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133 Houses

    24

    3BR Lee House w/ Easy Access to Main Street!

    Berkshires / Lee

    Lee house

    3 10 min stay varies

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

    Price per night from

    $275

    Responds fast!
    avg. 9 minutes

    Price per night from

    $275

      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

      (4) Excellent 

        18

        Lake House

        Berkshires / Lee

        Lee house

        5 9 7 nights min

        • 5 bedrooms
        • sleeps 9
        • 7 nights min
        • Beach / lakeside relaxation
        • Child Friendly
        • Air conditioning

        Price per night from

        $813

        Price per night from

        $813

          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

          $228

          Responds fast!
          avg. 36 minutes

          Price per night from

          $228

          (2) Very Good 

            12

            Berkshires Spacious Comfortable Charming Farmhouse

            Berkshires / Lee

            Lee apartment

            3 8 2 nights min

            • 3 bedrooms
            • sleeps 8
            • 2 nights min
            • Child Friendly
            • Air conditioning
            “lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.
            …see more

            Price per night from

            $344

            Responds fast!
            avg. 1 hour 42 minutes

            Price per night from

            $344

            (1) Excellent 

              13

              The Gatehouse on Golden Hill

              Berkshires / Lee

              Lee house

              4 14 3 nights min

              • 4 bedrooms
              • sleeps 14
              • 3 nights min
              • Child Friendly
              • Air conditioning
              • Private garden

              Price per night from

              $910

              Price per night from

              $910

              (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

                $204

                Responds fast!
                avg. 36 minutes

                Price per night from

                $204

                  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

                  $90

                  Responds fast!
                  avg. 36 minutes

                  Price per night from

                  $90

                  (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

                    (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

                        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

                          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

                            7

                            Deluxe New Home, 2 Master Suites, Tanglewood Area

                            Berkshires / Lee

                            Lee house

                            5 12 3 nights min

                            • 5 bedrooms
                            • sleeps 12
                            • 3 nights min
                            • Child Friendly

                            Price per night from

                            $859

                            Price per night from

                            $859

                            (2) Excellent 

                              22

                              BSO Tanglewood + Jacob's Pillow. Lenox-Stockbridge. 5bdr/6bth. sleeps 24+

                              Berkshires / Lee

                              Lee house

                              5 30 min stay varies

                              • 5 bedrooms
                              • sleeps 30
                              • min stay varies
                              • Nearest beach 3 mi
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $910

                              Responds fast!
                              avg. 3 hours 2 minutes

                              Price per night from

                              $910

                                12

                                Beautiful Berkshire Mtn. Condo with Mountain Views, near Tanglewood, Lakes et al

                                Berkshires / Lee

                                Lee condo

                                3 8 30 nights min

                                • 3 bedrooms
                                • sleeps 8
                                • 30 nights min
                                • Child Friendly

                                Price per night from

                                $247

                                Price per night from

                                $247

                                  23

                                  Newly Renovated Berkshire Cottage near Tanglewood

                                  Berkshires / Lee

                                  Lee cottage

                                  1 2 60 nights min

                                  • 1 bedroom
                                  • sleeps 2
                                  • 60 nights min
                                  • Nearest beach 5 mi
                                  • Air conditioning

                                  Price per night from

                                  $327

                                  Responds fast!
                                  avg. 12 minutes

                                  Price per night from

                                  $327

                                  Great rentals within 20 miles that match your search

                                  Distance approx 4.34 km from Lee Show on Map

                                    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

                                    $284

                                    Responds fast!
                                    avg. 1 hour 18 minutes

                                    Price per night from

                                    $284

                                    Distance approx 9.54 km from Lee

                                      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

                                      $342

                                      Responds fast!
                                      avg. 36 minutes

                                      Price per night from

                                      $342

                                      Distance approx 9.55 km from Lee

                                      (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

                                        $205

                                        Responds fast!
                                        avg. 36 minutes

                                        Price per night from

                                        $205

                                        Distance approx 12.32 km from Lee

                                          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

                                          $350

                                          Price per night from

                                          $350

                                          Distance approx 10.7 km from Lee

                                          (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

                                            $170

                                            Price per night from

                                            $170

                                            Distance approx 3.5 km from Lee Show on Map

                                            (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

                                              $244

                                              Price per night from

                                              $244

                                              Distance approx 8.23 km from Lee

                                                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

                                                $467

                                                Price per night from

                                                $467

                                                Distance approx 9.34 km from Lee

                                                (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

                                                  $342

                                                  Price per night from

                                                  $342

                                                  Distance approx 14.49 km from Lee

                                                    48

                                                    Total Privacy! Tanglewood Retreat With Berkshire Views!

                                                    New York / Hillsdale

                                                    Hillsdale house

                                                    5 14 2 nights min

                                                    • 5 bedrooms
                                                    • sleeps 14
                                                    • 2 nights min
                                                    • Ask about children

                                                    Price per night from

                                                    $681

                                                    Price per night from

                                                    $681

                                                    Distance approx 8.37 km from Lee

                                                      12

                                                      Fabulous Post & Beam Berkshire Rental

                                                      Berkshires / Monterey

                                                      Monterey house

                                                      7 21 nights min

                                                      • sleeps 7
                                                      • 21 nights min
                                                      • Ask about children
                                                      • Car not necessary
                                                      • Ask about pets

                                                      Price per night from

                                                      $203

                                                      Price per night from

                                                      $203

                                                      Distance approx 3.95 km from Lee Show on Map

                                                      (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

                                                        $257

                                                        Responds fast!
                                                        avg. 1 hour 29 minutes

                                                        Price per night from

                                                        $257

                                                        Distance approx 11.37 km from Lee

                                                          22

                                                          BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

                                                          Berkshires / Otis

                                                          Otis house

                                                          6 14 7 nights min

                                                          • 6 bedrooms
                                                          • sleeps 14
                                                          • 7 nights min
                                                          • Ask about children
                                                          • Ask about pets

                                                          Price per night from

                                                          $681

                                                          Price per night from

                                                          $681

                                                          Distance approx 6.07 km from Lee Show on Map

                                                          (39) Excellent 

                                                            20

                                                            Berkshire Farmhouse Vacation

                                                            Berkshires / West Stockbridge

                                                            West Stockbridge house

                                                            5 12 min stay varies

                                                            • 5 bedrooms
                                                            • sleeps 12
                                                            • min stay varies
                                                            • Nearest beach 2 mi
                                                            • Child Friendly
                                                            • Pet Friendly
                                                            “Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the l
                                                            …see more

                                                            Price per night from

                                                            $295

                                                            Price per night from

                                                            $295

                                                            Distance approx 16.84 km from Lee

                                                              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

                                                              $114

                                                              Price per night from

                                                              $114

                                                              Distance approx 3.9 km from Lee Show on Map

                                                                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

                                                                $794

                                                                Price per night from

                                                                $794

                                                                Distance approx 19.25 km from Lee

                                                                  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

                                                                  $193

                                                                  Price per night from

                                                                  $193

                                                                  Distance approx 10.9 km from Lee

                                                                    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

                                                                    $653

                                                                    Price per night from

                                                                    $653

                                                                    Distance approx 17.44 km from Lee

                                                                    (1) Very Good 

                                                                      6

                                                                      Jiminy Peak Ski Resort-Country Village's Best Unit

                                                                      Berkshires / Hancock

                                                                      Hancock apartment

                                                                      2 6 1 night min

                                                                      • 2 bedrooms
                                                                      • sleeps 6
                                                                      • 1 night min
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $292

                                                                      Responds fast!
                                                                      avg. 16 minutes

                                                                      Price per night from

                                                                      $292

                                                                      Distance approx 17.5 km from Lee

                                                                        8

                                                                        7 night Christmas week Wyndham Bentley Brook 2 bdr condo Slopeside

                                                                        Berkshires / Hancock

                                                                        Hancock condo

                                                                        2 8 7 nights min

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

                                                                        Price per night from

                                                                        $233

                                                                        Price per night from

                                                                        $233

                                                                        Distance approx 14.78 km from Lee

                                                                          14

                                                                          Modern Cozy Wooded Retreat

                                                                          New York / Spencertown

                                                                          Spencertown house

                                                                          2 6 30 nights min

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

                                                                          Price per night from

                                                                          $152

                                                                          Price per night from

                                                                          $152

                                                                          Distance approx 11.86 km from Lee

                                                                            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

                                                                            $171

                                                                            Price per night from

                                                                            $171

                                                                            Distance approx 6.37 km from Lee Show on Map

                                                                            (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

                                                                              $325

                                                                              Price per night from

                                                                              $325