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113 Houses

(4) Excellent 

    24

    Waterfront Cottage - 10 Mins to Great Barrington!

    Berkshires / New Marlborough

    New Marlborough cottage

    2 4 min stay varies

    • 2 bedrooms
    • sleeps 4
    • min stay varies
    • Ski

    Price per night from

    $207

    Responds fast!
    avg. 58 minutes

    Price per night from

    $207

      24

      Rustic Berkshires Cottage w/ Views of Lake Buel!

      Berkshires / New Marlborough

      New Marlborough cottage

      1 2 7 nights min

      • 1 bedroom
      • sleeps 2
      • 7 nights min
      • Pet Friendly

      Price per night from

      $126

      Responds fast!
      avg. 8 minutes

      Price per night from

      $126

        10

        Country Victorian Serenity in the Berkshires

        Berkshires / New Marlborough

        New Marlborough house

        4 6 7 nights min

        • 4 bedrooms
        • sleeps 6
        • 7 nights min
        • Suitable for children age 5+
        • Private garden

        Price per night from

        $263

        Price per night from

        $263

          35

          Charming Private Guest Suite in Historic Village in the Berkshires

          Berkshires / New Marlborough

          New Marlborough studio

          Studio 2 1 night min

          • Studio
          • sleeps 2
          • 1 night min

          Price per night from

          $109

          Price per night from

          $109

            17

            Picturesque 19th century home on 3 private acres

            Berkshires / New Marlborough

            New Marlborough house

            4 7 min stay varies

            • 4 bedrooms
            • sleeps 7
            • min stay varies
            • Child Friendly
            • Private garden

            Price per night from

            $172

            Price per night from

            $172

            Great rentals within 20 miles that match your search

            Distance approx 5.82 km from New Marlborough

              32

              Berkshire Home on Lake Garfield w/Dock & Boats

              Berkshires / Monterey

              Monterey house

              4 12 min stay varies

              • 4 bedrooms
              • sleeps 12
              • min stay varies
              • Ski
              • Child Friendly
              • Air conditioning

              Price per night from

              $345

              Responds fast!
              avg. 58 minutes

              Price per night from

              $345

              Distance approx 15.25 km from New Marlborough

                5

                Cozy Modern Condo for the Berkshires

                Berkshires / West Stockbridge

                West Stockbridge condo

                2 6 1 night min

                • 2 bedrooms
                • sleeps 6
                • 1 night min
                • Child Friendly
                • Air conditioning
                • Pet Friendly

                Price per night from

                $288

                Responds fast!
                avg. 1 hour 23 minutes

                Price per night from

                $288

                Distance approx 14.32 km from New Marlborough

                  18

                  Spacious wooded home

                  Berkshires / Becket

                  Becket house

                  4 12 3 nights min

                  • 4 bedrooms
                  • sleeps 12
                  • 3 nights min
                  • Beach / lakeside relaxation
                  • Private garden

                  Price per night from

                  $225

                  Price per night from

                  $225

                  Distance approx 6.29 km from New Marlborough

                    24

                    Beautiful Lakefront Berkshire Rental

                    Berkshires / Monterey

                    Monterey house

                    5 6 7 nights min

                    • 5 bedrooms
                    • sleeps 6
                    • 7 nights min
                    • Beach / lakeside relaxation
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $489

                    Price per night from

                    $489

                    Distance approx 16.97 km from New Marlborough

                      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

                      $1,381

                      Price per night from

                      $1,381

                      Distance approx 11.49 km from New Marlborough

                      (4) Very Good 

                        18

                        Lakefront Berkshires Ski/Summer House, Great Views

                        Berkshires / Great Barrington

                        Great Barrington house

                        4 10 min stay varies

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

                        Price per night from

                        $216

                        Price per night from

                        $216

                        Distance approx 12.46 km from New Marlborough

                        (1) Excellent 

                          11

                          Riverwood - Cozy Carriage House in the Woods

                          Connecticut / Falls Village

                          Falls Village apartment

                          1 2 2 nights min

                          • 1 bedroom
                          • sleeps 2
                          • 2 nights min
                          • Ask about children
                          • Air conditioning
                          • Private garden

                          Price per night from

                          $259

                          Price per night from

                          $259

                          Distance approx 6.25 km from New Marlborough

                            23

                            Spacious Lakeside Berkshire Home

                            Berkshires / Monterey

                            Monterey house

                            4 10 3 nights min

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

                            Price per night from

                            $460

                            Price per night from

                            $460

                            Distance approx 17.14 km from New Marlborough

                            (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

                              $379

                              Price per night from

                              $379

                              Distance approx 8.06 km from New Marlborough

                              (4) Excellent 

                                30

                                Gem of the Berkshires, walk to downtown & lake.

                                Berkshires / Great Barrington

                                Great Barrington house

                                5 12 2 nights min

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

                                Price per night from

                                $345

                                Price per night from

                                $345

                                Distance approx 4.56 km from New Marlborough

                                  13

                                  Designer Loft Style Residence

                                  Berkshires / Sheffield

                                  Sheffield house

                                  3 6 7 nights min

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

                                  Price per night from

                                  $516

                                  Responds fast!
                                  avg. 3 hours 46 minutes

                                  Price per night from

                                  $516

                                  Distance approx 13.66 km from New Marlborough

                                  (3) Excellent 

                                    42

                                    4 Bedroom Furnished House in Lakeville Connecticut

                                    Connecticut / Lakeville

                                    Lakeville house

                                    4 8 2 nights min

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

                                    Price per night from

                                    $374

                                    Price per night from

                                    $374

                                    Distance approx 11.15 km from New Marlborough

                                      32

                                      RIVERSONG "PENTHOUSE"

                                      Berkshires / North Egremont

                                      North Egremont room

                                      1 2 1 night min

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

                                      Price per night from

                                      $172

                                      Responds fast!
                                      avg. 33 minutes

                                      Price per night from

                                      $172

                                      Distance approx 10.17 km from New Marlborough

                                      (2) Excellent 

                                        24

                                        Country Elegance in the Berkshires

                                        Berkshires / Great Barrington

                                        Great Barrington house

                                        4 12 2 nights min

                                        • 4 bedrooms
                                        • sleeps 12
                                        • 2 nights min
                                        • Nearest beach 0 mi
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $745

                                        Responds fast!
                                        avg. 2 hours 46 minutes

                                        Price per night from

                                        $745

                                        Distance approx 13.86 km from New Marlborough

                                          24

                                          Waterfront Home in Tolland w/ Deck - Steps to Lake

                                          Connecticut / West Hartland

                                          West Hartland log cabin

                                          3 8 min stay varies

                                          • 3 bedrooms
                                          • sleeps 8
                                          • min stay varies
                                          • Ski
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $264

                                          Responds fast!
                                          avg. 58 minutes

                                          Price per night from

                                          $264

                                          Distance approx 13.12 km from New Marlborough

                                            6

                                            Berkshires on the Pond

                                            Berkshires / Becket

                                            Becket house

                                            2 2 4 nights min

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

                                            Price per night from

                                            $144

                                            Price per night from

                                            $144

                                            Distance approx 10.31 km from New Marlborough

                                            (1) Excellent 

                                              10

                                              Romantic Berkshire Cottage on Storybook Estate

                                              Berkshires / Tyringham

                                              Tyringham cottage

                                              1 2 2 nights min

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

                                              Price per night from

                                              $258

                                              Responds fast!
                                              avg. 1 hour 29 minutes

                                              Price per night from

                                              $258

                                              Distance approx 11.3 km from New Marlborough

                                                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

                                                $430

                                                Price per night from

                                                $430

                                                Distance approx 8.51 km from New Marlborough

                                                  36

                                                  Spacious Berkshires Home w/ Pool & Patio!

                                                  Berkshires / North Egremont

                                                  North Egremont house

                                                  5 10 2 nights min

                                                  • 5 bedrooms
                                                  • sleeps 10
                                                  • 2 nights min
                                                  • Swimming pool
                                                  • Ski
                                                  • Child Friendly

                                                  Price per night from

                                                  $858

                                                  Responds fast!
                                                  avg. 9 minutes

                                                  Price per night from

                                                  $858

                                                  Distance approx 15.04 km from New Marlborough

                                                  (1) Excellent 

                                                    24

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

                                                    Berkshires / Stockbridge

                                                    Stockbridge cottage

                                                    2 4 min stay varies

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

                                                    Price per night from

                                                    $343

                                                    Responds fast!
                                                    avg. 12 minutes

                                                    Price per night from

                                                    $343

                                                    Distance approx 13.52 km from New Marlborough

                                                      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

                                                      $230

                                                      Responds fast!
                                                      avg. 36 minutes

                                                      Price per night from

                                                      $230

                                                      Distance approx 13.52 km from New Marlborough

                                                      (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

                                                        $205

                                                        Responds fast!
                                                        avg. 36 minutes

                                                        Price per night from

                                                        $205

                                                        Distance approx 17.79 km from New Marlborough

                                                          20

                                                          New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)

                                                          Berkshires / Richmond

                                                          Richmond house

                                                          3 6 7 nights min

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

                                                          Price per night from

                                                          $572

                                                          Price per night from

                                                          $572

                                                          Distance approx 10.31 km from New Marlborough

                                                            9

                                                            Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate

                                                            Berkshires / Tyringham

                                                            Tyringham house

                                                            1 4 2 nights min

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

                                                            Price per night from

                                                            $287

                                                            Responds fast!
                                                            avg. 1 hour 29 minutes

                                                            Price per night from

                                                            $287

                                                            Distance approx 13.52 km from New Marlborough

                                                            (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

                                                              $167

                                                              Responds fast!
                                                              avg. 36 minutes

                                                              Price per night from

                                                              $167

                                                              Distance approx 13.54 km from New Marlborough

                                                              (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. 58 minutes

                                                                Price per night from

                                                                $258

                                                                Distance approx 13.84 km from New Marlborough

                                                                (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

                                                                  $87

                                                                  Price per night from

                                                                  $87

                                                                  Distance approx 13.51 km from New Marlborough

                                                                    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 13.86 km from New Marlborough

                                                                      15

                                                                      House share/room for rent

                                                                      Berkshires / Lee

                                                                      Lee room

                                                                      1 1 1 night min

                                                                      • 1 bedroom
                                                                      • sleeps 1
                                                                      • 1 night min
                                                                      • Beach / lakeside relaxation
                                                                      • Nearest beach 3 mi

                                                                      Price per night from

                                                                      $77

                                                                      Price per night from

                                                                      $77

                                                                      Distance approx 9.39 km from New Marlborough

                                                                      (1) Very Good 

                                                                        14

                                                                        Cozy and clean in Gt Barrington- available for October

                                                                        Berkshires / Great Barrington

                                                                        Great Barrington house

                                                                        2 4 3 nights min

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

                                                                        Price per night from

                                                                        $173

                                                                        Responds fast!
                                                                        avg. 3 hours 37 minutes

                                                                        Price per night from

                                                                        $173

                                                                        Distance approx 12.26 km from New Marlborough

                                                                          24

                                                                          East Otis Reservoir Cabin w/ Porch - Walk to Lake!

                                                                          Berkshires / Otis

                                                                          Otis log cabin

                                                                          2 4 3 nights min

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

                                                                          Price per night from

                                                                          $115

                                                                          Responds fast!
                                                                          avg. 35 minutes

                                                                          Price per night from

                                                                          $115

                                                                          Distance approx 17.48 km from New Marlborough

                                                                            10

                                                                            The Barn at Copake Lake

                                                                            New York / Craryville

                                                                            Craryville barn

                                                                            3 14 2 nights min

                                                                            • 3 bedrooms
                                                                            • sleeps 14
                                                                            • 2 nights min
                                                                            • Child Friendly

                                                                            Price per night from

                                                                            $689

                                                                            Price per night from

                                                                            $689

                                                                            Distance approx 11.99 km from New Marlborough

                                                                              12

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

                                                                              Connecticut / Salisbury

                                                                              Salisbury cottage

                                                                              3 6 7 nights min

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

                                                                              Price per night from

                                                                              $180

                                                                              Price per night from

                                                                              $180