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121 Houses

(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

    (13) Very Good 

      13

      Quiet Comfortable Cabin 5 Min. Walk to Lake

      Berkshires / Becket

      Becket house

      2 4 2 nights min

      • 2 bedrooms
      • sleeps 4
      • 2 nights min
      • Child Friendly
      • Air conditioning
      • Ask about pets
      “Great winter getaway spot” My girlfriend and I spent new years at this awesome cabin tucked away in Becket, ma. It was quiet, clean, spacious and just about everything we could have asked for. The property was great, there was lots to do in nearby are
      …see more

      Price per night from

      $171

      Price per night from

      $171

        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

        $224

        Price per night from

        $224

          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

            30

            NEW! Becket Home on 11 Acres w/ Swimming Pond!

            Berkshires / Becket

            Becket house

            3 8 min stay varies

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

            Price per night from

            $373

            Responds fast!
            avg. 47 minutes

            Price per night from

            $373

            (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

              $166

              Price per night from

              $166

              Great rentals within 20 miles that match your search

              Distance approx 13.86 km from Becket

                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. 18 minutes

                Price per night from

                $126

                Distance approx 9.94 km from Becket

                (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 15.13 km from Becket

                  (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 36 minutes

                    Price per night from

                    $745

                    Distance approx 14.59 km from Becket

                      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

                      $344

                      Price per night from

                      $344

                      Distance approx 14.24 km from Becket

                      (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 10.35 km from Becket

                          23

                          Spacious Lakeside Berkshire Home

                          Berkshires / Monterey

                          Monterey house

                          4 10 3 nights min

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

                          Price per night from

                          $458

                          Price per night from

                          $458

                          Distance approx 19.79 km from Becket

                            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

                            $859

                            Responds fast!
                            avg. 47 minutes

                            Price per night from

                            $859

                            Distance approx 15.97 km from Becket

                            (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

                              $344

                              Price per night from

                              $344

                              Distance approx 18.63 km from Becket

                                7

                                Starlight Llama - The Pink Room

                                Hampshire County / Northampton

                                Northampton b and b

                                1 2 2 nights min

                                • 1 bedroom
                                • sleeps 2
                                • 2 nights min

                                Price per night from

                                $132

                                Responds fast!
                                avg. 1 hour 26 minutes

                                Price per night from

                                $132

                                Distance approx 9.48 km from Becket

                                  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 19.2 km from Becket

                                    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

                                    $160

                                    Responds fast!
                                    avg. 34 minutes

                                    Price per night from

                                    $160

                                    Distance approx 7.38 km from Becket

                                    (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 15.93 km from Becket

                                        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

                                        Distance approx 9.98 km from Becket

                                        (2) Excellent 

                                          10

                                          Heart of Lenox

                                          Berkshires / Lenox

                                          Lenox house

                                          2 4 2 nights min

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

                                          Price per night from

                                          $201

                                          Responds fast!
                                          avg. 2 hours 17 minutes

                                          Price per night from

                                          $201

                                          Distance approx 10.91 km from Becket

                                            25

                                            Historic Huntington Home - Walk to Westfield River

                                            Hampshire County / Huntington

                                            Huntington house

                                            3 7 min stay varies

                                            • 3 bedrooms
                                            • sleeps 7
                                            • min stay varies
                                            • Child Friendly
                                            • Air conditioning

                                            Price per night from

                                            $218

                                            Responds fast!
                                            avg. 47 minutes

                                            Price per night from

                                            $218

                                            Distance approx 10.49 km from Becket

                                              26

                                              3BD Newly Rennovated Contempoary Near Stockbridge

                                              Berkshires / Stockbridge

                                              Stockbridge house

                                              3 6 min stay varies

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

                                              Price per night from

                                              $344

                                              Price per night from

                                              $344

                                              Distance approx 5.68 km from Becket

                                              (1) Excellent 

                                                2

                                                chestnut lodge Queens Room

                                                Berkshires / Lee

                                                Lee b and b

                                                1 2 2 nights min

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

                                                Price per night from

                                                $166

                                                Responds fast!
                                                avg. 36 minutes

                                                Price per night from

                                                $166

                                                Distance approx 8.04 km from Becket

                                                  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 18.63 km from Becket

                                                    8

                                                    Starlight Llama - The Lavender Room

                                                    Hampshire County / Northampton

                                                    Northampton b and b

                                                    1 2 2 nights min

                                                    • 1 bedroom
                                                    • sleeps 2
                                                    • 2 nights min
                                                    • Child Friendly

                                                    Price per night from

                                                    $132

                                                    Responds fast!
                                                    avg. 1 hour 26 minutes

                                                    Price per night from

                                                    $132

                                                    Distance approx 10.12 km from Becket

                                                      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

                                                      $344

                                                      Price per night from

                                                      $344

                                                      Distance approx 11.79 km from Becket

                                                        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

                                                        Distance approx 19.68 km from Becket

                                                          13

                                                          Berkshires Summer Rental Beaver Pond Hancock MA

                                                          Berkshires / Hancock

                                                          Hancock condo

                                                          3 6 30 nights min

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

                                                          Price per night from

                                                          $115

                                                          Price per night from

                                                          $115

                                                          Distance approx 13.63 km from Becket

                                                            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

                                                            $573

                                                            Price per night from

                                                            $573

                                                            Distance approx 19.48 km from Becket

                                                              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

                                                              $516

                                                              Price per night from

                                                              $516

                                                              Distance approx 19.71 km from Becket

                                                                6

                                                                Thanksgiving week lux condo/4 Berkshires

                                                                Berkshires / Williamstown

                                                                Williamstown condo

                                                                2 4 7 nights min

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

                                                                Price per night from

                                                                $263

                                                                Price per night from

                                                                $263

                                                                Distance approx 8.87 km from Becket

                                                                  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 17.24 km from Becket

                                                                  (1) Excellent 

                                                                    22

                                                                    Berkshire Getaway at 'Tofu'S Retreat'

                                                                    Berkshires / Alford

                                                                    Alford chateau

                                                                    3 6 7 nights min

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

                                                                    Price per night from

                                                                    $247

                                                                    Responds fast!
                                                                    avg. 1 hour 10 minutes

                                                                    Price per night from

                                                                    $247

                                                                    Distance approx 16.23 km from Becket

                                                                      24

                                                                      Rustic Goshen Cabin w/ Fire Pit, BBQ & Great Deck!

                                                                      Hampshire County / Goshen

                                                                      Goshen log cabin

                                                                      2 8 min stay varies

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

                                                                      Price per night from

                                                                      $241

                                                                      Responds fast!
                                                                      avg. 1 hour 7 minutes

                                                                      Price per night from

                                                                      $241

                                                                      Distance approx 19.76 km from Becket

                                                                      (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 12.56 km from Becket

                                                                          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 17.59 km from Becket

                                                                            21

                                                                            Private Berkshire Estate w/Pool & Tennis Court

                                                                            Berkshires / Great Barrington

                                                                            Great Barrington house

                                                                            4 12 min stay varies

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

                                                                            Price per night from

                                                                            $659

                                                                            Price per night from

                                                                            $659

                                                                            Distance approx 15.64 km from Becket

                                                                              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