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136 Houses

    24

    NEW! Cozy Lenox Home 1.5 Mi. to Tanglewood Music!

    Berkshires / Lenox

    Lenox house

    3 6 3 nights min

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

    Price per night from

    $264

    Responds fast!
    avg. 58 minutes

    Price per night from

    $264

    (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

      (1) Excellent 

        34

        INTERIOR DESIGNERS BOTANICAL GARDENS

        Berkshires / Lenox

        Lenox cottage

        1 5 2 nights min

        • 1 bedroom
        • sleeps 5
        • 2 nights min
        • Nearest beach 3 mi
        • Child Friendly
        • Air conditioning

        Price per night from

        $132

        Price per night from

        $132

        (2) Very Good 

          12

          Heart of the Berkshires!

          Berkshires / Lenox

          Lenox house

          3 6 2 nights min

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

          Price per night from

          $258

          Price per night from

          $258

          (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

              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

                24

                NEW! House w/ Kayak - Walk to Stockbridge Bowl!

                Berkshires / Lenox

                Lenox house

                3 6 min stay varies

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

                Price per night from

                $212

                Responds fast!
                avg. 58 minutes

                Price per night from

                $212

                Great rentals within 20 miles that match your search

                Distance approx 13.58 km from Lenox

                  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 8.67 km from Lenox

                    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

                    $345

                    Price per night from

                    $345

                    Distance approx 3.26 km from Lenox 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

                      $288

                      Responds fast!
                      avg. 1 hour 23 minutes

                      Price per night from

                      $288

                      Distance approx 13.83 km from Lenox

                      (3) Very Good 

                        14

                        2200sf Country House on 16 Acres-2 Miles to Jiminy

                        Berkshires / Hancock

                        Hancock house

                        4 9 2 nights min

                        • 4 bedrooms
                        • sleeps 9
                        • 2 nights min
                        • Child Friendly
                        • Pet Friendly
                        “Great house Jiminy Peak” We (family of 4) stayed a weekend in January 2010 with friends (family of 5). It is a great house, perfect location and the owner is really great to deal with. Highly recommended for everyone with kids. easy drive to the slope
                        …see more

                        Price per night from

                        $259

                        Price per night from

                        $259

                        Distance approx 12.29 km from Lenox

                          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 11.83 km from Lenox

                            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 13.99 km from Lenox

                            (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

                              Distance approx 12.25 km from Lenox

                                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 4.42 km from Lenox Show on Map

                                (7) Excellent 

                                  18

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

                                  Berkshires / West Stockbridge

                                  West Stockbridge house

                                  3 8 min stay varies

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

                                  Price per night from

                                  $379

                                  Price per night from

                                  $379

                                  Distance approx 11.69 km from Lenox

                                  (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 11.54 km from Lenox

                                      18

                                      Historic Home on 8.5 Acres

                                      Berkshires / Dalton

                                      Dalton house

                                      3 9 3 nights min

                                      • 3 bedrooms
                                      • sleeps 9
                                      • 3 nights min
                                      • Swimming pool
                                      • Child Friendly
                                      • Air conditioning

                                      Price per night from

                                      $461

                                      Price per night from

                                      $461

                                      Distance approx 11.85 km from Lenox

                                        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 15.61 km from Lenox

                                          7

                                          Berkshires Cottage Country Retreat

                                          New York / Stephentown

                                          Stephentown cottage

                                          3 6 2 nights min

                                          • 3 bedrooms
                                          • sleeps 6
                                          • 2 nights min
                                          • Private garden

                                          Price per night from

                                          $190

                                          Responds fast!
                                          avg. 2 hours 19 minutes

                                          Price per night from

                                          $190

                                          Distance approx 16.41 km from Lenox

                                          (1) Excellent 

                                            21

                                            Berkshire Country Estate - The Library Suite

                                            New York / Old Chatham

                                            Old Chatham house

                                            2 4 2 nights min

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

                                            Price per night from

                                            $173

                                            Price per night from

                                            $173

                                            Distance approx 15.44 km from Lenox

                                              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 5.73 km from Lenox Show on Map

                                                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 5.73 km from Lenox Show on Map

                                                (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 3.54 km from Lenox Show on Map

                                                    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 5.73 km from Lenox Show on Map

                                                    (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 7.14 km from Lenox

                                                        9

                                                        Cedar Chest

                                                        New York / Canaan

                                                        Canaan cottage

                                                        1 2 7 nights min

                                                        • 1 bedroom
                                                        • sleeps 2
                                                        • 7 nights min
                                                        • Beach / lakeside relaxation
                                                        • Nearest beach 2 mi
                                                        • Air conditioning

                                                        Price per night from

                                                        $115

                                                        Price per night from

                                                        $115

                                                        Distance approx 16.41 km from Lenox

                                                          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

                                                          $196

                                                          Price per night from

                                                          $196

                                                          Distance approx 6.63 km from Lenox

                                                            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

                                                            $863

                                                            Price per night from

                                                            $863

                                                            Distance approx 3.76 km from Lenox Show on Map

                                                            (1) Excellent 

                                                              10

                                                              Berkshire House Share-The Blue Room

                                                              Berkshires / Lee

                                                              Lee house

                                                              3 2 1 night min

                                                              • 3 bedrooms
                                                              • sleeps 2
                                                              • 1 night min

                                                              Price per night from

                                                              $87

                                                              Price per night from

                                                              $87

                                                              Distance approx 13.64 km from Lenox

                                                                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

                                                                $517

                                                                Price per night from

                                                                $517

                                                                Distance approx 10.69 km from Lenox

                                                                (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 18.14 km from Lenox

                                                                  (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

                                                                    $576

                                                                    Price per night from

                                                                    $576

                                                                    Distance approx 17.05 km from Lenox

                                                                    (1) Very Good 

                                                                      4

                                                                      Golden Triangle in the Berkshires

                                                                      Berkshires / Hancock

                                                                      Hancock house

                                                                      2 4 2 nights min

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

                                                                      Price per night from

                                                                      $2,873

                                                                      Price per night from

                                                                      $2,873

                                                                      Distance approx 13.63 km from Lenox

                                                                      (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

                                                                        $288

                                                                        Responds fast!
                                                                        avg. 16 minutes

                                                                        Price per night from

                                                                        $288

                                                                        Distance approx 13.23 km from Lenox

                                                                          14

                                                                          Modern Cozy Wooded Retreat

                                                                          New York / Spencertown

                                                                          Spencertown house

                                                                          2 6 30 nights min

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

                                                                          Price per night from

                                                                          $153

                                                                          Price per night from

                                                                          $153

                                                                          Distance approx 9.11 km from Lenox

                                                                            26

                                                                            NEW! Lakefront Berkshires House w/Deck, Dock +Boat

                                                                            Berkshires / Housatonic

                                                                            Housatonic house

                                                                            4 10 min stay varies

                                                                            • 4 bedrooms
                                                                            • sleeps 10
                                                                            • min stay varies
                                                                            • Ski
                                                                            • Child Friendly
                                                                            • Pet Friendly

                                                                            Price per night from

                                                                            $195

                                                                            Responds fast!
                                                                            avg. 21 minutes

                                                                            Price per night from

                                                                            $195

                                                                            Distance approx 7.54 km from Lenox

                                                                            (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

                                                                              $328

                                                                              Price per night from

                                                                              $328