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156 Houses

(1) Excellent 

    18

    Hillhouse Log Cabin

    New York / Hillsdale

    Hillsdale log cabin

    3 13 2 nights min

    • 3 bedrooms
    • sleeps 13
    • 2 nights min
    • Beach / lakeside relaxation
    • Child Friendly
    • Air conditioning
    “rest,relax,recharge” It's a Beautiful home that has all the modern conveniences. It's quiet, quaint and had just what I needed to get away from it all. I enjoyed morning coffee on the back deck among the trees and afternoon walks in the woods. A perfe

    Price per night from

    $487

    Price per night from

    $487

    (17) Excellent 

      31

      Beautifully decorated & immaculate log chalet

      New York / Hillsdale

      Hillsdale log cabin

      3 6 2 nights min

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

      Price per night from

      $201

      Price per night from

      $201

        48

        Total Privacy! Tanglewood Retreat With Berkshire Views!

        New York / Hillsdale

        Hillsdale house

        5 14 2 nights min

        • 5 bedrooms
        • sleeps 14
        • 2 nights min
        • Ask about children

        Price per night from

        $687

        Price per night from

        $687

        (3) Excellent 

          11

          Overnight at Althouse -Higgins

          New York / Hillsdale

          Hillsdale apartment

          2 4 2 nights min

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

          Price per night from

          $201

          Price per night from

          $201

          Great rentals within 20 miles that match your search

          Distance approx 16.24 km from Hillsdale

          (1) Excellent 

            2

            chestnut lodge Queens Room

            Berkshires / Lee

            Lee b and b

            1 2 2 nights min

            • 1 bedroom
            • sleeps 2
            • 2 nights min
            • Ask about pets

            Price per night from

            $165

            Responds fast!
            avg. 36 minutes

            Price per night from

            $165

            Distance approx 13.67 km from Hillsdale

              8

              mile hill b and b

              New York / Kinderhook

              Kinderhook house

              2 4 1 night min

              • 2 bedrooms
              • sleeps 4
              • 1 night min
              • Swimming pool
              • Child Friendly
              • Air conditioning

              Price per night from

              $211

              Price per night from

              $211

              Distance approx 7.61 km from Hillsdale

              (1) Very Good 

                4

                Cozy Copake Lake Cottage

                New York / Copake

                Copake house

                3 6 7 nights min

                • 3 bedrooms
                • sleeps 6
                • 7 nights min
                • Beach / lakeside relaxation
                • Child Friendly
                • Ask about pets

                Price per night from

                $122

                Price per night from

                $122

                Distance approx 7.63 km from Hillsdale

                (8) Excellent 

                  17

                  Outdoor getaway hunting,fishing,skiing..relaxation

                  New York / Copake

                  Copake house

                  3 9 2 nights min

                  • 3 bedrooms
                  • sleeps 9
                  • 2 nights min
                  • Beach / lakeside relaxation
                  • Nearest beach 8 mi
                  • Child Friendly
                  “Home Away from Home ~ A great place to gather11” Had family coming from New York, Massachusetts and Connecticut to celebrate my birthday ~ hotels, motels are expensive, and they're not home. This house offered a great place to convene ~ outdoor gas gr

                  Price per night from

                  $217

                  Price per night from

                  $217

                  Distance approx 4.28 km from Hillsdale Show on Map

                    29

                    Beauty in the Berkshires

                    New York / Austerlitz

                    Austerlitz house

                    6 14 2 nights min

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

                    Price per night from

                    $1,369

                    Price per night from

                    $1,369

                    Distance approx 19.24 km from Hillsdale

                      10

                      Red Mapple Farm

                      New York / Malden Bridge

                      Malden Bridge house

                      4 8 4 nights min

                      • 4 bedrooms
                      • sleeps 8
                      • 4 nights min
                      • Ski
                      • Child Friendly

                      Price per night from

                      $502

                      Price per night from

                      $502

                      Distance approx 15.4 km from Hillsdale

                        23

                        Spacious Lakeside Berkshire Home

                        Berkshires / Monterey

                        Monterey house

                        4 10 3 nights min

                        • 4 bedrooms
                        • sleeps 10
                        • 3 nights min
                        • Child Friendly
                        • Air conditioning
                        • Private garden

                        Price per night from

                        $457

                        Price per night from

                        $457

                        Distance approx 14.82 km from Hillsdale

                        (1) Excellent 

                          9

                          The Artist's House - Special Winter Rates!

                          New York / Hudson

                          Hudson house

                          3 6 2 nights min

                          • 3 bedrooms
                          • sleeps 6
                          • 2 nights min
                          • Car not necessary
                          • Air conditioning
                          • Private garden

                          Price per night from

                          $400

                          Price per night from

                          $400

                          Distance approx 16.24 km from Hillsdale

                            7

                            the BIG room at chestnut lodge

                            Berkshires / Lee

                            Lee b and b

                            1 6 2 nights min

                            • 1 bedroom
                            • sleeps 6
                            • 2 nights min
                            • Ask about children
                            • Pet Friendly

                            Price per night from

                            $229

                            Responds fast!
                            avg. 36 minutes

                            Price per night from

                            $229

                            Distance approx 14.5 km from Hillsdale

                              17

                              Federal house on Armory Square

                              New York / Hudson

                              Hudson house

                              3 8 3 nights min

                              • 3 bedrooms
                              • sleeps 8
                              • 3 nights min
                              • Child Friendly
                              • Air conditioning
                              • Pet Friendly

                              Price per night from

                              $628

                              Price per night from

                              $628

                              Distance approx 19.3 km from Hillsdale

                              (1) Excellent 

                                13

                                Lake House

                                Connecticut / Lakeville

                                Lakeville house

                                5 9 2 nights min

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

                                Price per night from

                                $685

                                Price per night from

                                $685

                                Distance approx 12.04 km from Hillsdale

                                  20

                                  New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)

                                  Berkshires / Richmond

                                  Richmond house

                                  3 6 7 nights min

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

                                  Price per night from

                                  $571

                                  Price per night from

                                  $571

                                  Distance approx 11.26 km from Hillsdale

                                    5

                                    Cozy Modern Condo for the Berkshires

                                    Berkshires / West Stockbridge

                                    West Stockbridge condo

                                    2 6 1 night min

                                    • 2 bedrooms
                                    • sleeps 6
                                    • 1 night min
                                    • Child Friendly
                                    • Air conditioning
                                    • Pet Friendly

                                    Price per night from

                                    $286

                                    Responds fast!
                                    avg. 1 hour 29 minutes

                                    Price per night from

                                    $286

                                    Distance approx 18.47 km from Hillsdale

                                    (3) Excellent 

                                      42

                                      4 Bedroom Furnished House in Lakeville Connecticut

                                      Connecticut / Lakeville

                                      Lakeville house

                                      4 8 2 nights min

                                      • 4 bedrooms
                                      • sleeps 8
                                      • 2 nights min
                                      • Child Friendly
                                      • Air conditioning
                                      • Ask about pets

                                      Price per night from

                                      $371

                                      Price per night from

                                      $371

                                      Distance approx 7.33 km from Hillsdale

                                      (4) Excellent 

                                        30

                                        Gem of the Berkshires, walk to downtown & lake.

                                        Berkshires / Great Barrington

                                        Great Barrington house

                                        5 12 2 nights min

                                        • 5 bedrooms
                                        • sleeps 12
                                        • 2 nights min
                                        • Nearest beach 0.32 mi
                                        • Child Friendly
                                        • Air conditioning
                                        “Wonderful Home!” We had a wonderful weekend! The home and area are lovely - easy walk to town for drinks and dinner - and enjoyed sitting on the many porches, looking out at the view. The home has been upgraded and the kitchen and living areas are b

                                        Price per night from

                                        $343

                                        Price per night from

                                        $343

                                        Distance approx 6.5 km from Hillsdale Show on Map

                                        (1) Excellent 

                                          24

                                          'Butterfly Hill' West Stockbridge Home on 3 Acres!

                                          Berkshires / West Stockbridge

                                          West Stockbridge house

                                          2 4 min stay varies

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

                                          Price per night from

                                          $189

                                          Responds fast!
                                          avg. 40 minutes

                                          Price per night from

                                          $189

                                          Distance approx 14.3 km from Hillsdale

                                            24

                                            3BR Lee House w/ Easy Access to Main Street!

                                            Berkshires / Lee

                                            Lee house

                                            3 10 min stay varies

                                            • 3 bedrooms
                                            • sleeps 10
                                            • min stay varies
                                            • Ski
                                            • Child Friendly

                                            Price per night from

                                            $275

                                            Responds fast!
                                            avg. 40 minutes

                                            Price per night from

                                            $275

                                            Distance approx 3.57 km from Hillsdale Show on Map

                                              32

                                              RIVERSONG "PENTHOUSE"

                                              Berkshires / North Egremont

                                              North Egremont room

                                              1 2 1 night min

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

                                              Price per night from

                                              $172

                                              Responds fast!
                                              avg. 23 minutes

                                              Price per night from

                                              $172

                                              Distance approx 14.36 km from Hillsdale

                                                18

                                                Beautiful House in Downtown Hudson, NY

                                                New York / Hudson

                                                Hudson house

                                                6 10 3 nights min

                                                • 6 bedrooms
                                                • sleeps 10
                                                • 3 nights min
                                                • Nearest beach 201 mi
                                                • Child Friendly
                                                • Car not necessary

                                                Price per night from

                                                $801

                                                Price per night from

                                                $801

                                                Distance approx 10.82 km from Hillsdale

                                                (7) Excellent 

                                                  18

                                                  To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.

                                                  Berkshires / West Stockbridge

                                                  West Stockbridge house

                                                  3 8 min stay varies

                                                  • 3 bedrooms
                                                  • sleeps 8
                                                  • min stay varies
                                                  • Beach / lakeside relaxation
                                                  • Child Friendly
                                                  • Pet Friendly
                                                  “A memorable weekend getaway includes the most perfect house..” My husband and I had the pleasure to rent out this house last summer with another married couple and their son. Although our daughter and their son truly enjoyed Tanglewood and our visits

                                                  Price per night from

                                                  $377

                                                  Price per night from

                                                  $377

                                                  Distance approx 19.77 km from Hillsdale

                                                    19

                                                    The Owls Nest Cabin

                                                    New York / West Coxsackie

                                                    West Coxsackie log cabin

                                                    1 2 2 nights min

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

                                                    Price per night from

                                                    $223

                                                    Price per night from

                                                    $223

                                                    Distance approx 19.77 km from Hillsdale

                                                      13

                                                      Modern cabin in the woods + year round heated pool

                                                      New York / Red Hook

                                                      Red Hook house

                                                      3 7 3 nights min

                                                      • 3 bedrooms
                                                      • sleeps 7
                                                      • 3 nights min
                                                      • Swimming pool
                                                      • Child Friendly
                                                      • Pet Friendly

                                                      Price per night from

                                                      $275

                                                      Price per night from

                                                      $275

                                                      Distance approx 11.47 km from Hillsdale

                                                      (2) Excellent 

                                                        8

                                                        Cozy & Modern Home -mins from Tanglewood & Kripalu

                                                        Berkshires / West Stockbridge

                                                        West Stockbridge apartment

                                                        2 6 1 night min

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • 1 night min
                                                        • Ask about children
                                                        • Air conditioning
                                                        • Ask about pets

                                                        Price per night from

                                                        $115

                                                        Responds fast!
                                                        avg. 1 hour 29 minutes

                                                        Price per night from

                                                        $115

                                                        Distance approx 14.01 km from Hillsdale

                                                          19

                                                          Berkshire Country Estate - Rose Suite

                                                          New York / Old Chatham

                                                          Old Chatham villa

                                                          2 4 2 nights min

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

                                                          Price per night from

                                                          $195

                                                          Price per night from

                                                          $195

                                                          Distance approx 15.14 km from Hillsdale

                                                          (2) Very Good 

                                                            12

                                                            Berkshires Spacious Comfortable Charming Farmhouse

                                                            Berkshires / Lee

                                                            Lee apartment

                                                            3 8 2 nights min

                                                            • 3 bedrooms
                                                            • sleeps 8
                                                            • 2 nights min
                                                            • Child Friendly
                                                            • Air conditioning
                                                            “lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.

                                                            Price per night from

                                                            $343

                                                            Price per night from

                                                            $343

                                                            Distance approx 11.86 km from Hillsdale

                                                              12

                                                              Fabulous Post & Beam Berkshire Rental

                                                              Berkshires / Monterey

                                                              Monterey house

                                                              7 21 nights min

                                                              • sleeps 7
                                                              • 21 nights min
                                                              • Ask about children
                                                              • Car not necessary
                                                              • Ask about pets

                                                              Price per night from

                                                              $205

                                                              Price per night from

                                                              $205

                                                              Distance approx 14.16 km from Hillsdale

                                                                13

                                                                Garfield House

                                                                Maine / Lee

                                                                Lee apartment

                                                                2 6 2 nights min

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

                                                                Price per night from

                                                                $201

                                                                Price per night from

                                                                $201

                                                                Distance approx 17.66 km from Hillsdale

                                                                  19

                                                                  Brook Hill Farm House

                                                                  New York / Valatie

                                                                  Valatie house

                                                                  4 12 3 nights min

                                                                  • 4 bedrooms
                                                                  • sleeps 12
                                                                  • 3 nights min
                                                                  • Child Friendly
                                                                  • Pet Friendly

                                                                  Price per night from

                                                                  $377

                                                                  Price per night from

                                                                  $377

                                                                  Distance approx 15.9 km from Hillsdale

                                                                    23

                                                                    Bassinova-on-Hudson

                                                                    New York / Coxsackie

                                                                    Coxsackie villa

                                                                    5 10 2 nights min

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

                                                                    Price per night from

                                                                    $2,859

                                                                    Price per night from

                                                                    $2,859

                                                                    Distance approx 14.01 km from Hillsdale

                                                                    (1) Excellent 

                                                                      21

                                                                      Berkshire Country Estate - The Library Suite

                                                                      New York / Old Chatham

                                                                      Old Chatham house

                                                                      2 4 2 nights min

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

                                                                      Price per night from

                                                                      $172

                                                                      Price per night from

                                                                      $172

                                                                      Distance approx 10.61 km from Hillsdale

                                                                        16

                                                                        Olde York Farm Distillery Suite

                                                                        New York / Claverack

                                                                        Claverack farmhouse

                                                                        2 6 1 night min

                                                                        • 2 bedrooms
                                                                        • sleeps 6
                                                                        • 1 night min
                                                                        • Beach / lakeside relaxation
                                                                        • Child Friendly
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $286

                                                                        Price per night from

                                                                        $286

                                                                        Distance approx 15.98 km from Hillsdale

                                                                          31

                                                                          Lakefront house , great lake and mountain views

                                                                          Catskill Region / Athens

                                                                          Athens house

                                                                          4 10 3 nights min

                                                                          • 4 bedrooms
                                                                          • sleeps 10
                                                                          • 3 nights min
                                                                          • Beach / lakeside relaxation
                                                                          • Swimming pool
                                                                          • Child Friendly

                                                                          Price per night from

                                                                          $358

                                                                          Price per night from

                                                                          $358

                                                                          Distance approx 14.32 km from Hillsdale

                                                                          (1) Excellent 

                                                                            10

                                                                            Berkshire House Share-The Blue Room

                                                                            Berkshires / Lee

                                                                            Lee house

                                                                            3 2 1 night min

                                                                            • 3 bedrooms
                                                                            • sleeps 2
                                                                            • 1 night min

                                                                            Price per night from

                                                                            $86

                                                                            Price per night from

                                                                            $86

                                                                            Distance approx 8.97 km from Hillsdale

                                                                            (39) Excellent 

                                                                              20

                                                                              Berkshire Farmhouse Vacation

                                                                              Berkshires / West Stockbridge

                                                                              West Stockbridge house

                                                                              5 12 min stay varies

                                                                              • 5 bedrooms
                                                                              • sleeps 12
                                                                              • min stay varies
                                                                              • Nearest beach 2 mi
                                                                              • Child Friendly
                                                                              • Pet Friendly
                                                                              “Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the l

                                                                              Price per night from

                                                                              $298

                                                                              Price per night from

                                                                              $298