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53 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. 56 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

        25

        NEW! Monterey Home w/Porch by Beach & State Parks!

        Berkshires / Monterey

        Monterey house

        3 7 min stay varies

        • 3 bedrooms
        • sleeps 7
        • min stay varies
        • Ski
        • Child Friendly
        • Pet Friendly

        Price per night from

        $229

        Responds fast!
        avg. 56 minutes

        Price per night from

        $229

          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. 56 minutes

          Price per night from

          $212

          Great rentals within 20 miles that match your search

          Distance approx 10.58 km from Monterey

            36

            Spacious Berkshires Home w/ Pool & Patio!

            Berkshires / North Egremont

            North Egremont house

            5 10 2 nights min

            • 5 bedrooms
            • sleeps 10
            • 2 nights min
            • Swimming pool
            • Ski
            • Child Friendly

            Price per night from

            $853

            Responds fast!
            avg. 24 minutes

            Price per night from

            $853

            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

              $341

              Price per night from

              $341

              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 9.62 km from Monterey

                (13) Excellent 

                  17

                  Serene Lakefront Cottage

                  Berkshires / Becket

                  Becket house

                  2 6 min stay varies

                  • 2 bedrooms
                  • sleeps 6
                  • min stay varies
                  • Child Friendly
                  • Air conditioning
                  • Pet Friendly
                  “Peaceful country escape” Really enjoyed the stay here. Very complete driving and house directions provided by the owners, and checking in - even at a late hour - was a breeze. The house was very clean, woods and lake were beautiful. Many of the hou

                  Price per night from

                  $171

                  Price per night from

                  $171

                  Distance approx 3.48 km from Monterey Show on Map

                    24

                    Rustic Berkshires Cottage w/ Views of Lake Buel!

                    Berkshires / New Marlborough

                    New Marlborough cottage

                    1 2 7 nights min

                    • 1 bedroom
                    • sleeps 2
                    • 7 nights min
                    • Pet Friendly

                    Price per night from

                    $126

                    Responds fast!
                    avg. 1 hour 33 minutes

                    Price per night from

                    $126

                    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

                      $216

                      Responds fast!
                      avg. 11 minutes

                      Price per night from

                      $216

                      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 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

                          $4,111

                          Price per night from

                          $4,111

                          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

                            $217

                            Price per night from

                            $217

                            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 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 4.77 km from Monterey

                                  10

                                  Country Victorian Serenity in the Berkshires

                                  Berkshires / New Marlborough

                                  New Marlborough house

                                  4 6 7 nights min

                                  • 4 bedrooms
                                  • sleeps 6
                                  • 7 nights min
                                  • Suitable for children age 5+
                                  • Private garden

                                  Price per night from

                                  $263

                                  Price per night from

                                  $263

                                  Distance approx 10.65 km from Monterey

                                  (2) Excellent 

                                    30

                                    Tranquil 3BR Stockbridge House w/Private Deck

                                    Berkshires / Stockbridge

                                    Stockbridge house

                                    3 6 min stay varies

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

                                    Price per night from

                                    $258

                                    Responds fast!
                                    avg. 56 minutes

                                    Price per night from

                                    $258

                                    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. 56 minutes

                                      Price per night from

                                      $275

                                      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

                                        $207

                                        Responds fast!
                                        avg. 56 minutes

                                        Price per night from

                                        $207

                                        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

                                          $245

                                          Price per night from

                                          $245

                                          Distance approx 9.09 km from Monterey

                                            24

                                            Cozy Stockbridge Home - Walk To Golf Course!

                                            Berkshires / Stockbridge

                                            Stockbridge house

                                            2 6 min stay varies

                                            • 2 bedrooms
                                            • sleeps 6
                                            • min stay varies
                                            • Ski
                                            • Child Friendly
                                            • Air conditioning

                                            Price per night from

                                            $241

                                            Responds fast!
                                            avg. 56 minutes

                                            Price per night from

                                            $241

                                            Distance approx 9.36 km from Monterey

                                              24

                                              East Otis Reservoir Cabin w/ Porch - Walk to Lake!

                                              Berkshires / Otis

                                              Otis log cabin

                                              2 4 3 nights min

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

                                              Price per night from

                                              $115

                                              Responds fast!
                                              avg. 56 minutes

                                              Price per night from

                                              $115

                                              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 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 9.18 km from Monterey

                                                    6

                                                    Rustic Rivers end room in the barn at chestnut lodge

                                                    Berkshires / Lee

                                                    Lee barn

                                                    1 4 2 nights min

                                                    • 1 bedroom
                                                    • sleeps 4
                                                    • 2 nights min
                                                    • Ask about pets
                                                    • Private garden

                                                    Price per night from

                                                    $178

                                                    Responds fast!
                                                    avg. 36 minutes

                                                    Price per night from

                                                    $178

                                                    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 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 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 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 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. 56 minutes

                                                              Price per night from

                                                              $373

                                                              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

                                                                $487

                                                                Price per night from

                                                                $487

                                                                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

                                                                  $1,375

                                                                  Price per night from

                                                                  $1,375

                                                                  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 19.88 km from Monterey

                                                                      26

                                                                      NEW! Charming Berkshires Cottage on Ashmere Lake

                                                                      Berkshires / Hinsdale

                                                                      Hinsdale cottage

                                                                      3 6 3 nights min

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

                                                                      Price per night from

                                                                      $224

                                                                      Responds fast!
                                                                      avg. 3 hours 8 minutes

                                                                      Price per night from

                                                                      $224

                                                                      Distance approx 16.38 km from Monterey

                                                                        25

                                                                        Historic Huntington Home - Walk to Westfield River

                                                                        Hampshire County / Huntington

                                                                        Huntington house

                                                                        3 7 min stay varies

                                                                        • 3 bedrooms
                                                                        • sleeps 7
                                                                        • min stay varies
                                                                        • Child Friendly
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $218

                                                                        Responds fast!
                                                                        avg. 28 minutes

                                                                        Price per night from

                                                                        $218

                                                                        Distance approx 10.3 km from Monterey

                                                                          26

                                                                          NEW! Lakefront Berkshires House w/Deck, Dock +Boat

                                                                          Berkshires / Housatonic

                                                                          Housatonic house

                                                                          4 10 min stay varies

                                                                          • 4 bedrooms
                                                                          • sleeps 10
                                                                          • min stay varies
                                                                          • Ski
                                                                          • Child Friendly
                                                                          • Pet Friendly

                                                                          Price per night from

                                                                          $212

                                                                          Responds fast!
                                                                          avg. 27 minutes

                                                                          Price per night from

                                                                          $212

                                                                          Distance approx 9.26 km from Monterey

                                                                          (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 13.35 km from Monterey

                                                                              24

                                                                              Waterfront Home in Tolland w/ Deck - Steps to Lake

                                                                              Connecticut / West Hartland

                                                                              West Hartland log cabin

                                                                              3 8 min stay varies

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

                                                                              Price per night from

                                                                              $264

                                                                              Responds fast!
                                                                              avg. 27 minutes

                                                                              Price per night from

                                                                              $264