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20 Houses

    24

    Beautiful Lakefront Berkshire Rental

    Berkshires / Monterey

    Monterey house

    5 6 7 nights min

    • 5 bedrooms
    • sleeps 6
    • 7 nights min
    • Beach / lakeside relaxation
    • Child Friendly
    • Air conditioning

    Price per night from

    $489

    Price per night from

    $489

    Great rentals within 20 miles that match your search

    Distance approx 11.74 km from Monterey

    (14) Excellent 

    Certificate of Excellence

      55

      RiverSong Suite In The Berkshires

      Berkshires / North Egremont

      North Egremont apartment

      1 2 1 night min

      • 1 bedroom
      • sleeps 2
      • 1 night min
      • Beach / lakeside relaxation
      • Nearest beach 2 mi
      • Air conditioning

      Certificate of Excellence

      Price per night from

      $215

      Responds fast!
      avg. 11 minutes

      Price per night from

      $215

      Distance approx 12.84 km from Monterey

      (4) Excellent 

        10

        Comfortable Farmhouse in the Berkshires

        Berkshires / West Stockbridge

        West Stockbridge farmhouse

        5 12 2 nights min

        • 5 bedrooms
        • sleeps 12
        • 2 nights min
        • Beach / lakeside relaxation
        • Child Friendly
        • Air conditioning

        Price per night from

        $371

        Responds fast!
        avg. 3 hours 37 minutes

        Price per night from

        $371

        Distance approx 18.08 km from Monterey

        (2) Excellent 

          14

          Newly Renovated Lakefront Getaway on Robinson Pond

          New York / Copake

          Copake house

          3 5 3 nights min

          • 3 bedrooms
          • sleeps 5
          • 3 nights min
          • Beach / lakeside relaxation
          • Nearest beach 0 mi
          • Child Friendly

          Price per night from

          $229

          Responds fast!
          avg. 1 hour 58 minutes

          Price per night from

          $229

          Distance approx 10.19 km from Monterey

          (4) Very Good 

            18

            Lakefront Berkshires Ski/Summer House, Great Views

            Berkshires / Great Barrington

            Great Barrington house

            4 10 min stay varies

            • 4 bedrooms
            • sleeps 10
            • min stay varies
            • Beach / lakeside relaxation
            • Child Friendly
            • Pet Friendly

            Price per night from

            $215

            Price per night from

            $215

            Distance approx 13.88 km from Monterey

            (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

              $486

              Price per night from

              $486

              Distance approx 16.81 km from Monterey

              (4) Excellent 

                10

                Great Vacation House in the Berkshires by Richmond Pond

                Berkshires / Richmond

                Richmond house

                2 6 min stay varies

                • 2 bedrooms
                • sleeps 6
                • min stay varies
                • Beach / lakeside relaxation
                • Child Friendly
                • Air conditioning

                Price per night from

                $213

                Price per night from

                $213

                Distance approx 14.02 km from Monterey

                (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

                  $376

                  Price per night from

                  $376

                  Distance approx 18.3 km from Monterey

                    9

                    Cedar Chest

                    New York / Canaan

                    Canaan cottage

                    1 2 7 nights min

                    • 1 bedroom
                    • sleeps 2
                    • 7 nights min
                    • Beach / lakeside relaxation
                    • Nearest beach 2 mi
                    • Air conditioning

                    Price per night from

                    $115

                    Price per night from

                    $115

                    Distance approx 9.75 km from Monterey

                    (1) Excellent 

                      20

                      Newly Renovated Colonial on the River! Sleeps 5-6

                      Berkshires / Stockbridge

                      Stockbridge house

                      3 5 3 nights min

                      • 3 bedrooms
                      • sleeps 5
                      • 3 nights min
                      • Beach / lakeside relaxation
                      • Child Friendly

                      Price per night from

                      $327

                      Price per night from

                      $327

                      Distance approx 9.1 km from Monterey

                        18

                        Spacious wooded home

                        Berkshires / Becket

                        Becket house

                        4 12 3 nights min

                        • 4 bedrooms
                        • sleeps 12
                        • 3 nights min
                        • Beach / lakeside relaxation
                        • Private garden

                        Price per night from

                        $224

                        Price per night from

                        $224

                        Distance approx 19.35 km from Monterey

                          14

                          Modern Cozy Wooded Retreat

                          New York / Spencertown

                          Spencertown house

                          2 6 30 nights min

                          • 2 bedrooms
                          • sleeps 6
                          • 30 nights min
                          • Beach / lakeside relaxation
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $153

                          Price per night from

                          $153

                          Distance approx 13.79 km from Monterey

                          (1) Excellent 

                            37

                            Charming 2+2 Lakeside Cottage on Best Lake in CT

                            Connecticut / Salisbury

                            Salisbury cottage

                            2 4 30 nights min

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

                            Price per night from

                            $206

                            Price per night from

                            $206

                            Distance approx 8.62 km from Monterey

                            (1) Excellent 

                              20

                              Enjoy horses and the largest recreational lake in Massachusetts

                              Berkshires / East Otis

                              East Otis apartment

                              1 4 1 night min

                              • 1 bedroom
                              • sleeps 4
                              • 1 night min
                              • Beach / lakeside relaxation
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $126

                              Responds fast!
                              avg. 2 hours 32 minutes

                              Price per night from

                              $126

                              Distance approx 8.59 km from Monterey

                              (5) Excellent 

                                32

                                Beautiful Vacation Home

                                Berkshires / Stockbridge

                                Stockbridge house

                                4 12 min stay varies

                                • 4 bedrooms
                                • sleeps 12
                                • min stay varies
                                • Beach / lakeside relaxation
                                • Child Friendly
                                • Car not necessary

                                Price per night from

                                $572

                                Price per night from

                                $572

                                Distance approx 5.16 km from Monterey

                                (1) Average 

                                  15

                                  Charming and Spacious Colonial Farmhouse on 4 Acre Estate

                                  Berkshires / Tyringham

                                  Tyringham villa

                                  4 8 2 nights min

                                  • 4 bedrooms
                                  • sleeps 8
                                  • 2 nights min
                                  • Beach / lakeside relaxation
                                  • Nearest beach 2 mi
                                  • Child Friendly

                                  Price per night from

                                  $453

                                  Responds fast!
                                  avg. 1 hour 37 minutes

                                  Price per night from

                                  $453

                                  Distance approx 11.4 km from Monterey

                                  (6) Excellent 

                                    16

                                    Family-friendly Cottage Near Lake, Tanglewood

                                    Berkshires / Stockbridge

                                    Stockbridge cottage

                                    3 7 2 nights min

                                    • 3 bedrooms
                                    • sleeps 7
                                    • 2 nights min
                                    • Beach / lakeside relaxation
                                    • Nearest beach 0.2 mi
                                    • Child Friendly

                                    Price per night from

                                    $327

                                    Price per night from

                                    $327

                                    Distance approx 18.14 km from Monterey

                                    (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

                                      $218

                                      Price per night from

                                      $218

                                      Distance approx 9.28 km from Monterey

                                        15

                                        House share/room for rent

                                        Berkshires / Lee

                                        Lee private room

                                        1 1 1 night min

                                        • 1 bedroom
                                        • sleeps 1
                                        • 1 night min
                                        • Beach / lakeside relaxation
                                        • Nearest beach 3 mi

                                        Price per night from

                                        $77

                                        Price per night from

                                        $77

                                        Distance approx 10.2 km from Monterey

                                        (4) Excellent 

                                          18

                                          Lake House

                                          Berkshires / Lee

                                          Lee house

                                          5 9 7 nights min

                                          • 5 bedrooms
                                          • sleeps 9
                                          • 7 nights min
                                          • Beach / lakeside relaxation
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $818

                                          Price per night from

                                          $818