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238 Houses

    32

    mid century modern ranch woodstock pool

    New York / Bearsville

    Bearsville house

    3 6 2 nights min

    • 3 bedrooms
    • sleeps 6
    • 2 nights min
    • Beach / lakeside relaxation
    • Swimming pool
    • Child Friendly

    Price per night from

    $516

    Price per night from

    $516

    (1) Excellent 

      29

      Woodstock Modern House with Pool and Hot Tub

      New York / Bearsville

      Bearsville house

      4 8 2 nights min

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

      Price per night from

      $516

      Price per night from

      $516

        24

        NEW! Bearsville Cabin - Pet Friendly - Near Hikes!

        New York / Bearsville

        Bearsville cottage

        2 4 min stay varies

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

        Price per night from

        $178

        Responds fast!
        avg. 11 minutes

        Price per night from

        $178

        Great rentals within 20 miles that match your search

        Distance approx 15.63 km from Bearsville

          24

          Two-Story, 3-Bedroom Family Home

          Catskill Region / Windham

          Windham house

          3 4 2 nights min

          • 3 bedrooms
          • sleeps 4
          • 2 nights min
          • Child Friendly
          • Private garden

          Price per night from

          $229

          Price per night from

          $229

          Distance approx 10.5 km from Bearsville

            7

            Hunter Mountain Ski House Condo Ski Season Rental

            Catskill Region / Hunter

            Hunter apartment

            1 6 3 nights min

            • 1 bedroom
            • sleeps 6
            • 3 nights min
            • Nearest beach 1 mi
            • Swimming pool
            • Child Friendly

            Price per night from

            $115

            Price per night from

            $115

            Distance approx 19.15 km from Bearsville

              7

              Secluded House in the Woods w/ Year Round Hot Tub

              New York / Red Hook

              Red Hook house

              2 4 3 nights min

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

              Price per night from

              $229

              Price per night from

              $229

              Distance approx 9.71 km from Bearsville

                19

                1894 Catskills Farmhouse Retreat

                Catskill Region / Hunter

                Hunter house

                4 8 2 nights min

                • 4 bedrooms
                • sleeps 8
                • 2 nights min
                • Child Friendly
                • Pet Friendly

                Price per night from

                $361

                Price per night from

                $361

                Distance approx 11.06 km from Bearsville

                (1) Excellent 

                  16

                  Charming Star Sapphire Cabin with Luxury Hot Tub near Windham & Hunter Mtn.

                  Catskill Region / Hunter

                  Hunter house

                  3 2 1 night min

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

                  Price per night from

                  $401

                  Price per night from

                  $401

                  Distance approx 18.39 km from Bearsville

                  (1) Excellent 

                    34

                    Magnificent Catskill Mountaintop Home!

                    Catskill Region / West Kill

                    West Kill chateau

                    7 14 2 nights min

                    • 7 bedrooms
                    • sleeps 14
                    • 2 nights min
                    • Child Friendly

                    Price per night from

                    $1,718

                    Price per night from

                    $1,718

                    Distance approx 10.73 km from Bearsville

                    (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 3.86 km from Bearsville Show on Map

                        27

                        Zen Mt. Tremper Home w/Incredible Views & Hot Tub!

                        New York / Mount Tremper

                        Mount Tremper house

                        3 6 min stay varies

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

                        Price per night from

                        $315

                        Responds fast!
                        avg. 29 minutes

                        Price per night from

                        $315

                        Distance approx 9.47 km from Bearsville Show on Map

                        (5) Excellent 

                          42

                          Woodland Valley Retreat-beautiful mountain cottage

                          Catskill Region / Phoenicia

                          Phoenicia house

                          2 5 4 nights min

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

                          Price per night from

                          $155

                          Responds fast!
                          avg. 2 hours 29 minutes

                          Price per night from

                          $155

                          Distance approx 18.09 km from Bearsville

                          (1) Excellent 

                            26

                            ***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***

                            Catskill Region / Windham

                            Windham house

                            2 5 2 nights min

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

                            Price per night from

                            $201

                            Responds fast!
                            avg. 2 hours 2 minutes

                            Price per night from

                            $201

                            Distance approx 16.6 km from Bearsville

                            (3) Average 

                              5

                              Windham Cabin

                              New York / Lexington

                              Lexington log cabin

                              3 6 2 nights min

                              • 3 bedrooms
                              • sleeps 6
                              • 2 nights min
                              • Nearest beach 24 mi
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $172

                              Price per night from

                              $172

                              Distance approx 18.4 km from Bearsville

                                31

                                NEW! Sleek 4BR Windham House w/Hot Tub & Mtn Views

                                Catskill Region / Windham

                                Windham house

                                4 10 min stay varies

                                • 4 bedrooms
                                • sleeps 10
                                • min stay varies
                                • Child Friendly
                                • Ask about pets

                                Price per night from

                                $516

                                Responds fast!
                                avg. 19 minutes

                                Price per night from

                                $516

                                Distance approx 9.32 km from Bearsville

                                (8) Excellent 

                                  27

                                  Saugerties, Woodstock, Catskills, Hunter, HITS, Rental House

                                  Catskill Region / Saugerties

                                  Saugerties house

                                  3 6 min stay varies

                                  • 3 bedrooms
                                  • sleeps 6
                                  • min stay varies
                                  • Nearest beach 6 mi
                                  • Child Friendly
                                  • Air conditioning
                                  “Awesome Columbus Weekend” Myself and 4 friends stayed here for a long Columbus Day weekend. This place is just what we needed. We are all from NYC so the location was extermely convenient for us. The Catskills are just a short drive from the city..
                                  …see more

                                  Price per night from

                                  $195

                                  Responds fast!
                                  avg. 1 hour 0 minutes

                                  Price per night from

                                  $195

                                  Distance approx 11.5 km from Bearsville

                                  (8) Excellent 

                                    11

                                    Expanded Cabin facing Hunter Mountain in NY

                                    Catskill Region / Hunter

                                    Hunter log cabin

                                    4 7 2 nights min

                                    • 4 bedrooms
                                    • sleeps 7
                                    • 2 nights min
                                    • Beach / lakeside relaxation
                                    • Child Friendly
                                    • Car not necessary
                                    “Love it--would return again!” Jeffrey was very friendly, accommodating, helpful and professional as we were booking the cabin. Cabin was beautifully furnished and large enough to fit 8 of us. 5 min drive to Hunter Mountain. Very cozy and comfortabl
                                    …see more

                                    Price per night from

                                    $687

                                    Responds fast!
                                    avg. 2 hours 38 minutes

                                    Price per night from

                                    $687

                                    Distance approx 11.3 km from Bearsville

                                    (7) Excellent 

                                      45

                                      THE LAKE HOUSE AT HUNTER FOUR SEASON FUN!

                                      Catskill Region / Hunter

                                      Hunter chalet

                                      3 8 2 nights min

                                      • 3 bedrooms
                                      • sleeps 8
                                      • 2 nights min
                                      • Beach / lakeside relaxation
                                      • Ski
                                      • Child Friendly

                                      Price per night from

                                      $401

                                      Responds fast!
                                      avg. 2 hours 21 minutes

                                      Price per night from

                                      $401

                                      Distance approx 11.03 km from Bearsville

                                        24

                                        Hunter Home w/Fire Pit- Steps to Schoharie River!

                                        Catskill Region / Hunter

                                        Hunter house

                                        5 12 min stay varies

                                        • 5 bedrooms
                                        • sleeps 12
                                        • min stay varies
                                        • Ski
                                        • Child Friendly
                                        • Pet Friendly

                                        Price per night from

                                        $287

                                        Responds fast!
                                        avg. 35 minutes

                                        Price per night from

                                        $287

                                        Distance approx 3.61 km from Bearsville Show on Map

                                        (5) Excellent 

                                          36

                                          Mid Century Ranch-Hot Tub-Minutes to Center ofTown

                                          Catskill Region / Woodstock

                                          Woodstock house

                                          4 8 3 nights min

                                          • 4 bedrooms
                                          • sleeps 8
                                          • 3 nights min
                                          • Nearest beach 1 mi
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $401

                                          Responds fast!
                                          avg. 2 hours 29 minutes

                                          Price per night from

                                          $401

                                          Distance approx 16.3 km from Bearsville

                                          (2) Excellent 

                                            31

                                            Charming house in great location

                                            New York / Jewett

                                            Jewett house

                                            3 8 2 nights min

                                            • 3 bedrooms
                                            • sleeps 8
                                            • 2 nights min
                                            • Beach / lakeside relaxation
                                            • Air conditioning
                                            • Private garden

                                            Price per night from

                                            $344

                                            Price per night from

                                            $344

                                            Distance approx 1.18 km from Bearsville Show on Map

                                            (6) Excellent 

                                              30

                                              Pet Friendly Cabin Doh-Ray Up At 1450ft

                                              Catskill Region / Woodstock

                                              Woodstock house

                                              2 5 min stay varies

                                              • 2 bedrooms
                                              • sleeps 5
                                              • min stay varies
                                              • Ski
                                              • Child Friendly
                                              • Pet Friendly
                                              “Relaxing mountain retreat” We enjoyed a very pleasant Thanksgiving week getaway at the cabin, which looks just like the pictures -- nice combination of modern and rustic design. Also very comfortable, clean and well organized. Tv and sound system very
                                              …see more

                                              Price per night from

                                              $292

                                              Responds fast!
                                              avg. 2 hours 19 minutes

                                              Price per night from

                                              $292

                                              Distance approx 6.34 km from Bearsville Show on Map

                                                4

                                                Cozy and comfortable

                                                New York / Boiceville

                                                Boiceville apartment

                                                1 4 2 nights min

                                                • 1 bedroom
                                                • sleeps 4
                                                • 2 nights min
                                                • Child Friendly
                                                • Air conditioning
                                                • Pet Friendly

                                                Price per night from

                                                $109

                                                Price per night from

                                                $109

                                                Distance approx 10.83 km from Bearsville

                                                  10

                                                  Cozy Cabin Feel Across from Hunter Mountain

                                                  Catskill Region / Hunter

                                                  Hunter apartment

                                                  2 5 min stay varies

                                                  • 2 bedrooms
                                                  • sleeps 5
                                                  • min stay varies
                                                  • Ski
                                                  • Child Friendly

                                                  Price per night from

                                                  $229

                                                  Responds fast!
                                                  avg. 34 minutes

                                                  Price per night from

                                                  $229

                                                  Distance approx 11.2 km from Bearsville

                                                  (2) Very Good 

                                                    17

                                                    Hunter Mountain House of Hunter

                                                    Catskill Region / Hunter

                                                    Hunter house

                                                    6 12 2 nights min

                                                    • 6 bedrooms
                                                    • sleeps 12
                                                    • 2 nights min
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 16 mi
                                                    • Child Friendly
                                                    “Great Place for our Large Group!” We recently stayed at this house with our large group of 14! There was plenty of room for everyone in this spacious home. We had such a fun time playing pool and enjoying the bar. We especially enjoyed the back deck
                                                    …see more

                                                    Price per night from

                                                    $573

                                                    Responds fast!
                                                    avg. 1 hour 24 minutes

                                                    Price per night from

                                                    $573

                                                    Distance approx 15.34 km from Bearsville

                                                    (4) Very Good 

                                                      18

                                                      Mountain Treasure Cottage, WIndham, NY

                                                      Catskill Region / Windham

                                                      Windham cottage

                                                      2 8 2 nights min

                                                      • 2 bedrooms
                                                      • sleeps 8
                                                      • 2 nights min
                                                      • Child Friendly
                                                      • Car not necessary
                                                      • Air conditioning

                                                      Price per night from

                                                      $286

                                                      Responds fast!
                                                      avg. 2 hours 51 minutes

                                                      Price per night from

                                                      $286

                                                      Distance approx 3.37 km from Bearsville Show on Map

                                                        25

                                                        Sun Salutations in Woodstock, a mile to the village & a stop on Trailways

                                                        Catskill Region / Woodstock

                                                        Woodstock house

                                                        4 8 2 nights min

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

                                                        Price per night from

                                                        $286

                                                        Responds fast!
                                                        avg. 2 hours 8 minutes

                                                        Price per night from

                                                        $286

                                                        Distance approx 17.33 km from Bearsville

                                                        (4) Very Good 

                                                          23

                                                          On A Road Less Traveled -Catskill Mountain Retreat

                                                          New York / Lexington

                                                          Lexington house

                                                          3 10 2 nights min

                                                          • 3 bedrooms
                                                          • sleeps 10
                                                          • 2 nights min
                                                          • Child Friendly
                                                          • Car not necessary
                                                          • Air conditioning
                                                          “Great place to get away” The house very clean inside and had everything we wanted. The outside had a huge deck, as well as a hot tub for extreme relaxation and tranquility. Would definitely go back.
                                                          …see more

                                                          Price per night from

                                                          $247

                                                          Price per night from

                                                          $247

                                                          Distance approx 15.72 km from Bearsville

                                                            17

                                                            Hunter / Windham Catskills Getaway

                                                            New York / Jewett

                                                            Jewett house

                                                            3 7 2 nights min

                                                            • 3 bedrooms
                                                            • sleeps 7
                                                            • 2 nights min
                                                            • Child Friendly
                                                            • Private garden

                                                            Price per night from

                                                            $195

                                                            Price per night from

                                                            $195

                                                            Distance approx 5.86 km from Bearsville Show on Map

                                                              26

                                                              NEW! Rustic Mt Tremper Home w/Patio-Near Woodstock

                                                              New York / Mount Tremper

                                                              Mount Tremper house

                                                              4 8 min stay varies

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

                                                              Price per night from

                                                              $224

                                                              Responds fast!
                                                              avg. 29 minutes

                                                              Price per night from

                                                              $224

                                                              Distance approx 4.14 km from Bearsville Show on Map

                                                              (1) Excellent 

                                                                22

                                                                Woodstock Stone Cottage Swim Lake 3 ski resorts fishing hiking biking music arts

                                                                Catskill Region / Woodstock

                                                                Woodstock house

                                                                4 8 2 nights min

                                                                • 4 bedrooms
                                                                • sleeps 8
                                                                • 2 nights min
                                                                • Beach / lakeside relaxation
                                                                • Ski
                                                                • Child Friendly

                                                                Price per night from

                                                                $453

                                                                Responds fast!
                                                                avg. 2 hours 3 minutes

                                                                Price per night from

                                                                $453

                                                                Distance approx 9.91 km from Bearsville

                                                                  19

                                                                  Beautiful Home on The Esopus Creek

                                                                  Catskill Region / Saugerties

                                                                  Saugerties house

                                                                  1 4 2 nights min

                                                                  • 1 bedroom
                                                                  • sleeps 4
                                                                  • 2 nights min
                                                                  • Nearest beach 5 mi
                                                                  • Air conditioning
                                                                  • Pet Friendly

                                                                  Price per night from

                                                                  $287

                                                                  Price per night from

                                                                  $287

                                                                  Distance approx 17.91 km from Bearsville

                                                                  (14) Excellent 

                                                                    28

                                                                    Tumblin' Falls House

                                                                    Catskill Region / Catskill

                                                                    Catskill house

                                                                    5 12 2 nights min

                                                                    • 5 bedrooms
                                                                    • sleeps 12
                                                                    • 2 nights min
                                                                    • Beach / lakeside relaxation
                                                                    • Ask about children
                                                                    • Air conditioning
                                                                    “Our second home!” Tumblin' Falls has been our home away from home since we first discovered it in the mid-1990s. There's no better place to kick back and enjoy the mountain air, the beautiful waterfall, the company of wonderful people, and the warm fe
                                                                    …see more

                                                                    Price per night from

                                                                    $687

                                                                    Responds fast!
                                                                    avg. 2 hours 7 minutes

                                                                    Price per night from

                                                                    $687

                                                                    Distance approx 13.59 km from Bearsville

                                                                      14

                                                                      JW LODGING- Comfortable Country Home, Ideal for Groups Touring Bethel Complexes!

                                                                      New York / Red Hook

                                                                      Red Hook apartment

                                                                      2 8 4 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 8
                                                                      • 4 nights min
                                                                      • Nearest beach 10 mi
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $172

                                                                      Price per night from

                                                                      $172

                                                                      Distance approx 1.17 km from Bearsville Show on Map

                                                                        20

                                                                        Historic Southwestern Chalet

                                                                        Catskill Region / Woodstock

                                                                        Woodstock house

                                                                        4 12 min stay varies

                                                                        • 4 bedrooms
                                                                        • sleeps 12
                                                                        • min stay varies
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $401

                                                                        Price per night from

                                                                        $401

                                                                        Distance approx 1.05 km from Bearsville Show on Map

                                                                        (3) Average 

                                                                          20

                                                                          2 BR Cabin, Hot Tub, Fireplace, Heart of Woodstock

                                                                          Catskill Region / Woodstock

                                                                          Woodstock log cabin

                                                                          2 6 2 nights min

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

                                                                          Price per night from

                                                                          $258

                                                                          Responds fast!
                                                                          avg. 2 hours 44 minutes

                                                                          Price per night from

                                                                          $258

                                                                          Distance approx 3.64 km from Bearsville Show on Map

                                                                            25

                                                                            Tranquil Retreat Stunning Views+Hot Tub, Woodstock Area -The Glenford House

                                                                            Catskill Region / Glenford

                                                                            Glenford house

                                                                            3 6 min stay varies

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

                                                                            Price per night from

                                                                            $315

                                                                            Price per night from

                                                                            $315

                                                                            Distance approx 17.24 km from Bearsville

                                                                            (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