 5 bedrooms
                                                • sleeps 17
                                                • min stay varies
                                                • Beach / lakeside relaxation
                                                • Swimming pool
                                                • Child Friendly
                                                “Spectacular view” We loved this house. It has probably the best view of the Hudson River. The house was very comfortable and had everything we needed. Susan was very helpful with information about the sights and restaurants. We will definitely be

                                                Price per night from

                                                $1,508

                                                Responds fast!
                                                avg. 2 hours 46 minutes

                                                Price per night from

                                                $1,508

                                                Distance approx 13.18 km from Poughkeepsie

                                                (4) Excellent 

                                                  43

                                                  Fiddlers Farmhouse

                                                  New York / Rhinebeck

                                                  Rhinebeck farmhouse

                                                  3 6 2 nights min

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

                                                  Price per night from

                                                  $401

                                                  Price per night from

                                                  $401

                                                  Distance approx 3.9 km from Poughkeepsie Show on Map

                                                    45

                                                    Black Creek Bed and Breakfast

                                                    New York / Highland

                                                    Highland house

                                                    4 8 1 night min

                                                    • 4 bedrooms
                                                    • sleeps 8
                                                    • 1 night min
                                                    • Air conditioning

                                                    Price per night from

                                                    $1,143

                                                    Price per night from

                                                    $1,143

                                                    Distance approx 3.9 km from Poughkeepsie Show on Map

                                                      45

                                                      Black Creek Bed and Breakfast (Zen Room w/Shared Bathroom)

                                                      New York / Highland

                                                      Highland b and b

                                                      1 2 1 night min

                                                      • 1 bedroom
                                                      • sleeps 2
                                                      • 1 night min
                                                      • Air conditioning

                                                      Price per night from

                                                      $286

                                                      Price per night from

                                                      $286

                                                      Distance approx 15.44 km from Poughkeepsie

                                                        36

                                                        Wild Mountain Getaway - sleeps +20

                                                        New York / Gardiner

                                                        Gardiner house

                                                        5 24 min stay varies

                                                        • 5 bedrooms
                                                        • sleeps 24
                                                        • min stay varies
                                                        • Swimming pool
                                                        • Child Friendly
                                                        • Air conditioning

                                                        Price per night from

                                                        $1,145

                                                        Price per night from

                                                        $1,145

                                                        Distance approx 16.39 km from Poughkeepsie

                                                          12

                                                          Antique Stone House

                                                          New York / Kingston

                                                          Kingston b and b

                                                          1 2 1 night min

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

                                                          Price per night from

                                                          $258

                                                          Price per night from

                                                          $258

                                                          Distance approx 8.6 km from Poughkeepsie

                                                            26

                                                            NEW! Apartment on 10 Acres w/ Catskill Mtns Views!

                                                            New York / Tillson

                                                            Tillson apartment

                                                            2 6 min stay varies

                                                            • 2 bedrooms
                                                            • sleeps 6
                                                            • min stay varies
                                                            • Ski
                                                            • Child Friendly
                                                            • Air conditioning

                                                            Price per night from

                                                            $212

                                                            Responds fast!
                                                            avg. 40 minutes

                                                            Price per night from

                                                            $212

                                                            Distance approx 3.9 km from Poughkeepsie Show on Map

                                                              45

                                                              Black Creek Bed and Breakfast (Paris Room w/Shared Bathroom)

                                                              New York / Highland

                                                              Highland b and b

                                                              1 2 1 night min

                                                              • 1 bedroom
                                                              • sleeps 2
                                                              • 1 night min
                                                              • Air conditioning

                                                              Price per night from

                                                              $287

                                                              Price per night from

                                                              $287

                                                              Distance approx 19.85 km from Poughkeepsie

                                                              (8) Excellent 

                                                                21

                                                                Enchanting Cottage In The Woods

                                                                New York / Accord

                                                                Accord cottage

                                                                3 8 2 nights min

                                                                • 3 bedrooms
                                                                • sleeps 8
                                                                • 2 nights min
                                                                • Beach / lakeside relaxation
                                                                • Swimming pool
                                                                • Child Friendly
                                                                “Peaceful Getaway” A group of childhood friends, our spouses, and my young child just completed a visit to this lovely cottage. We had a wonderful time in the peaceful and beautiful Catskills -- hiked at Minnewaska State park, biked on the O&W; Rail Tr

                                                                Price per night from

                                                                $441

                                                                Price per night from

                                                                $441

                                                                Distance approx 15.33 km from Poughkeepsie

                                                                (2) Excellent 

                                                                  30

                                                                  Spacious Rhinebeck Village House w/ Lavish Decor!

                                                                  New York / Rhinebeck

                                                                  Rhinebeck house

                                                                  7 10 min stay varies

                                                                  • 7 bedrooms
                                                                  • sleeps 10
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Ski
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $745

                                                                  Responds fast!
                                                                  avg. 40 minutes

                                                                  Price per night from

                                                                  $745

                                                                  Distance approx 14.72 km from Poughkeepsie

                                                                  (2) Very Good 

                                                                    12

                                                                    Keith's Classic Film Retreat

                                                                    New York / Newburgh

                                                                    Newburgh b and b

                                                                    2 4 1 night min

                                                                    • 2 bedrooms
                                                                    • sleeps 4
                                                                    • 1 night min
                                                                    • Child Friendly
                                                                    • Car not necessary
                                                                    • Air conditioning

                                                                    Price per night from

                                                                    $114

                                                                    Price per night from

                                                                    $114

                                                                    Distance approx 3.12 km from Poughkeepsie Show on Map

                                                                      15

                                                                      Nature Lovers Getaway

                                                                      New York / Highland

                                                                      Highland house

                                                                      3 6 7 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 6
                                                                      • 7 nights min
                                                                      • Child Friendly
                                                                      • Ask about pets

                                                                      Price per night from

                                                                      $172

                                                                      Responds fast!
                                                                      avg. 5 minutes

                                                                      Price per night from

                                                                      $172

                                                                      Distance approx 12.55 km from Poughkeepsie

                                                                      (19) Excellent 

                                                                        21

                                                                        Renovated Schoolhouse - Hudson Valley Getaway

                                                                        New York / New Paltz

                                                                        New Paltz cottage

                                                                        2 7 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 7
                                                                        • min stay varies
                                                                        • Child Friendly
                                                                        • Car not necessary
                                                                        • Air conditioning
                                                                        “Schoolhouse cottage is an idyllic retreat.” We travelled to the area for a respite from New York City with our two young children. The cottage was perfect for our needs - clean, quiet, well-appointed, and with activities galore for the children. We

                                                                        Price per night from

                                                                        $121

                                                                        Responds fast!
                                                                        avg. 3 hours 46 minutes

                                                                        Price per night from

                                                                        $121

                                                                        Distance approx 8.63 km from Poughkeepsie

                                                                          25

                                                                          Dutchess County Guest House on Working Horse Farm!

                                                                          New York / Salt Point

                                                                          Salt Point house

                                                                          3 6 min stay varies

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

                                                                          Price per night from

                                                                          $321

                                                                          Responds fast!
                                                                          avg. 40 minutes

                                                                          Price per night from

                                                                          $321

                                                                          Distance approx 9.99 km from Poughkeepsie

                                                                            29

                                                                            The Yellow Dutch Cottage

                                                                            New York / Ulster Park

                                                                            Ulster Park house

                                                                            3 6 2 nights min

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

                                                                            Price per night from

                                                                            $487

                                                                            Price per night from

                                                                            $487

                                                                            Distance approx 9.2 km from Poughkeepsie

                                                                              24

                                                                              Cozy New Paltz House w/ Views of Shawangunk Ridge!

                                                                              New York / New Paltz

                                                                              New Paltz house

                                                                              1 2 min stay varies

                                                                              • 1 bedroom
                                                                              • sleeps 2
                                                                              • min stay varies

                                                                              Price per night from

                                                                              $98

                                                                              Responds fast!
                                                                              avg. 40 minutes

                                                                              Price per night from

                                                                              $98