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116 Houses

(17) Excellent 

    10

    Stone School Cottage

    Berkshires / Lanesboro

    Lanesboro cottage

    2 5 2 nights min

    • 2 bedrooms
    • sleeps 5
    • 2 nights min
    • Child Friendly
    • Air conditioning
    • Private garden
    “A wonderful experience” My parents really enjoyed their stay. They said everything was wonderful. It is a very charming and has wonderful history. They really thought the baby horses playing in the field across the street was an over the top touch.

    Price per night from

    $178

    Responds fast!
    avg. 2 hours 47 minutes

    Price per night from

    $178

    (5) Excellent 

      31

      Berkshires Waterfront Lakehouse Sanctuary

      Berkshires / Lanesboro

      Lanesboro house

      3 6 2 nights min

      • 3 bedrooms
      • sleeps 6
      • 2 nights min
      • Beach / lakeside relaxation
      • Child Friendly
      • Air conditioning

      Price per night from

      $224

      Responds fast!
      avg. 3 hours 20 minutes

      Price per night from

      $224

        26

        Stunning Private Suite in the Beautiful Berkshires

        Berkshires / Lanesboro

        Lanesboro house

        3 6 2 nights min

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

        Price per night from

        $138

        Price per night from

        $138

          26

          Lakefront Berkshires Cottage - Mins to Skiing!

          Berkshires / Lanesboro

          Lanesboro cottage

          3 10 min stay varies

          • 3 bedrooms
          • sleeps 10
          • min stay varies
          • Ski
          • Child Friendly

          Price per night from

          $287

          Responds fast!
          avg. 32 minutes

          Price per night from

          $287

          Great rentals within 20 miles that match your search

          Distance approx 19.16 km from Lanesboro

            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 9.77 km from Lanesboro

              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 5.06 km from Lanesboro

              (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 10.12 km from Lanesboro

                  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 6.27 km from Lanesboro

                    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 17.45 km from Lanesboro

                    (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 14.76 km from Lanesboro

                        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 14.78 km from Lanesboro

                        (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 19.13 km from Lanesboro

                          (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 14.91 km from Lanesboro

                            (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 19.79 km from Lanesboro

                                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 5.35 km from Lanesboro

                                (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 6.91 km from Lanesboro

                                    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 15.78 km from Lanesboro

                                      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 4.79 km from Lanesboro

                                      (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 11.36 km from Lanesboro

                                          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 14.95 km from Lanesboro

                                            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 12.74 km from Lanesboro

                                            (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 14.82 km from Lanesboro

                                                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 14.78 km from Lanesboro

                                                  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 18.5 km from Lanesboro

                                                    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 19.04 km from Lanesboro

                                                    (4) Very Good 

                                                      18

                                                      Lakefront Berkshires Ski/Summer House, Great Views

                                                      Berkshires / Great Barrington

                                                      Great Barrington house

                                                      4 10 min stay varies

                                                      • 4 bedrooms
                                                      • sleeps 10
                                                      • min stay varies
                                                      • Beach / lakeside relaxation
                                                      • Child Friendly
                                                      • Pet Friendly

                                                      Price per night from

                                                      $215

                                                      Price per night from

                                                      $215

                                                      Distance approx 13.94 km from Lanesboro

                                                      (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 11.8 km from Lanesboro

                                                        (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 14.65 km from Lanesboro

                                                            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 13.94 km from Lanesboro

                                                            (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 1.88 km from Lanesboro

                                                                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

                                                                Distance approx 18.49 km from Lanesboro

                                                                (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 5.26 km from Lanesboro

                                                                    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 13.94 km from Lanesboro

                                                                      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 10.4 km from Lanesboro

                                                                        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 13.18 km from Lanesboro

                                                                        (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 4.88 km from Lanesboro 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 7.65 km from Lanesboro

                                                                            (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