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27 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

    $490

    Price per night from

    $490

    Great rentals within 20 miles that match your search

    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 13.88 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

        $488

        Price per night from

        $488

        Distance approx 19.18 km from Monterey

          8

          New Timberframe House Rental in the Berkshire Mountains, Masschusetts

          Berkshires / Hinsdale

          Hinsdale house

          3 6 2 nights min

          • 3 bedrooms
          • sleeps 6
          • 2 nights min
          • Child Friendly
          • Ask about pets
          • Private garden

          Price per night from

          $167

          Price per night from

          $167

          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

            $373

            Responds fast!
            avg. 3 hours 37 minutes

            Price per night from

            $373

            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 7.61 km from Monterey

                23

                Newly Renovated Berkshire Cottage near Tanglewood

                Berkshires / Lee

                Lee cottage

                1 2 60 nights min

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

                Price per night from

                $327

                Responds fast!
                avg. 12 minutes

                Price per night from

                $327

                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

                  $172

                  Price per night from

                  $172

                  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 8.5 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

                      $916

                      Responds fast!
                      avg. 1 hour 36 minutes

                      Price per night from

                      $916

                      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 8.6 km from Monterey

                        (1) Excellent 

                          17

                          Restored 1886 Eyebrow Colonial

                          Berkshires / Stockbridge

                          Stockbridge house

                          2 6 7 nights min

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

                          Price per night from

                          $246

                          Price per night from

                          $246

                          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

                            $216

                            Price per night from

                            $216

                            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

                              $217

                              Responds fast!
                              avg. 11 minutes

                              Price per night from

                              $217

                              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 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 9.81 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

                                    $241

                                    Price per night from

                                    $241

                                    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 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 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 16.22 km from Monterey

                                              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

                                              $1,374

                                              Price per night from

                                              $1,374

                                              Distance approx 7.68 km from Monterey

                                                13

                                                Designer Loft Style Residence

                                                Berkshires / Sheffield

                                                Sheffield house

                                                3 6 7 nights min

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

                                                Price per night from

                                                $516

                                                Price per night from

                                                $516

                                                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

                                                  $377

                                                  Price per night from

                                                  $377

                                                  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

                                                    $516

                                                    Responds fast!
                                                    avg. 1 hour 21 minutes

                                                    Price per night from

                                                    $516

                                                    Distance approx 16.45 km from Monterey

                                                      11

                                                      Beautiful Cottage at the foot of the Berkshires

                                                      New York / Copake Falls

                                                      Copake Falls cottage

                                                      2 4 2 nights min

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

                                                      Price per night from

                                                      $201

                                                      Price per night from

                                                      $201

                                                      Distance approx 11.33 km from Monterey

                                                      (1) Excellent 

                                                        24

                                                        Stockbridge Bowl - Beach Lake Cottage near Tanglewood (1.8 miles) & Kripalu

                                                        Berkshires / Stockbridge

                                                        Stockbridge cottage

                                                        2 4 min stay varies

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

                                                        Price per night from

                                                        $321

                                                        Responds fast!
                                                        avg. 12 minutes

                                                        Price per night from

                                                        $321