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Filtering by: Walking trips

42 Houses

    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

    $344

    Responds fast!
    avg. 21 minutes

    Price per night from

    $344

      25

      NEW! Monterey Home w/Porch by Beach & State Parks!

      Berkshires / Monterey

      Monterey house

      3 7 min stay varies

      • 3 bedrooms
      • sleeps 7
      • min stay varies
      • Ski
      • Child Friendly
      • Pet Friendly

      Price per night from

      $229

      Responds fast!
      avg. 21 minutes

      Price per night from

      $229

        24

        NEW-Pet-Friendly Berkshires Home w/Dock & Fire Pit

        Berkshires / Monterey

        Monterey house

        3 10 7 nights min

        • 3 bedrooms
        • sleeps 10
        • 7 nights min
        • Child Friendly
        • Pet Friendly

        Price per night from

        $212

        Responds fast!
        avg. 21 minutes

        Price per night from

        $212

        Great rentals within 20 miles that match your search

        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

          $263

          Responds fast!
          avg. 30 minutes

          Price per night from

          $263

          Distance approx 9.46 km from Monterey

            6

            Stunning Home! 120 Acres! Amazing!

            Berkshires / Great Barrington

            Great Barrington house

            9 16 3 nights min

            • 9 bedrooms
            • sleeps 16
            • 3 nights min
            • Swimming pool
            • Child Friendly
            • Air conditioning

            Price per night from

            $4,113

            Price per night from

            $4,113

            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

              $376

              Price per night from

              $376

              Distance approx 8.76 km from Monterey

                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. 21 minutes

                Price per night from

                $275

                Distance approx 16.38 km from Monterey

                  25

                  Historic Huntington Home - Walk to Westfield River

                  Hampshire County / Huntington

                  Huntington house

                  3 7 min stay varies

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

                  Price per night from

                  $218

                  Responds fast!
                  avg. 21 minutes

                  Price per night from

                  $218

                  Distance approx 10.3 km from Monterey

                    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

                    $212

                    Responds fast!
                    avg. 21 minutes

                    Price per night from

                    $212

                    Distance approx 4.01 km from Monterey

                    (1) Excellent 

                      50

                      Berkshire Getaway Home with Lake Access

                      Berkshires / Otis

                      Otis house

                      4 10 2 nights min

                      • 4 bedrooms
                      • sleeps 10
                      • 2 nights min
                      • Child Friendly

                      Price per night from

                      $453

                      Responds fast!
                      avg. 3 hours 4 minutes

                      Price per night from

                      $453

                      Distance approx 8.24 km from Monterey

                        30

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

                        Berkshires / Becket

                        Becket house

                        3 8 min stay varies

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

                        Price per night from

                        $373

                        Responds fast!
                        avg. 21 minutes

                        Price per night from

                        $373

                        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 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 3.49 km from Monterey Show on Map

                            (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

                              $206

                              Responds fast!
                              avg. 21 minutes

                              Price per night from

                              $206

                              Distance approx 8.87 km from Monterey

                              (1) Excellent 

                                14

                                The perfect Southern Berkshire winter vacation esc

                                Berkshires / Sheffield

                                Sheffield house

                                4 10 7 nights min

                                • 4 bedrooms
                                • sleeps 10
                                • 7 nights min
                                • Swimming pool
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $573

                                Price per night from

                                $573

                                Distance approx 12.13 km from Monterey

                                (1) Excellent 

                                  24

                                  'Butterfly Hill' West Stockbridge Home on 3 Acres!

                                  Berkshires / West Stockbridge

                                  West Stockbridge house

                                  2 4 min stay varies

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

                                  Price per night from

                                  $189

                                  Responds fast!
                                  avg. 21 minutes

                                  Price per night from

                                  $189

                                  Distance approx 16.22 km from Monterey

                                    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

                                    $1,374

                                    Price per night from

                                    $1,374

                                    Distance approx 11.41 km from Monterey

                                      24

                                      Berkshires Home 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. 2 hours 43 minutes

                                      Price per night from

                                      $212

                                      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 19.88 km from Monterey

                                          26

                                          NEW! Charming Berkshires Cottage on Ashmere Lake

                                          Berkshires / Hinsdale

                                          Hinsdale cottage

                                          3 6 3 nights min

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

                                          Price per night from

                                          $224

                                          Responds fast!
                                          avg. 17 minutes

                                          Price per night from

                                          $224

                                          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 10.19 km from Monterey

                                            (4) Very Good 

                                              18

                                              Lakefront Berkshires Ski/Summer House, Great Views

                                              Berkshires / Great Barrington

                                              Great Barrington house

                                              4 10 min stay varies

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

                                              Price per night from

                                              $216

                                              Price per night from

                                              $216

                                              Distance approx 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 18.3 km from Monterey

                                                  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 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 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 16.07 km from Monterey

                                                      (3) Excellent 

                                                        11

                                                        Overnight at Althouse -Higgins

                                                        New York / Hillsdale

                                                        Hillsdale apartment

                                                        2 4 2 nights min

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

                                                        Price per night from

                                                        $201

                                                        Price per night from

                                                        $201

                                                        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. 7 minutes

                                                          Price per night from

                                                          $264

                                                          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

                                                            $241

                                                            Price per night from

                                                            $241

                                                            Distance approx 5.16 km from Monterey

                                                            (1) Average 

                                                              15

                                                              Charming and Spacious Colonial Farmhouse on 4 Acre Estate

                                                              Berkshires / Tyringham

                                                              Tyringham villa

                                                              4 8 2 nights min

                                                              • 4 bedrooms
                                                              • sleeps 8
                                                              • 2 nights min
                                                              • Beach / lakeside relaxation
                                                              • Nearest beach 2 mi
                                                              • Child Friendly

                                                              Price per night from

                                                              $453

                                                              Responds fast!
                                                              avg. 1 hour 37 minutes

                                                              Price per night from

                                                              $453

                                                              Distance approx 5.33 km from Monterey

                                                                35

                                                                Charming Private Guest Suite in Historic Village in the Berkshires

                                                                Berkshires / New Marlborough

                                                                New Marlborough studio

                                                                Studio 2 1 night min

                                                                • Studio
                                                                • sleeps 2
                                                                • 1 night min

                                                                Price per night from

                                                                $109

                                                                Price per night from

                                                                $109

                                                                Distance approx 16.45 km from Monterey

                                                                  11

                                                                  Beautiful Cottage at the foot of the Berkshires

                                                                  New York / Copake Falls

                                                                  Copake Falls cottage

                                                                  2 4 2 nights min

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

                                                                  Price per night from

                                                                  $201

                                                                  Price per night from

                                                                  $201

                                                                  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 3.48 km from Monterey Show on Map

                                                                      24

                                                                      Rustic Berkshires Cottage w/ Views of Lake Buel!

                                                                      Berkshires / New Marlborough

                                                                      New Marlborough cottage

                                                                      1 2 7 nights min

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

                                                                      Price per night from

                                                                      $126

                                                                      Responds fast!
                                                                      avg. 7 minutes

                                                                      Price per night from

                                                                      $126

                                                                      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

                                                                        $217

                                                                        Responds fast!
                                                                        avg. 11 minutes

                                                                        Price per night from

                                                                        $217

                                                                        Distance approx 10.58 km from Monterey

                                                                          36

                                                                          Spacious Berkshires Home w/ Pool & Patio!

                                                                          Berkshires / North Egremont

                                                                          North Egremont house

                                                                          5 10 2 nights min

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

                                                                          Price per night from

                                                                          $859

                                                                          Responds fast!
                                                                          avg. 7 minutes

                                                                          Price per night from

                                                                          $859

                                                                          Distance approx 16.81 km from Monterey

                                                                          (4) Excellent 

                                                                            10

                                                                            Great Vacation House in the Berkshires by Richmond Pond

                                                                            Berkshires / Richmond

                                                                            Richmond house

                                                                            2 6 7 nights min

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

                                                                            Price per night from

                                                                            $213

                                                                            Price per night from

                                                                            $213

                                                                            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. 7 minutes

                                                                              Price per night from

                                                                              $241