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111 Houses

    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

    $719

    Price per night from

    $719

      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

      (6) Excellent 

        23

        Berkshire Blueberry Lodge LLC - Near Jiminy Peak

        New York / Stephentown

        Stephentown lodge

        4 10 2 nights min

        • 4 bedrooms
        • sleeps 10
        • 2 nights min
        • Child Friendly
        • Private garden

        Price per night from

        $430

        Responds fast!
        avg. 1 hour 50 minutes

        Price per night from

        $430

          12

          Ski Cottage in the Berkshire Hills

          New York / Stephentown

          Stephentown house

          3 6 3 nights min

          • 3 bedrooms
          • sleeps 6
          • 3 nights min
          • Child Friendly
          • Air conditioning
          • Ask about pets

          Price per night from

          $285

          Price per night from

          $285

          Great rentals within 20 miles that match your search

          Distance approx 19.08 km from Stephentown

          (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 17.54 km from Stephentown

            (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 16.35 km from Stephentown

                58

                Country estate on 100 acres perfect for families

                New York / Chatham

                Chatham house

                4 6 7 nights min

                • 4 bedrooms
                • sleeps 6
                • 7 nights min
                • Child Friendly

                Price per night from

                $1,140

                Price per night from

                $1,140

                Distance approx 19.07 km from Stephentown

                  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

                  $228

                  Price per night from

                  $228

                  Distance approx 19.49 km from Stephentown

                    8

                    mile hill b and b

                    New York / Kinderhook

                    Kinderhook house

                    2 4 1 night min

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

                    Price per night from

                    $211

                    Price per night from

                    $211

                    Distance approx 14.6 km from Stephentown

                      24

                      Beautiful Berkshire Country Estate

                      New York / Old Chatham

                      Old Chatham house

                      8 16 min stay varies

                      • 8 bedrooms
                      • sleeps 16
                      • min stay varies
                      • Swimming pool
                      • Child Friendly
                      • Air conditioning

                      Price per night from

                      $1,026

                      Price per night from

                      $1,026

                      Distance approx 18.95 km from Stephentown

                      (3) Excellent 

                        15

                        Troy, NY - Collar City Hideaway

                        New York / Troy

                        Troy apartment

                        1 2 2 nights min

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

                        Price per night from

                        $74

                        Responds fast!
                        avg. 32 minutes

                        Price per night from

                        $74

                        Distance approx 3.43 km from Stephentown

                        (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 4.25 km from Stephentown

                            10

                            Vacation Village in the Berkshires Available July 22-29

                            Berkshires / Hancock

                            Hancock condo

                            2 8 7 nights min

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

                            Price per night from

                            $180

                            Price per night from

                            $180

                            Distance approx 19.88 km from Stephentown

                              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 19.08 km from Stephentown

                                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

                                $1,371

                                Price per night from

                                $1,371

                                Distance approx 3.67 km from Stephentown

                                (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

                                  $257

                                  Responds fast!
                                  avg. 1 hour 34 minutes

                                  Price per night from

                                  $257

                                  Distance approx 12.26 km from Stephentown

                                    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 19.08 km from Stephentown

                                    (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 10.48 km from Stephentown

                                        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 17.78 km from Stephentown

                                          14

                                          Modern Cozy Wooded Retreat

                                          New York / Spencertown

                                          Spencertown house

                                          2 6 30 nights min

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

                                          Price per night from

                                          $152

                                          Price per night from

                                          $152

                                          Distance approx 15.34 km from Stephentown

                                          (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

                                            $257

                                            Price per night from

                                            $257

                                            Distance approx 16.98 km from Stephentown

                                              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 16.18 km from Stephentown

                                                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 9.9 km from Stephentown

                                                (4) Excellent 

                                                  10

                                                  Great Vacation House in the Berkshires by Richmond Pond

                                                  Berkshires / Richmond

                                                  Richmond house

                                                  2 6 min stay varies

                                                  • 2 bedrooms
                                                  • sleeps 6
                                                  • min stay varies
                                                  • Beach / lakeside relaxation
                                                  • Child Friendly
                                                  • Air conditioning

                                                  Price per night from

                                                  $213

                                                  Price per night from

                                                  $213

                                                  Distance approx 13.84 km from Stephentown

                                                    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 17.64 km from Stephentown

                                                      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 15.14 km from Stephentown

                                                      (4) Excellent 

                                                        10

                                                        Comfortable Farmhouse in the Berkshires

                                                        Berkshires / West Stockbridge

                                                        West Stockbridge farmhouse

                                                        5 12 2 nights min

                                                        • 5 bedrooms
                                                        • sleeps 12
                                                        • 2 nights min
                                                        • Beach / lakeside relaxation
                                                        • Child Friendly
                                                        • Air conditioning

                                                        Price per night from

                                                        $372

                                                        Responds fast!
                                                        avg. 3 hours 37 minutes

                                                        Price per night from

                                                        $372

                                                        Distance approx 18.71 km from Stephentown

                                                        (1) Excellent 

                                                          17

                                                          Restored 1886 Eyebrow Colonial

                                                          Berkshires / Stockbridge

                                                          Stockbridge house

                                                          2 6 7 nights min

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

                                                          Price per night from

                                                          $245

                                                          Price per night from

                                                          $245

                                                          Distance approx 16.55 km from Stephentown

                                                          (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

                                                            $297

                                                            Price per night from

                                                            $297

                                                            Distance approx 4.11 km from Stephentown

                                                              9

                                                              Larger Than Life 1 BR Sleeps 8 Bentley Brook Resort

                                                              Berkshires / Hancock

                                                              Hancock condo

                                                              1 8 3 nights min

                                                              • 1 bedroom
                                                              • sleeps 8
                                                              • 3 nights min
                                                              • Child Friendly

                                                              Price per night from

                                                              $514

                                                              Price per night from

                                                              $514

                                                              Distance approx 3.87 km from Stephentown

                                                                24

                                                                Cozy Jiminy Peak Area Condo w/Patio & Pool Access!

                                                                Berkshires / Hancock

                                                                Hancock apartment

                                                                2 6 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 6
                                                                • min stay varies
                                                                • Swimming pool
                                                                • Ski
                                                                • Child Friendly

                                                                Price per night from

                                                                $212

                                                                Responds fast!
                                                                avg. 40 minutes

                                                                Price per night from

                                                                $212

                                                                Distance approx 14.05 km from Stephentown

                                                                  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

                                                                  $571

                                                                  Responds fast!
                                                                  avg. 1 hour 19 minutes

                                                                  Price per night from

                                                                  $571

                                                                  Distance approx 17.04 km from Stephentown

                                                                    4

                                                                    Iris Room

                                                                    Berkshires / Stockbridge

                                                                    Stockbridge farmhouse

                                                                    1 2 1 night min

                                                                    • 1 bedroom
                                                                    • sleeps 2
                                                                    • 1 night min
                                                                    • Child Friendly
                                                                    • Pet Friendly
                                                                    • Private garden

                                                                    Price per night from

                                                                    $172

                                                                    Price per night from

                                                                    $172

                                                                    Distance approx 5.73 km from Stephentown

                                                                    (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

                                                                      $2,856

                                                                      Price per night from

                                                                      $2,856

                                                                      Distance approx 19.08 km from Stephentown

                                                                        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 14.6 km from Stephentown

                                                                        (1) Excellent 

                                                                          21

                                                                          Berkshire Country Estate - The Library Suite

                                                                          New York / Old Chatham

                                                                          Old Chatham house

                                                                          2 4 2 nights min

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

                                                                          Price per night from

                                                                          $172

                                                                          Price per night from

                                                                          $172

                                                                          Distance approx 6.99 km from Stephentown

                                                                            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 1.2 km from Stephentown Show on Map

                                                                              23

                                                                              The Dacha: Summer/Skiing House in the Berkshires

                                                                              New York / Treadwell

                                                                              Treadwell apartment

                                                                              2 6 3 nights min

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

                                                                              Price per night from

                                                                              $263

                                                                              Price per night from

                                                                              $263