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136 Houses

    31

    Big Beautiful 7 bedroom 3 bath hot tub pool table

    Berkshires / Pittsfield

    Pittsfield house

    7 18 2 nights min

    • 7 bedrooms
    • sleeps 18
    • 2 nights min
    • Child Friendly
    • Ask about pets

    Price per night from

    $343

    Price per night from

    $343

    Great rentals within 20 miles that match your search

    Distance approx 17.55 km from Pittsfield

      19

      Berkshire Country Estate - Rose Suite

      New York / Old Chatham

      Old Chatham villa

      2 4 2 nights min

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

      Price per night from

      $194

      Price per night from

      $194

      Distance approx 11.32 km from Pittsfield

        7

        Berkshires Cottage Country Retreat

        New York / Stephentown

        Stephentown cottage

        3 6 2 nights min

        • 3 bedrooms
        • sleeps 6
        • 2 nights min
        • Private garden

        Price per night from

        $189

        Responds fast!
        avg. 2 hours 19 minutes

        Price per night from

        $189

        Distance approx 8.02 km from Pittsfield Show on Map

        (3) Very Good 

          14

          2200sf Country House on 16 Acres-2 Miles to Jiminy

          Berkshires / Hancock

          Hancock house

          4 9 2 nights min

          • 4 bedrooms
          • sleeps 9
          • 2 nights min
          • Child Friendly
          • Pet Friendly
          “Great house Jiminy Peak” We (family of 4) stayed a weekend in January 2010 with friends (family of 5). It is a great house, perfect location and the owner is really great to deal with. Highly recommended for everyone with kids. easy drive to the slope

          Price per night from

          $258

          Responds fast!
          avg. 1 hour 34 minutes

          Price per night from

          $258

          Distance approx 6.29 km from Pittsfield

            23

            Renovated 2 bedroom in Heart of Lenox

            Berkshires / Lenox

            Lenox apartment

            2 4 1 night min

            • 2 bedrooms
            • sleeps 4
            • 1 night min
            • Child Friendly
            • Air conditioning

            Price per night from

            $343

            Price per night from

            $343

            Distance approx 7.06 km from Pittsfield Show on Map

              18

              Historic Home on 8.5 Acres

              Berkshires / Dalton

              Dalton house

              3 9 3 nights min

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

              Price per night from

              $458

              Price per night from

              $458

              Distance approx 13.69 km from Pittsfield

              (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

                $326

                Price per night from

                $326

                Distance approx 18.54 km from Pittsfield

                  14

                  ROOM walking distance to Mass MoCa

                  Berkshires / North Adams

                  North Adams apartment

                  1 8 min stay varies

                  • 1 bedroom
                  • sleeps 8
                  • min stay varies
                  • Child Friendly
                  • Air conditioning
                  • Pet Friendly

                  Price per night from

                  $115

                  Price per night from

                  $115

                  Distance approx 18.56 km from Pittsfield

                  (2) Excellent 

                    41

                    Apartment walking distance to Mass MoCa!!

                    Berkshires / North Adams

                    North Adams apartment

                    2 10 min stay varies

                    • 2 bedrooms
                    • sleeps 10
                    • min stay varies
                    • Ski
                    • Child Friendly
                    • Car not necessary

                    Price per night from

                    $200

                    Price per night from

                    $200

                    Distance approx 16.46 km from Pittsfield

                    (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 11.24 km from Pittsfield

                      (39) Excellent 

                        20

                        Berkshire Farmhouse Vacation

                        Berkshires / West Stockbridge

                        West Stockbridge house

                        5 12 min stay varies

                        • 5 bedrooms
                        • sleeps 12
                        • min stay varies
                        • Nearest beach 2 mi
                        • Child Friendly
                        • Pet Friendly
                        “Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the l

                        Price per night from

                        $298

                        Price per night from

                        $298

                        Distance approx 16.03 km from Pittsfield

                          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

                          $4,115

                          Price per night from

                          $4,115

                          Distance approx 8.24 km from Pittsfield Show on Map

                          (2) Excellent 

                            16

                            PanoramicView1000 sq ft Guest Quarters Berkshires

                            Berkshires / Hancock

                            Hancock cottage

                            1 6 2 nights min

                            • 1 bedroom
                            • sleeps 6
                            • 2 nights min
                            • Child Friendly
                            • Air conditioning
                            • Ask about pets

                            Price per night from

                            $166

                            Price per night from

                            $166

                            Distance approx 7.92 km from Pittsfield Show on Map

                              4

                              The Meadow House 4 bdrm 4 bath house

                              New York / Stephentown

                              Stephentown house

                              4 12 2 nights min

                              • 4 bedrooms
                              • sleeps 12
                              • 2 nights min
                              • Ask about children
                              • Air conditioning
                              • Pet Friendly

                              Price per night from

                              $721

                              Price per night from

                              $721

                              Distance approx 18.09 km from Pittsfield

                                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

                                Distance approx 11.99 km from Pittsfield

                                  12

                                  Tanglewood / Berkshires - 2 Bed 2 Bath Apartment

                                  Berkshires / Lee

                                  Lee apartment

                                  2 6 2 nights min

                                  • 2 bedrooms
                                  • sleeps 6
                                  • 2 nights min
                                  • Swimming pool
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $429

                                  Price per night from

                                  $429

                                  Distance approx 7.87 km from Pittsfield Show on Map

                                  (10) Very Good 

                                    21

                                    Wyndham Bentley Brook at Jiminy Peak

                                    Berkshires / Hancock

                                    Hancock hotel apartment

                                    2 8 2 nights min

                                    • 2 bedrooms
                                    • sleeps 8
                                    • 2 nights min
                                    • Swimming pool
                                    • Ski
                                    • Child Friendly

                                    Price per night from

                                    $286

                                    Price per night from

                                    $286

                                    Distance approx 8.73 km from Pittsfield

                                      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 18.72 km from Pittsfield

                                        37

                                        3 BR apartment, walking distance to Mass MoCa

                                        Berkshires / North Adams

                                        North Adams apartment

                                        3 15 min stay varies

                                        • 3 bedrooms
                                        • sleeps 15
                                        • min stay varies
                                        • Ski
                                        • Child Friendly
                                        • Car not necessary

                                        Price per night from

                                        $212

                                        Price per night from

                                        $212

                                        Distance approx 8.98 km from Pittsfield

                                        (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 11.35 km from Pittsfield

                                            7

                                            Deluxe New Home, 2 Master Suites, Tanglewood Area

                                            Berkshires / Lee

                                            Lee house

                                            5 12 3 nights min

                                            • 5 bedrooms
                                            • sleeps 12
                                            • 3 nights min
                                            • Child Friendly

                                            Price per night from

                                            $858

                                            Price per night from

                                            $858

                                            Distance approx 18.57 km from Pittsfield

                                              17

                                              House On Main Street

                                              Berkshires / Williamstown

                                              Williamstown house

                                              4 16 2 nights min

                                              • 4 bedrooms
                                              • sleeps 16
                                              • 2 nights min
                                              • Child Friendly
                                              • Car not necessary
                                              • Air conditioning

                                              Price per night from

                                              $572

                                              Responds fast!
                                              avg. 1 hour 19 minutes

                                              Price per night from

                                              $572

                                              Distance approx 17.97 km from Pittsfield

                                                10

                                                Red Mapple Farm

                                                New York / Malden Bridge

                                                Malden Bridge house

                                                4 8 4 nights min

                                                • 4 bedrooms
                                                • sleeps 8
                                                • 4 nights min
                                                • Ski
                                                • Child Friendly

                                                Price per night from

                                                $503

                                                Price per night from

                                                $503

                                                Distance approx 15.31 km from Pittsfield

                                                (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 10.43 km from Pittsfield

                                                  (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

                                                    $166

                                                    Responds fast!
                                                    avg. 36 minutes

                                                    Price per night from

                                                    $166

                                                    Distance approx 7.98 km from Pittsfield

                                                    (2) Very Good 

                                                      12

                                                      Heart of the Berkshires!

                                                      Berkshires / Lenox

                                                      Lenox house

                                                      3 6 2 nights min

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

                                                      Price per night from

                                                      $258

                                                      Price per night from

                                                      $258

                                                      Distance approx 10.88 km from Pittsfield

                                                        4

                                                        Horse Room

                                                        Berkshires / Stockbridge

                                                        Stockbridge farmhouse

                                                        1 3 1 night min

                                                        • 1 bedroom
                                                        • sleeps 3
                                                        • 1 night min
                                                        • Child Friendly
                                                        • Pet Friendly
                                                        • Private garden

                                                        Price per night from

                                                        $172

                                                        Price per night from

                                                        $172

                                                        Distance approx 10.43 km from Pittsfield

                                                        (1) Excellent 

                                                          8

                                                          Writer's Room at Chestnut Lodge

                                                          Berkshires / Lee

                                                          Lee b and b

                                                          1 2 2 nights min

                                                          • 1 bedroom
                                                          • sleeps 2
                                                          • 2 nights min
                                                          • Nearest beach 8 mi
                                                          • Ask about children
                                                          • Air conditioning

                                                          Price per night from

                                                          $200

                                                          Responds fast!
                                                          avg. 36 minutes

                                                          Price per night from

                                                          $200

                                                          Distance approx 14.92 km from Pittsfield

                                                          (1) Excellent 

                                                            22

                                                            Berkshire Getaway at 'Tofu'S Retreat'

                                                            Berkshires / Alford

                                                            Alford chateau

                                                            3 6 7 nights min

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

                                                            Price per night from

                                                            $246

                                                            Responds fast!
                                                            avg. 1 hour 10 minutes

                                                            Price per night from

                                                            $246

                                                            Distance approx 7.51 km from Pittsfield Show on Map

                                                              13

                                                              Berkshires Summer Rental Beaver Pond Hancock MA

                                                              Berkshires / Hancock

                                                              Hancock condo

                                                              3 6 30 nights min

                                                              • 3 bedrooms
                                                              • sleeps 6
                                                              • 30 nights min
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $115

                                                              Price per night from

                                                              $115

                                                              Distance approx 10.43 km from Pittsfield

                                                                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

                                                                $229

                                                                Responds fast!
                                                                avg. 36 minutes

                                                                Price per night from

                                                                $229

                                                                Distance approx 14.01 km from Pittsfield

                                                                  38

                                                                  Nestled in the Berkshire Hills, The Manor ensures a joyous experience!

                                                                  Berkshires / Adams

                                                                  Adams house

                                                                  7 14 2 nights min

                                                                  • 7 bedrooms
                                                                  • sleeps 14
                                                                  • 2 nights min
                                                                  • Child Friendly
                                                                  • Private garden

                                                                  Price per night from

                                                                  $458

                                                                  Price per night from

                                                                  $458

                                                                  Distance approx 19.3 km from Pittsfield

                                                                    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. 39 minutes

                                                                    Price per night from

                                                                    $126

                                                                    Distance approx 9.44 km from Pittsfield

                                                                    (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 8.42 km from Pittsfield Show on Map

                                                                        19

                                                                        Charming Berkshires lakefront house, great views

                                                                        Berkshires / Cheshire

                                                                        Cheshire house

                                                                        2 5 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 5
                                                                        • min stay varies
                                                                        • Beach / lakeside relaxation
                                                                        • Child Friendly
                                                                        • Car not necessary

                                                                        Price per night from

                                                                        $286

                                                                        Price per night from

                                                                        $286

                                                                        Distance approx 17.9 km from Pittsfield

                                                                          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

                                                                          Distance approx 11.06 km from Pittsfield

                                                                          (1) Very Good 

                                                                            4

                                                                            Golden Triangle in the Berkshires

                                                                            Berkshires / Hancock

                                                                            Hancock house

                                                                            2 4 2 nights min

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

                                                                            Price per night from

                                                                            $2,859

                                                                            Price per night from

                                                                            $2,859

                                                                            Distance approx 19.14 km from Pittsfield

                                                                            (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. 23 minutes

                                                                              Price per night from

                                                                              $216