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Filtering by: Water sports

26 Houses

    32

    Berkshire Home on Lake Garfield w/Dock & Boats

    Berkshires / Monterey

    Monterey house

    4 12 min stay varies

    • 4 bedrooms
    • sleeps 12
    • min stay varies
    • Ski
    • Child Friendly
    • Air conditioning

    Price per night from

    $344

    Responds fast!
    avg. 21 minutes

    Price per night from

    $344

      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

        24

        NEW-Pet-Friendly Berkshires Home w/Dock & Fire Pit

        Berkshires / Monterey

        Monterey house

        3 10 7 nights min

        • 3 bedrooms
        • sleeps 10
        • 7 nights min
        • Child Friendly
        • Pet Friendly

        Price per night from

        $212

        Responds fast!
        avg. 21 minutes

        Price per night from

        $212

        Great rentals within 20 miles that match your search

        Distance approx 4.59 km from Monterey Show on Map

          17

          Picturesque 19th century home on 3 private acres

          Berkshires / New Marlborough

          New Marlborough house

          4 7 min stay varies

          • 4 bedrooms
          • sleeps 7
          • min stay varies
          • Child Friendly
          • Private garden

          Price per night from

          $171

          Price per night from

          $171

          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 10.09 km from Monterey

                31

                |The Escape |STOCKBRIDGE| NEW Home |BERKSHIRES|

                Berkshires / Stockbridge

                Stockbridge house

                4 9 min stay varies

                • 4 bedrooms
                • sleeps 9
                • min stay varies
                • Child Friendly
                • Air conditioning
                • Pet Friendly

                Price per night from

                $514

                Responds fast!
                avg. 1 hour 21 minutes

                Price per night from

                $514

                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 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

                    $326

                    Price per night from

                    $326

                    Distance approx 9.81 km from Monterey

                      16

                      Beautifully Renovated Berkshires Farmhouse

                      Berkshires / West Stockbridge

                      West Stockbridge b&b

                      2 4 2 nights min

                      • 2 bedrooms
                      • sleeps 4
                      • 2 nights min
                      • Air conditioning
                      • Private garden

                      Price per night from

                      $240

                      Price per night from

                      $240

                      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 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

                          $452

                          Responds fast!
                          avg. 1 hour 37 minutes

                          Price per night from

                          $452

                          Distance approx 9.46 km from Monterey

                            6

                            Stunning Home! 120 Acres! Amazing!

                            Berkshires / Great Barrington

                            Great Barrington house

                            9 16 3 nights min

                            • 9 bedrooms
                            • sleeps 16
                            • 3 nights min
                            • Swimming pool
                            • Child Friendly
                            • Air conditioning

                            Price per night from

                            $4,113

                            Price per night from

                            $4,113

                            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 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

                                $816

                                Price per night from

                                $816

                                Distance approx 7.73 km from Monterey

                                  4

                                  Just the Spot! Cozy home by the Lake...

                                  Berkshires / Great Barrington

                                  Great Barrington house

                                  3 7 2 nights min

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

                                  Price per night from

                                  $201

                                  Price per night from

                                  $201

                                  Distance approx 8.76 km from Monterey

                                    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. 21 minutes

                                    Price per night from

                                    $275

                                    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 8.5 km from Monterey

                                      (2) Excellent 

                                        22

                                        BSO Tanglewood + Jacob's Pillow. Lenox-Stockbridge. 5bdr/6bth. sleeps 24+

                                        Berkshires / Lee

                                        Lee house

                                        5 30 min stay varies

                                        • 5 bedrooms
                                        • sleeps 30
                                        • min stay varies
                                        • Nearest beach 3 mi
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $915

                                        Responds fast!
                                        avg. 1 hour 36 minutes

                                        Price per night from

                                        $915

                                        Distance approx 8.24 km from Monterey

                                          30

                                          NEW! Becket Home on 11 Acres w/ Swimming Pond!

                                          Berkshires / Becket

                                          Becket house

                                          3 8 min stay varies

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

                                          Price per night from

                                          $373

                                          Responds fast!
                                          avg. 21 minutes

                                          Price per night from

                                          $373

                                          Distance approx 8.62 km from Monterey

                                          (5) Excellent 

                                            10

                                            Apple Cottage

                                            Berkshires / Sheffield

                                            Sheffield farmhouse

                                            3 8 1 night min

                                            • 3 bedrooms
                                            • sleeps 8
                                            • 1 night min
                                            • Ask about children
                                            • Air conditioning
                                            • Private garden

                                            Price per night from

                                            $430

                                            Responds fast!
                                            avg. 3 hours 22 minutes

                                            Price per night from

                                            $430

                                            Distance approx 11.19 km from Monterey

                                              19

                                              One of the Finest Homes and Best location in the Berkshires

                                              Berkshires / Stockbridge

                                              Stockbridge house

                                              4 10 2 nights min

                                              • 4 bedrooms
                                              • sleeps 10
                                              • 2 nights min
                                              • Child Friendly
                                              • Air conditioning
                                              • Pet Friendly

                                              Price per night from

                                              $802

                                              Price per night from

                                              $802

                                              Distance approx 3.49 km from Monterey Show on Map

                                              (4) Excellent 

                                                24

                                                Waterfront Cottage - 10 Mins to Great Barrington!

                                                Berkshires / New Marlborough

                                                New Marlborough cottage

                                                2 4 min stay varies

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

                                                Price per night from

                                                $206

                                                Responds fast!
                                                avg. 21 minutes

                                                Price per night from

                                                $206

                                                Distance approx 16.07 km from Monterey

                                                (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

                                                  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 8.76 km from Monterey

                                                      26

                                                      3BD Newly Rennovated Contempoary Near Stockbridge

                                                      Berkshires / Stockbridge

                                                      Stockbridge house

                                                      3 6 3 nights min

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

                                                      Price per night from

                                                      $344

                                                      Price per night from

                                                      $344