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Filtering by: Tennis in town

26 Houses

    24

    Beautiful Lakefront Berkshire Rental

    Berkshires / Monterey

    Monterey house

    5 6 7 nights min

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

    Price per night from

    $489

    Price per night from

    $489

    Great rentals within 20 miles that match your search

    Distance approx 10.2 km from Monterey

    (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

      $816

      Price per night from

      $816

      Distance approx 4.59 km from Monterey Show on Map

        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

        Distance approx 11.33 km from Monterey

        (1) Excellent 

          24

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

          Berkshires / Stockbridge

          Stockbridge cottage

          2 4 min stay varies

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

          Price per night from

          $320

          Responds fast!
          avg. 12 minutes

          Price per night from

          $320

          Distance approx 7.61 km from Monterey

            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

            $326

            Responds fast!
            avg. 12 minutes

            Price per night from

            $326

            Distance approx 9.81 km from Monterey

              16

              Beautifully Renovated Berkshires Farmhouse

              Berkshires / West Stockbridge

              West Stockbridge b&b

              2 4 2 nights min

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

              Price per night from

              $240

              Price per night from

              $240

              Distance approx 11.96 km from Monterey

              (39) Excellent 

                20

                Berkshire Farmhouse Vacation

                Berkshires / West Stockbridge

                West Stockbridge house

                5 15 min stay varies

                • 5 bedrooms
                • sleeps 15
                • 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

                Price per night from

                $297

                Price per night from

                $297

                Distance approx 11.74 km from Monterey

                (14) Excellent 

                Certificate of Excellence

                  55

                  RiverSong Suite In The Berkshires

                  Berkshires / North Egremont

                  North Egremont apartment

                  1 2 1 night min

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

                  Certificate of Excellence

                  Price per night from

                  $216

                  Responds fast!
                  avg. 11 minutes

                  Price per night from

                  $216

                  Distance approx 9.26 km from Monterey

                  (1) Excellent 

                    10

                    Berkshire House Share-The Blue Room

                    Berkshires / Lee

                    Lee house

                    3 2 1 night min

                    • 3 bedrooms
                    • sleeps 2
                    • 1 night min

                    Price per night from

                    $86

                    Price per night from

                    $86

                    Distance approx 18.14 km from Monterey

                    (8) Excellent 

                      17

                      Outdoor getaway hunting,fishing,skiing..relaxation

                      New York / Copake

                      Copake house

                      3 9 2 nights min

                      • 3 bedrooms
                      • sleeps 9
                      • 2 nights min
                      • Beach / lakeside relaxation
                      • Nearest beach 8 mi
                      • Child Friendly
                      “Home Away from Home ~ A great place to gather11” Had family coming from New York, Massachusetts and Connecticut to celebrate my birthday ~ hotels, motels are expensive, and they're not home. This house offered a great place to convene ~ outdoor gas gr

                      Price per night from

                      $217

                      Price per night from

                      $217

                      Distance approx 9.28 km from Monterey

                        15

                        House share/room for rent

                        Berkshires / Lee

                        Lee private room

                        1 1 1 night min

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

                        Price per night from

                        $77

                        Price per night from

                        $77

                        Distance approx 12.84 km from Monterey

                        (4) Excellent 

                          10

                          Comfortable Farmhouse in the Berkshires

                          Berkshires / West Stockbridge

                          West Stockbridge farmhouse

                          5 12 2 nights min

                          • 5 bedrooms
                          • sleeps 12
                          • 2 nights min
                          • Beach / lakeside relaxation
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $371

                          Responds fast!
                          avg. 3 hours 37 minutes

                          Price per night from

                          $371

                          Distance approx 8.6 km from Monterey

                          (1) Excellent 

                            17

                            Restored 1886 Eyebrow Colonial

                            Berkshires / Stockbridge

                            Stockbridge house

                            2 6 7 nights min

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

                            Price per night from

                            $245

                            Price per night from

                            $245

                            Distance approx 9.09 km from Monterey

                              24

                              Cozy Stockbridge Home - Walk To Golf Course!

                              Berkshires / Stockbridge

                              Stockbridge house

                              2 6 min stay varies

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

                              Price per night from

                              $241

                              Responds fast!
                              avg. 56 minutes

                              Price per night from

                              $241

                              Distance approx 13.35 km from Monterey

                                24

                                Waterfront Home in Tolland w/ Deck - Steps to Lake

                                Connecticut / West Hartland

                                West Hartland log cabin

                                3 8 min stay varies

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

                                Price per night from

                                $264

                                Responds fast!
                                avg. 56 minutes

                                Price per night from

                                $264

                                Distance approx 12.73 km from Monterey

                                  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. 56 minutes

                                  Price per night from

                                  $264

                                  Distance approx 9.18 km from Monterey

                                    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 14.02 km from Monterey

                                    (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

                                      Price per night from

                                      $377

                                      Price per night from

                                      $377

                                      Distance approx 19.35 km from Monterey

                                        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 11.19 km from Monterey

                                          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 13.88 km from Monterey

                                          (1) Excellent 

                                            18

                                            Hillhouse Log Cabin

                                            New York / Hillsdale

                                            Hillsdale log cabin

                                            3 13 2 nights min

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

                                            Price per night from

                                            $487

                                            Price per night from

                                            $487

                                            Distance approx 7.68 km from Monterey

                                              13

                                              Designer Loft Style Residence

                                              Berkshires / Sheffield

                                              Sheffield house

                                              3 6 7 nights min

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

                                              Price per night from

                                              $516

                                              Price per night from

                                              $516

                                              Distance approx 9.75 km from Monterey

                                              (1) Excellent 

                                                20

                                                Newly Renovated Colonial on the River! Sleeps 5-6

                                                Berkshires / Stockbridge

                                                Stockbridge house

                                                3 5 3 nights min

                                                • 3 bedrooms
                                                • sleeps 5
                                                • 3 nights min
                                                • Beach / lakeside relaxation
                                                • Child Friendly

                                                Price per night from

                                                $327

                                                Price per night from

                                                $327

                                                Distance approx 8.62 km from Monterey

                                                (5) Excellent 

                                                  10

                                                  Apple Cottage

                                                  Berkshires / Sheffield

                                                  Sheffield farmhouse

                                                  3 8 1 night min

                                                  • 3 bedrooms
                                                  • sleeps 8
                                                  • 1 night min
                                                  • Ask about children
                                                  • Air conditioning
                                                  • Private garden

                                                  Price per night from

                                                  $430

                                                  Responds fast!
                                                  avg. 3 hours 22 minutes

                                                  Price per night from

                                                  $430

                                                  Distance approx 10.09 km from Monterey

                                                    31

                                                    |The Escape |STOCKBRIDGE| NEW Home |BERKSHIRES|

                                                    Berkshires / Stockbridge

                                                    Stockbridge house

                                                    4 9 min stay varies

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

                                                    Price per night from

                                                    $516

                                                    Responds fast!
                                                    avg. 1 hour 21 minutes

                                                    Price per night from

                                                    $516

                                                    Distance approx 11.4 km from Monterey

                                                    (6) Excellent 

                                                      16

                                                      Family-friendly Cottage Near Lake, Tanglewood

                                                      Berkshires / Stockbridge

                                                      Stockbridge cottage

                                                      3 7 2 nights min

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

                                                      Price per night from

                                                      $327

                                                      Price per night from

                                                      $327