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113 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. 7 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

        23

        Spacious Lakeside Berkshire Home

        Berkshires / Monterey

        Monterey house

        4 10 3 nights min

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

        Price per night from

        $458

        Price per night from

        $458

          12

          Fabulous Post & Beam Berkshire Rental

          Berkshires / Monterey

          Monterey house

          7 21 nights min

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

          Price per night from

          $205

          Price per night from

          $205

            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. 7 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. 7 minutes

              Price per night from

              $212

              Great rentals within 20 miles that match your search

              Distance approx 8.42 km from Monterey

              (1) Excellent 

                2

                chestnut lodge Queens Room

                Berkshires / Lee

                Lee b and b

                1 2 2 nights min

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

                Price per night from

                $165

                Responds fast!
                avg. 36 minutes

                Price per night from

                $165

                Distance approx 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

                  $1,369

                  Price per night from

                  $1,369

                  Distance approx 8.42 km from Monterey

                    7

                    the BIG room at chestnut lodge

                    Berkshires / Lee

                    Lee b and b

                    1 6 2 nights min

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

                    Price per night from

                    $228

                    Responds fast!
                    avg. 36 minutes

                    Price per night from

                    $228

                    Distance approx 18.99 km from Monterey

                    (3) Excellent 

                      42

                      4 Bedroom Furnished House in Lakeville Connecticut

                      Connecticut / Lakeville

                      Lakeville house

                      4 8 2 nights min

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

                      Price per night from

                      $371

                      Price per night from

                      $371

                      Distance approx 7.91 km from Monterey

                      (4) Excellent 

                        30

                        Gem of the Berkshires, walk to downtown & lake.

                        Berkshires / Great Barrington

                        Great Barrington house

                        5 12 2 nights min

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

                        Price per night from

                        $343

                        Price per night from

                        $343

                        Distance approx 11.74 km from Monterey

                          32

                          RIVERSONG "PENTHOUSE"

                          Berkshires / North Egremont

                          North Egremont room

                          1 2 1 night min

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

                          Price per night from

                          $172

                          Responds fast!
                          avg. 23 minutes

                          Price per night from

                          $172

                          Distance approx 7.87 km from Monterey

                            6

                            Berkshires on the Pond

                            Berkshires / Becket

                            Becket house

                            2 2 4 nights min

                            • 2 bedrooms
                            • sleeps 2
                            • 4 nights min
                            • Nearest beach 16 mi
                            • Ask about children
                            • Private garden

                            Price per night from

                            $143

                            Price per night from

                            $143

                            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 11.96 km from Monterey

                              (2) Excellent 

                                8

                                Cozy & Modern Home -mins from Tanglewood & Kripalu

                                Berkshires / West Stockbridge

                                West Stockbridge apartment

                                2 6 1 night min

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

                                Price per night from

                                $115

                                Responds fast!
                                avg. 1 hour 29 minutes

                                Price per night from

                                $115

                                Distance approx 9.13 km from Monterey

                                  13

                                  Garfield House

                                  Maine / Lee

                                  Lee apartment

                                  2 6 2 nights min

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

                                  Price per night from

                                  $200

                                  Price per night from

                                  $200

                                  Distance approx 10.14 km from Monterey

                                    12

                                    Beautiful Berkshire Mtn. Condo with Mountain Views, near Tanglewood, Lakes et al

                                    Berkshires / Lee

                                    Lee condo

                                    3 8 30 nights min

                                    • 3 bedrooms
                                    • sleeps 8
                                    • 30 nights min
                                    • Child Friendly

                                    Price per night from

                                    $248

                                    Price per night from

                                    $248

                                    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

                                      $858

                                      Responds fast!
                                      avg. 10 minutes

                                      Price per night from

                                      $858

                                      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

                                        $262

                                        Price per night from

                                        $262

                                        Distance approx 17.31 km from Monterey

                                          12

                                          Cottage on East Twin Lakes, Internet Access, A/C.

                                          Connecticut / Salisbury

                                          Salisbury cottage

                                          3 6 7 nights min

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

                                          Price per night from

                                          $180

                                          Price per night from

                                          $180

                                          Distance approx 8.73 km from Monterey

                                          (1) Very Good 

                                            14

                                            Cozy and clean in Gt Barrington- available for October

                                            Berkshires / Great Barrington

                                            Great Barrington house

                                            2 4 3 nights min

                                            • 2 bedrooms
                                            • sleeps 4
                                            • 3 nights min
                                            • Nearest beach 2 mi
                                            • Child Friendly
                                            • Pet Friendly

                                            Price per night from

                                            $172

                                            Responds fast!
                                            avg. 3 hours 37 minutes

                                            Price per night from

                                            $172

                                            Distance approx 16.67 km from Monterey

                                              18

                                              Mountain Views Atop Blueberry Hill on 40 Acres

                                              New York / Austerlitz

                                              Austerlitz house

                                              3 6 2 nights min

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

                                              Price per night from

                                              $229

                                              Price per night from

                                              $229

                                              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

                                                $515

                                                Price per night from

                                                $515

                                                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

                                                  $200

                                                  Price per night from

                                                  $200

                                                  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

                                                    $223

                                                    Price per night from

                                                    $223

                                                    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

                                                      $343

                                                      Price per night from

                                                      $343

                                                      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 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. 10 minutes

                                                          Price per night from

                                                          $258

                                                          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. 2 hours 26 minutes

                                                            Price per night from

                                                            $229

                                                            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 9.15 km from Monterey

                                                              (13) Very Good 

                                                                13

                                                                Quiet Comfortable Cabin 5 Min. Walk to Lake

                                                                Berkshires / Becket

                                                                Becket house

                                                                2 4 2 nights min

                                                                • 2 bedrooms
                                                                • sleeps 4
                                                                • 2 nights min
                                                                • Child Friendly
                                                                • Air conditioning
                                                                • Ask about pets
                                                                “Great winter getaway spot” My girlfriend and I spent new years at this awesome cabin tucked away in Becket, ma. It was quiet, clean, spacious and just about everything we could have asked for. The property was great, there was lots to do in nearby are

                                                                Price per night from

                                                                $171

                                                                Price per night from

                                                                $171

                                                                Distance approx 5.23 km from Monterey

                                                                (1) Excellent 

                                                                  10

                                                                  Romantic Berkshire Cottage on Storybook Estate

                                                                  Berkshires / Tyringham

                                                                  Tyringham cottage

                                                                  1 2 2 nights min

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

                                                                  Price per night from

                                                                  $258

                                                                  Responds fast!
                                                                  avg. 1 hour 43 minutes

                                                                  Price per night from

                                                                  $258

                                                                  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

                                                                    $166

                                                                    Price per night from

                                                                    $166

                                                                    Distance approx 5.23 km from Monterey

                                                                      9

                                                                      Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate

                                                                      Berkshires / Tyringham

                                                                      Tyringham house

                                                                      1 4 2 nights min

                                                                      • 1 bedroom
                                                                      • sleeps 4
                                                                      • 2 nights min
                                                                      • Ask about children
                                                                      • Ask about pets

                                                                      Price per night from

                                                                      $287

                                                                      Responds fast!
                                                                      avg. 1 hour 43 minutes

                                                                      Price per night from

                                                                      $287

                                                                      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

                                                                        $343

                                                                        Responds fast!
                                                                        avg. 12 minutes

                                                                        Price per night from

                                                                        $343

                                                                        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 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 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