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80 Houses

(2) Excellent 

    36

    Secluded Country Getaway

    New York / Highland

    Highland house

    2 6 2 nights min

    • 2 bedrooms
    • sleeps 6
    • 2 nights min
    • Nearest beach 31 mi
    • Swimming pool
    • Child Friendly

    Price per night from

    $132

    Responds fast!
    avg. 2 hours 18 minutes

    Price per night from

    $132

      57

      Hudson Valley Villa - Modern Masterpiece Cantilevered Over Hudson River Bluff

      New York / Highland

      Highland house

      4 8 3 nights min

      • 4 bedrooms
      • sleeps 8
      • 3 nights min
      • Nearest beach 14 mi
      • Swimming pool
      • Child Friendly

      Price per night from

      $1,369

      Responds fast!
      avg. 29 minutes

      Price per night from

      $1,369

        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

          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

          $287

          Price per night from

          $287

            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

            $286

            Price per night from

            $286

              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

              $286

              Price per night from

              $286

                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

                $258

                Price per night from

                $258

                  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

                  $1,145

                  Price per night from

                  $1,145

                  (12) Excellent 

                    18

                    Hudson Valley 40 Acres With Lake And Hiking

                    New York / Highland

                    Highland house

                    4 12 2 nights min

                    • 4 bedrooms
                    • sleeps 12
                    • 2 nights min
                    • Child Friendly
                    • Air conditioning
                    • Private garden

                    Price per night from

                    $628

                    Responds fast!
                    avg. 29 minutes

                    Price per night from

                    $628

                    Great rentals within 20 miles that match your search

                    Distance approx 14.17 km from Highland

                      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 15.28 km from Highland

                      (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

                        $762

                        Responds fast!
                        avg. 3 hours 2 minutes

                        Price per night from

                        $762

                        Distance approx 16.7 km from Highland

                        (2) Excellent 

                          25

                          Carriage House on private English Tudor Estate

                          New York / Kingston

                          Kingston house

                          1 2 2 nights min

                          • 1 bedroom
                          • sleeps 2
                          • 2 nights min
                          • Nearest beach 5 mi
                          • Air conditioning

                          Price per night from

                          $229

                          Price per night from

                          $229

                          Distance approx 11.25 km from Highland

                          (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
                            …see more

                            Price per night from

                            $121

                            Responds fast!
                            avg. 3 hours 46 minutes

                            Price per night from

                            $121

                            Distance approx 19.71 km from Highland

                              40

                              Peaceful & Secluded Olive Star Cottage IN OLIVEBRIDGE NY (MAP ERROR BY Tripadvs)

                              New York / Olivebridge

                              Olivebridge house

                              2 4 min stay varies

                              • 2 bedrooms
                              • sleeps 4
                              • min stay varies
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $205

                              Price per night from

                              $205

                              Distance approx 16.27 km from Highland

                                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

                                $879

                                Responds fast!
                                avg. 2 hours 16 minutes

                                Price per night from

                                $879

                                Distance approx 14.64 km from Highland

                                (12) Excellent 

                                  14

                                  The Gallery Inn-A loft style accommodation near the waterfront in Kingston NY

                                  New York / Kingston

                                  Kingston apartment

                                  1 4 min stay varies

                                  • 1 bedroom
                                  • sleeps 4
                                  • min stay varies
                                  • Beach / lakeside relaxation
                                  • Nearest beach 2 mi
                                  • Ask about children
                                  “Submerged in art!” We absolutely loved our stay at the Gallery Inn! The space was beautifully renovated, yet comfortable and homey. Terrific artwork decorates the walls. The location is amazing, just steps away from the Hudson River and the fantast
                                  …see more

                                  Price per night from

                                  $189

                                  Responds fast!
                                  avg. 1 hour 14 minutes

                                  Price per night from

                                  $189

                                  Distance approx 14.63 km from Highland

                                    9

                                    Des Artistes Master Bedroom at Church Des Artistes

                                    New York / Kingston

                                    Kingston b and b

                                    1 2 1 night min

                                    • 1 bedroom
                                    • sleeps 2
                                    • 1 night min
                                    • Car not necessary
                                    • Air conditioning
                                    • Pet Friendly

                                    Price per night from

                                    $222

                                    Responds fast!
                                    avg. 17 minutes

                                    Price per night from

                                    $222

                                    Distance approx 18.39 km from Highland

                                    (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
                                      …see more

                                      Price per night from

                                      $1,512

                                      Responds fast!
                                      avg. 2 hours 37 minutes

                                      Price per night from

                                      $1,512

                                      Distance approx 11.69 km from Highland

                                        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

                                        $974

                                        Price per night from

                                        $974

                                        Distance approx 14.55 km from Highland

                                        (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 9.41 km from Highland

                                          (1) Excellent 

                                            24

                                            Hudson Valley Home w/Mtn View & Fresh Interior

                                            New York / Ulster Park

                                            Ulster Park house

                                            3 8 min stay varies

                                            • 3 bedrooms
                                            • sleeps 8
                                            • min stay varies
                                            • Ski
                                            • Child Friendly
                                            • Air conditioning

                                            Price per night from

                                            $229

                                            Responds fast!
                                            avg. 36 minutes

                                            Price per night from

                                            $229

                                            Distance approx 12.43 km from Highland

                                              22

                                              Woodland House - sleeps 10 in luxury

                                              New York / Rhinebeck

                                              Rhinebeck house

                                              5 10 2 nights min

                                              • 5 bedrooms
                                              • sleeps 10
                                              • 2 nights min
                                              • Swimming pool
                                              • Child Friendly
                                              • Air conditioning

                                              Price per night from

                                              $684

                                              Price per night from

                                              $684

                                              Distance approx 18.62 km from Highland

                                              (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
                                                …see more

                                                Price per night from

                                                $441

                                                Price per night from

                                                $441

                                                Distance approx 5.02 km from Highland Show on Map

                                                  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

                                                  Distance approx 15.94 km from Highland

                                                    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 13.65 km from Highland

                                                    (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 15.92 km from Highland

                                                      (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

                                                        $287

                                                        Price per night from

                                                        $287

                                                        Distance approx 14.64 km from Highland

                                                          16

                                                          Kingston/Hurley woodland house

                                                          New York / Hurley

                                                          Hurley lodge

                                                          1 4 2 nights min

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

                                                          Price per night from

                                                          $201

                                                          Price per night from

                                                          $201

                                                          Distance approx 14.74 km from Highland

                                                          (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

                                                            $206

                                                            Price per night from

                                                            $206

                                                            Distance approx 15.83 km from Highland

                                                            (4) Excellent 

                                                              6

                                                              Comfy Room in Private Home, Ideal Location, Sauna!

                                                              New York / Kingston

                                                              Kingston room

                                                              1 2 1 night min

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

                                                              Price per night from

                                                              $69

                                                              Responds fast!
                                                              avg. 2 hours 3 minutes

                                                              Price per night from

                                                              $69

                                                              Distance approx 14.63 km from Highland

                                                                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 7.81 km from Highland Show on Map

                                                                  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

                                                                  $352

                                                                  Price per night from

                                                                  $352

                                                                  Distance approx 9.38 km from Highland

                                                                    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. 36 minutes

                                                                    Price per night from

                                                                    $321

                                                                    Distance approx 11.38 km from Highland

                                                                      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

                                                                      $114

                                                                      Price per night from

                                                                      $114

                                                                      Distance approx 7.62 km from Highland Show on Map

                                                                        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. 36 minutes

                                                                        Price per night from

                                                                        $212

                                                                        Distance approx 19.28 km from Highland

                                                                          49

                                                                          Brand New European Style Home+Sauna,Olivebridge NY

                                                                          New York / Olivebridge

                                                                          Olivebridge house

                                                                          3 6 min stay varies

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

                                                                          Price per night from

                                                                          $364

                                                                          Price per night from

                                                                          $364

                                                                          Distance approx 8.86 km from Highland Show on Map

                                                                            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

                                                                            $514

                                                                            Price per night from

                                                                            $514

                                                                            Distance approx 8.93 km from Highland

                                                                            (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

                                                                              $172

                                                                              Price per night from

                                                                              $172