Monterey Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

Filtering by: Garden

53 Houses

    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

    $457

    Responds fast!
    avg. 3 hours 40 minutes

    Price per night from

    $457

    Great rentals within 20 miles that match your search

    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

      $215

      Responds fast!
      avg. 11 minutes

      Price per night from

      $215

      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 9.79 km from Monterey

        (24) Excellent 

          18

          Berkshires: Romantic Cottage with spectacular view

          Berkshires / Great Barrington

          Great Barrington cottage

          1 3 min stay varies

          • 1 bedroom
          • sleeps 3
          • min stay varies
          • Nearest beach 2 mi
          • Swimming pool
          • Ask about children
          “Perhaps the most relaxing vacation I've ever had” The Sigels' cottage was absolutely perfect for us. My husband and I were looking for a nice quiet 4-night stay while our 7-yr-old twins visited with their grandparents. When we arrived everything loo

          Price per night from

          $228

          Price per night from

          $228

          Distance approx 12.73 km from Monterey

          (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,

            Price per night from

            $229

            Price per night from

            $229

            Distance approx 18.08 km from Monterey

            (2) Excellent 

              14

              Newly Renovated Lakefront Getaway on Robinson Pond

              New York / Copake

              Copake house

              3 5 3 nights min

              • 3 bedrooms
              • sleeps 5
              • 3 nights min
              • Beach / lakeside relaxation
              • Nearest beach 0 mi
              • Child Friendly

              Price per night from

              $229

              Responds fast!
              avg. 1 hour 58 minutes

              Price per night from

              $229

              Distance approx 16.87 km from Monterey

              (20) Excellent 

                18

                The Cottage at Great Falls

                Connecticut / Falls Village

                Falls Village cottage

                2 4 2 nights min

                • 2 bedrooms
                • sleeps 4
                • 2 nights min
                “Relaxation Overload” Went with the girlfriend for a weekend getaway and chose the perfect place. Extremely relaxing and soothing trip. Everything you need is there, french press? Yep. Towels? Yep. Amazing art? Yep! This place is incredibly decorated a

                Price per night from

                $275

                Responds fast!
                avg. 1 hour 42 minutes

                Price per night from

                $275

                Distance approx 7.91 km from Monterey

                (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

                  Price per night from

                  $343

                  Price per night from

                  $343

                  Distance approx 9.13 km from Monterey

                    21

                    Private Berkshire Estate w/Pool & Tennis Court

                    Berkshires / Great Barrington

                    Great Barrington house

                    4 12 min stay varies

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

                    Price per night from

                    $657

                    Price per night from

                    $657

                    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

                      $215

                      Price per night from

                      $215

                      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

                        $486

                        Price per night from

                        $486

                        Distance approx 10.1 km from Monterey

                        (1) Excellent 

                          13

                          The Gatehouse on Golden Hill

                          Berkshires / Lee

                          Lee house

                          4 14 3 nights min

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

                          Price per night from

                          $913

                          Price per night from

                          $913

                          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

                            $514

                            Responds fast!
                            avg. 1 hour 21 minutes

                            Price per night from

                            $514

                            Distance approx 12.67 km from Monterey

                            (1) Excellent 

                              22

                              Berkshire Getaway at 'Tofu'S Retreat'

                              Berkshires / Alford

                              Alford chateau

                              3 6 7 nights min

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

                              Price per night from

                              $246

                              Responds fast!
                              avg. 1 hour 31 minutes

                              Price per night from

                              $246

                              Distance approx 9.62 km from Monterey

                              (13) Excellent 

                                17

                                Serene Lakefront Cottage

                                Berkshires / Becket

                                Becket house

                                2 6 min stay varies

                                • 2 bedrooms
                                • sleeps 6
                                • min stay varies
                                • Child Friendly
                                • Air conditioning
                                • Pet Friendly
                                “Peaceful country escape” Really enjoyed the stay here. Very complete driving and house directions provided by the owners, and checking in - even at a late hour - was a breeze. The house was very clean, woods and lake were beautiful. Many of the hou

                                Price per night from

                                $171

                                Price per night from

                                $171

                                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 16.81 km from Monterey

                                  (4) Excellent 

                                    10

                                    Great Vacation House in the Berkshires by Richmond Pond

                                    Berkshires / Richmond

                                    Richmond house

                                    2 6 min stay varies

                                    • 2 bedrooms
                                    • sleeps 6
                                    • min stay varies
                                    • Beach / lakeside relaxation
                                    • Child Friendly
                                    • Air conditioning

                                    Price per night from

                                    $213

                                    Price per night from

                                    $213

                                    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

                                      $452

                                      Responds fast!
                                      avg. 1 hour 37 minutes

                                      Price per night from

                                      $452

                                      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 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 12.88 km from Monterey

                                          (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

                                            $200

                                            Responds fast!
                                            avg. 1 hour 58 minutes

                                            Price per night from

                                            $200

                                            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 15.86 km from Monterey

                                              (1) Excellent 

                                                34

                                                INTERIOR DESIGNERS BOTANICAL COTTAGE

                                                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

                                                $166

                                                Price per night from

                                                $166

                                                Distance approx 14.37 km from Monterey

                                                  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 5.23 km from Monterey

                                                  (1) Excellent 

                                                    10

                                                    Romantic Berkshire Cottage on Storybook Estate

                                                    Berkshires / Tyringham

                                                    Tyringham cottage

                                                    1 2 2 nights min

                                                    • 1 bedroom
                                                    • sleeps 2
                                                    • 2 nights min
                                                    • Ask about children
                                                    • Pet Friendly

                                                    Price per night from

                                                    $258

                                                    Responds fast!
                                                    avg. 1 hour 37 minutes

                                                    Price per night from

                                                    $258

                                                    Distance approx 7.73 km from Monterey

                                                      4

                                                      Just the Spot! Cozy home by the Lake...

                                                      Berkshires / Great Barrington

                                                      Great Barrington house

                                                      3 7 2 nights min

                                                      • 3 bedrooms
                                                      • sleeps 7
                                                      • 2 nights min
                                                      • Child Friendly
                                                      • Pet Friendly
                                                      • Private garden

                                                      Price per night from

                                                      $201

                                                      Price per night from

                                                      $201

                                                      Distance approx 11.38 km from Monterey

                                                      (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

                                                        Distance approx 10.7 km from Monterey

                                                          4

                                                          Nasturtium Room

                                                          Berkshires / Stockbridge

                                                          Stockbridge farmhouse

                                                          1 3 1 night min

                                                          • 1 bedroom
                                                          • sleeps 3
                                                          • 1 night min
                                                          • Child Friendly
                                                          • Pet Friendly
                                                          • Private garden

                                                          Price per night from

                                                          $172

                                                          Price per night from

                                                          $172

                                                          Distance approx 8.5 km from Monterey

                                                          (2) Excellent 

                                                            22

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

                                                            Berkshires / Lee

                                                            Lee house

                                                            5 30 min stay varies

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

                                                            Price per night from

                                                            $915

                                                            Responds fast!
                                                            avg. 1 hour 36 minutes

                                                            Price per night from

                                                            $915

                                                            Distance approx 15.83 km from Monterey

                                                              12

                                                              Colebrook Dream

                                                              Connecticut / Colebrook

                                                              Colebrook house

                                                              3 12 2 nights min

                                                              • 3 bedrooms
                                                              • sleeps 12
                                                              • 2 nights min
                                                              • Child Friendly
                                                              • Air conditioning
                                                              • Private garden

                                                              Price per night from

                                                              $344

                                                              Price per night from

                                                              $344

                                                              Distance approx 4.77 km from Monterey

                                                                10

                                                                Country Victorian Serenity in the Berkshires

                                                                Berkshires / New Marlborough

                                                                New Marlborough house

                                                                4 6 7 nights min

                                                                • 4 bedrooms
                                                                • sleeps 6
                                                                • 7 nights min
                                                                • Suitable for children age 5+
                                                                • Private garden

                                                                Price per night from

                                                                $263

                                                                Price per night from

                                                                $263

                                                                Distance approx 7.87 km from Monterey

                                                                  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 17.87 km from Monterey

                                                                  (1) Excellent 

                                                                    11

                                                                    Riverwood - Cozy Carriage House in the Woods

                                                                    Connecticut / Falls Village

                                                                    Falls Village apartment

                                                                    1 2 2 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 2
                                                                    • 2 nights min
                                                                    • Ask about children
                                                                    • Air conditioning
                                                                    • Private garden

                                                                    Price per night from

                                                                    $258

                                                                    Price per night from

                                                                    $258

                                                                    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 9.95 km from Monterey

                                                                        12

                                                                        Fabulous NEW Spacious House in the Berkshires Tanglewood

                                                                        Berkshires / Stockbridge

                                                                        Stockbridge house

                                                                        4 8 min stay varies

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

                                                                        Price per night from

                                                                        $287

                                                                        Responds fast!
                                                                        avg. 2 hours 1 minutes

                                                                        Price per night from

                                                                        $287

                                                                        Distance approx 7.84 km from Monterey

                                                                        (2) Average 

                                                                          27

                                                                          Shaker Hill

                                                                          Berkshires / Great Barrington

                                                                          Great Barrington house

                                                                          5 10 3 nights min

                                                                          • 5 bedrooms
                                                                          • sleeps 10
                                                                          • 3 nights min
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $430

                                                                          Price per night from

                                                                          $430

                                                                          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

                                                                            $218

                                                                            Price per night from

                                                                            $218

                                                                            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