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141 Houses

(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

    (5) Excellent 

      32

      Beautiful Vacation Home

      Berkshires / Stockbridge

      Stockbridge house

      4 12 min stay varies

      • 4 bedrooms
      • sleeps 12
      • min stay varies
      • Beach / lakeside relaxation
      • Child Friendly
      • Car not necessary

      Price per night from

      $572

      Price per night from

      $572

      (1) Excellent 

        24

        Stockbridge Bowl - Beach Lake Cottage near Tanglewood (1.8 miles) & Kripalu

        Berkshires / Stockbridge

        Stockbridge cottage

        2 4 min stay varies

        • 2 bedrooms
        • sleeps 4
        • min stay varies
        • Air conditioning

        Price per night from

        $343

        Responds fast!
        avg. 12 minutes

        Price per night from

        $343

          26

          3BD Newly Rennovated Contempoary Near Stockbridge

          Berkshires / Stockbridge

          Stockbridge house

          3 6 3 nights min

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

          Price per night from

          $344

          Price per night from

          $344

            12

            Fabulous NEW Spacious House in the Berkshires Tanglewood

            Berkshires / Stockbridge

            Stockbridge house

            4 8 min stay varies

            • 4 bedrooms
            • sleeps 8
            • min stay varies
            • Child Friendly
            • Air conditioning
            • Pet Friendly

            Price per night from

            $287

            Responds fast!
            avg. 2 hours 1 minutes

            Price per night from

            $287

              22

              Vacation Home on 10 Acres with Pool and Spa

              Berkshires / Stockbridge

              Stockbridge house

              3 6 7 nights min

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

              Price per night from

              $859

              Price per night from

              $859

              (2) Excellent 

                30

                Tranquil 3BR Stockbridge House w/Private Deck

                Berkshires / Stockbridge

                Stockbridge house

                3 6 min stay varies

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

                Price per night from

                $258

                Responds fast!
                avg. 13 minutes

                Price per night from

                $258

                  19

                  One of the Finest Homes and Best location in the Berkshires

                  Berkshires / Stockbridge

                  Stockbridge house

                  4 10 2 nights min

                  • 4 bedrooms
                  • sleeps 10
                  • 2 nights min
                  • Child Friendly
                  • Air conditioning
                  • Pet Friendly

                  Price per night from

                  $802

                  Price per night from

                  $802

                  (6) Excellent 

                    16

                    Family-friendly Cottage Near Lake, Tanglewood

                    Berkshires / Stockbridge

                    Stockbridge cottage

                    3 7 2 nights min

                    • 3 bedrooms
                    • sleeps 7
                    • 2 nights min
                    • Beach / lakeside relaxation
                    • Nearest beach 0.2 mi
                    • Child Friendly

                    Price per night from

                    $327

                    Responds fast!
                    avg. 3 hours 27 minutes

                    Price per night from

                    $327

                      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

                        24

                        Cozy Stockbridge Home - Walk To Golf Course!

                        Berkshires / Stockbridge

                        Stockbridge house

                        2 6 min stay varies

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

                        Price per night from

                        $241

                        Responds fast!
                        avg. 13 minutes

                        Price per night from

                        $241

                          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

                            4

                            Nasturtium 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

                              31

                              |The Escape |STOCKBRIDGE| NEW Home |BERKSHIRES|

                              Berkshires / Stockbridge

                              Stockbridge house

                              4 9 min stay varies

                              • 4 bedrooms
                              • sleeps 9
                              • min stay varies
                              • Child Friendly
                              • Air conditioning
                              • Pet Friendly

                              Price per night from

                              $516

                              Responds fast!
                              avg. 1 hour 21 minutes

                              Price per night from

                              $516

                              (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

                                $327

                                Price per night from

                                $327

                                Great rentals within 20 miles that match your search

                                Distance approx 19.18 km from Stockbridge

                                (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
                                  …see more

                                  Price per night from

                                  $258

                                  Price per night from

                                  $258

                                  Distance approx 8.13 km from Stockbridge

                                  (1) Excellent 

                                    18

                                    Hillhouse Log Cabin

                                    New York / Hillsdale

                                    Hillsdale log cabin

                                    3 13 2 nights min

                                    • 3 bedrooms
                                    • sleeps 13
                                    • 2 nights min
                                    • Beach / lakeside relaxation
                                    • Child Friendly
                                    • Air conditioning
                                    “rest,relax,recharge” It's a Beautiful home that has all the modern conveniences. It's quiet, quaint and had just what I needed to get away from it all. I enjoyed morning coffee on the back deck among the trees and afternoon walks in the woods. A perfe
                                    …see more

                                    Price per night from

                                    $487

                                    Price per night from

                                    $487

                                    Distance approx 12.47 km from Stockbridge

                                    (4) Excellent 

                                      20

                                      Escape to the Berkshires!

                                      Berkshires / Becket

                                      Becket house

                                      4 8 2 nights min

                                      • 4 bedrooms
                                      • sleeps 8
                                      • 2 nights min
                                      • Child Friendly
                                      • Pet Friendly

                                      Price per night from

                                      $315

                                      Price per night from

                                      $315

                                      Distance approx 17.06 km from Stockbridge

                                        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

                                        $722

                                        Price per night from

                                        $722

                                        Distance approx 5.49 km from Stockbridge Show on Map

                                        (30) Excellent 

                                          21

                                          Gartner House, a charming home in Lenox

                                          Berkshires / Lenox

                                          Lenox apartment

                                          4 7 2 nights min

                                          • 4 bedrooms
                                          • sleeps 7
                                          • 2 nights min
                                          • Child Friendly
                                          • Car not necessary
                                          • Ask about pets
                                          “Great Location In Lenox” My family, friends, & I had a wonderful 2 weeks at Gartner House. It is within easy walking distance of nice shops, terrific restaurants, & a friendly library. Not far are Chesterwood, Tanglewood, Jacob's Pillow, Mass MoCa,
                                          …see more

                                          Price per night from

                                          $229

                                          Price per night from

                                          $229

                                          Distance approx 16.72 km from Stockbridge

                                          (2) Excellent 

                                            14

                                            Newly Renovated Lakefront Getaway on Robinson Pond

                                            New York / Copake

                                            Copake house

                                            3 5 3 nights min

                                            • 3 bedrooms
                                            • sleeps 5
                                            • 3 nights min
                                            • Beach / lakeside relaxation
                                            • Nearest beach 0 mi
                                            • Child Friendly

                                            Price per night from

                                            $229

                                            Responds fast!
                                            avg. 2 hours 41 minutes

                                            Price per night from

                                            $229

                                            Distance approx 16.48 km from Stockbridge

                                              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 19.72 km from Stockbridge

                                                16

                                                Escape to Avalon Cottage in the Hudson Valley

                                                New York / Craryville

                                                Craryville house

                                                3 5 3 nights min

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

                                                Price per night from

                                                $166

                                                Price per night from

                                                $166

                                                Distance approx 6.75 km from Stockbridge

                                                (24) Excellent 

                                                  18

                                                  Berkshires: Romantic Cottage with spectacular view

                                                  Berkshires / Great Barrington

                                                  Great Barrington cottage

                                                  1 3 min stay varies

                                                  • 1 bedroom
                                                  • sleeps 3
                                                  • min stay varies
                                                  • Nearest beach 2 mi
                                                  • Swimming pool
                                                  • Ask about children
                                                  “Perhaps the most relaxing vacation I've ever had” The Sigels' cottage was absolutely perfect for us. My husband and I were looking for a nice quiet 4-night stay while our 7-yr-old twins visited with their grandparents. When we arrived everything loo
                                                  …see more

                                                  Price per night from

                                                  $228

                                                  Price per night from

                                                  $228

                                                  Distance approx 5.44 km from Stockbridge Show on Map

                                                  (7) Excellent 

                                                    18

                                                    To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.

                                                    Berkshires / West Stockbridge

                                                    West Stockbridge house

                                                    3 8 min stay varies

                                                    • 3 bedrooms
                                                    • sleeps 8
                                                    • min stay varies
                                                    • Beach / lakeside relaxation
                                                    • Child Friendly
                                                    • Pet Friendly
                                                    “A memorable weekend getaway includes the most perfect house..” My husband and I had the pleasure to rent out this house last summer with another married couple and their son. Although our daughter and their son truly enjoyed Tanglewood and our visits
                                                    …see more

                                                    Price per night from

                                                    $377

                                                    Price per night from

                                                    $377

                                                    Distance approx 8.37 km from Stockbridge

                                                    (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

                                                      $217

                                                      Responds fast!
                                                      avg. 33 minutes

                                                      Price per night from

                                                      $217

                                                      Distance approx 4.83 km from Stockbridge

                                                        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

                                                        $4,122

                                                        Price per night from

                                                        $4,122

                                                        Distance approx 12.03 km from Stockbridge

                                                          15

                                                          S. Berkshires Mountain Treehouse • Views • Privacy

                                                          Berkshires / Great Barrington

                                                          Great Barrington house

                                                          2 4 14 nights min

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

                                                          Price per night from

                                                          $213

                                                          Responds fast!
                                                          avg. 1 hour 16 minutes

                                                          Price per night from

                                                          $213

                                                          Distance approx 5.76 km from Stockbridge

                                                            10

                                                            ground floor garden room

                                                            Berkshires / Lee

                                                            Lee b and b

                                                            1 2 2 nights min

                                                            • 1 bedroom
                                                            • sleeps 2
                                                            • 2 nights min
                                                            • Nearest beach 5 mi
                                                            • Ask about children
                                                            • Ask about pets

                                                            Price per night from

                                                            $91

                                                            Responds fast!
                                                            avg. 36 minutes

                                                            Price per night from

                                                            $91

                                                            Distance approx 13.15 km from Stockbridge

                                                            (3) Excellent 

                                                              11

                                                              Overnight at Althouse -Higgins

                                                              New York / Hillsdale

                                                              Hillsdale apartment

                                                              2 4 2 nights min

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

                                                              Price per night from

                                                              $201

                                                              Price per night from

                                                              $201

                                                              Distance approx 17.52 km from Stockbridge

                                                              (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

                                                                Distance approx 3.59 km from Stockbridge Show on Map

                                                                  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

                                                                  $201

                                                                  Price per night from

                                                                  $201

                                                                  Distance approx 3.76 km from Stockbridge Show on Map

                                                                  (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 2.83 km from Stockbridge Show on Map

                                                                      6

                                                                      Rustic Rivers end room in the barn at chestnut lodge

                                                                      Berkshires / Lee

                                                                      Lee barn

                                                                      1 4 2 nights min

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

                                                                      Price per night from

                                                                      $178

                                                                      Responds fast!
                                                                      avg. 36 minutes

                                                                      Price per night from

                                                                      $178

                                                                      Distance approx 17.35 km from Stockbridge

                                                                        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

                                                                        $195

                                                                        Price per night from

                                                                        $195

                                                                        Distance approx 12.62 km from Stockbridge

                                                                        (1) Excellent 

                                                                          14

                                                                          The perfect Southern Berkshire winter vacation esc

                                                                          Berkshires / Sheffield

                                                                          Sheffield house

                                                                          4 10 7 nights min

                                                                          • 4 bedrooms
                                                                          • sleeps 10
                                                                          • 7 nights min
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $573

                                                                          Price per night from

                                                                          $573

                                                                          Distance approx 12.01 km from Stockbridge

                                                                            14

                                                                            Modern Cozy Wooded Retreat

                                                                            New York / Spencertown

                                                                            Spencertown house

                                                                            2 6 30 nights min

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

                                                                            Price per night from

                                                                            $153

                                                                            Price per night from

                                                                            $153

                                                                            Distance approx 12.98 km from Stockbridge

                                                                            (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
                                                                              …see more

                                                                              Price per night from

                                                                              $171

                                                                              Price per night from

                                                                              $171