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140 Houses

    58

    Country estate on 100 acres perfect for families

    New York / Chatham

    Chatham house

    4 6 7 nights min

    • 4 bedrooms
    • sleeps 6
    • 7 nights min
    • Child Friendly

    Price per night from

    $1,145

    Price per night from

    $1,145

    Great rentals within 20 miles that match your search

    Distance approx 14.59 km from Chatham

    (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

      $214

      Price per night from

      $214

      Distance approx 8.07 km from Chatham

        28

        Country Retreat w/ Pool Near Hip Hudson, NY

        New York / Hudson

        Hudson house

        3 8 3 nights min

        • 3 bedrooms
        • sleeps 8
        • 3 nights min
        • Swimming pool
        • Child Friendly
        • Ask about pets

        Price per night from

        $461

        Price per night from

        $461

        Distance approx 14.57 km from Chatham

        (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
          …see more

          Price per night from

          $229

          Price per night from

          $229

          Distance approx 7.32 km from Chatham Show on Map

            29

            Beauty in the Berkshires

            New York / Austerlitz

            Austerlitz house

            6 14 2 nights min

            • 6 bedrooms
            • sleeps 14
            • 2 nights min
            • Child Friendly

            Price per night from

            $1,381

            Price per night from

            $1,381

            Distance approx 15.12 km from Chatham

            (3) Very Good 

              54

              OUR LOVELY VACATION HOME IS LOCATED IN THE CATSKIL

              Catskill Region / Catskill

              Catskill finca

              4 10 1 night min

              • 4 bedrooms
              • sleeps 10
              • 1 night min
              • Beach / lakeside relaxation
              • Swimming pool
              • Child Friendly

              Price per night from

              $403

              Responds fast!
              avg. 3 hours 40 minutes

              Price per night from

              $403

              Distance approx 19.74 km from Chatham

                30

                Evergreen Pines Country Estate Villa

                New York / Ancram

                Ancram house

                4 8 1 night min

                • 4 bedrooms
                • sleeps 8
                • 1 night min
                • Beach / lakeside relaxation
                • Swimming pool
                • Child Friendly

                Price per night from

                $2,298

                Price per night from

                $2,298

                Distance approx 14.24 km from Chatham

                  16

                  Escape to Avalon Cottage in the Hudson Valley

                  New York / Craryville

                  Craryville house

                  3 5 3 nights min

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

                  Price per night from

                  $167

                  Price per night from

                  $167

                  Distance approx 17.35 km from Chatham

                  (1) Excellent 

                    10

                    Cabin on the Poetic Creek

                    New York / Leeds

                    Leeds log cabin

                    1 4 1 night min

                    • 1 bedroom
                    • sleeps 4
                    • 1 night min
                    • Child Friendly
                    • Pet Friendly

                    Price per night from

                    $156

                    Responds fast!
                    avg. 3 hours 6 minutes

                    Price per night from

                    $156

                    Distance approx 16.66 km from Chatham

                    (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
                      …see more

                      Price per night from

                      $219

                      Price per night from

                      $219

                      Distance approx 11.61 km from Chatham

                      (7) Excellent 

                        18

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

                        Berkshires / West Stockbridge

                        West Stockbridge house

                        3 8 min stay varies

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

                        Price per night from

                        $379

                        Price per night from

                        $379

                        Distance approx 16.7 km from Chatham

                        (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

                          $230

                          Responds fast!
                          avg. 2 hours 41 minutes

                          Price per night from

                          $230

                          Distance approx 16.81 km from Chatham

                            36

                            Spacious Berkshires Home w/ Pool & Patio!

                            Berkshires / North Egremont

                            North Egremont house

                            5 10 2 nights min

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

                            Price per night from

                            $858

                            Responds fast!
                            avg. 9 minutes

                            Price per night from

                            $858

                            Distance approx 11.51 km from Chatham

                              16

                              Olde York Farm Distillery Suite

                              New York / Claverack

                              Claverack farmhouse

                              2 6 1 night min

                              • 2 bedrooms
                              • sleeps 6
                              • 1 night min
                              • Beach / lakeside relaxation
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $286

                              Price per night from

                              $286

                              Distance approx 16.27 km from Chatham

                              (4) Excellent 

                                30

                                Gem of the Berkshires, walk to downtown & lake.

                                Berkshires / Great Barrington

                                Great Barrington house

                                5 12 2 nights min

                                • 5 bedrooms
                                • sleeps 12
                                • 2 nights min
                                • Nearest beach 0.32 mi
                                • Child Friendly
                                • Air conditioning
                                “Wonderful Home!” We had a wonderful weekend! The home and area are lovely - easy walk to town for drinks and dinner - and enjoyed sitting on the many porches, looking out at the view. The home has been upgraded and the kitchen and living areas are b
                                …see more

                                Price per night from

                                $345

                                Price per night from

                                $345

                                Distance approx 7.9 km from Chatham Show on Map

                                  48

                                  Total Privacy! Tanglewood Retreat With Berkshire Views!

                                  New York / Hillsdale

                                  Hillsdale house

                                  5 14 2 nights min

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

                                  Price per night from

                                  $691

                                  Price per night from

                                  $691

                                  Distance approx 8.77 km from Chatham

                                    19

                                    Relaxing Victorian Farmhouse

                                    New York / Philmont

                                    Philmont house

                                    3 4 2 nights min

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

                                    Price per night from

                                    $225

                                    Price per night from

                                    $225

                                    Distance approx 13.41 km from Chatham

                                    (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

                                      $218

                                      Responds fast!
                                      avg. 33 minutes

                                      Price per night from

                                      $218

                                      Distance approx 12.16 km from Chatham

                                      (39) Excellent 

                                        20

                                        Berkshire Farmhouse Vacation

                                        Berkshires / West Stockbridge

                                        West Stockbridge house

                                        5 12 min stay varies

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

                                        Price per night from

                                        $300

                                        Price per night from

                                        $300

                                        Distance approx 15.51 km from Chatham

                                          15

                                          S. Berkshires Mountain Treehouse • Views • Privacy

                                          Berkshires / Great Barrington

                                          Great Barrington house

                                          2 4 14 nights min

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

                                          Price per night from

                                          $214

                                          Responds fast!
                                          avg. 1 hour 16 minutes

                                          Price per night from

                                          $214

                                          Distance approx 12.62 km from Chatham

                                          (1) Excellent 

                                            9

                                            The Artist's House - Special Winter Rates!

                                            New York / Hudson

                                            Hudson house

                                            3 6 2 nights min

                                            • 3 bedrooms
                                            • sleeps 6
                                            • 2 nights min
                                            • Car not necessary
                                            • Air conditioning
                                            • Private garden

                                            Price per night from

                                            $403

                                            Price per night from

                                            $403

                                            Distance approx 18.61 km from Chatham

                                              13

                                              Berkshires Summer Rental Beaver Pond Hancock MA

                                              Berkshires / Hancock

                                              Hancock condo

                                              3 6 30 nights min

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

                                              Price per night from

                                              $115

                                              Price per night from

                                              $115

                                              Distance approx 13.21 km from Chatham

                                              (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

                                                $202

                                                Price per night from

                                                $202

                                                Distance approx 14.17 km from Chatham

                                                  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

                                                  $805

                                                  Price per night from

                                                  $805

                                                  Distance approx 12.36 km from Chatham

                                                    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 17.99 km from Chatham

                                                      13

                                                      Garfield House

                                                      Maine / Lee

                                                      Lee apartment

                                                      2 6 2 nights min

                                                      • 2 bedrooms
                                                      • sleeps 6
                                                      • 2 nights min
                                                      • Child Friendly
                                                      • Pet Friendly

                                                      Price per night from

                                                      $201

                                                      Price per night from

                                                      $201

                                                      Distance approx 3.74 km from Chatham Show on Map

                                                        19

                                                        Berkshire Country Estate - Rose Suite

                                                        New York / Old Chatham

                                                        Old Chatham villa

                                                        2 4 2 nights min

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

                                                        Price per night from

                                                        $196

                                                        Price per night from

                                                        $196

                                                        Distance approx 9.67 km from Chatham Show on Map

                                                          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 9.14 km from Chatham

                                                            10

                                                            Red Mapple Farm

                                                            New York / Malden Bridge

                                                            Malden Bridge house

                                                            4 8 4 nights min

                                                            • 4 bedrooms
                                                            • sleeps 8
                                                            • 4 nights min
                                                            • Ski
                                                            • Child Friendly

                                                            Price per night from

                                                            $507

                                                            Price per night from

                                                            $507

                                                            Distance approx 12.59 km from Chatham

                                                              20

                                                              Blue SKies

                                                              New York / Hudson

                                                              Hudson apartment

                                                              3 7 2 nights min

                                                              • 3 bedrooms
                                                              • sleeps 7
                                                              • 2 nights min
                                                              • Child Friendly

                                                              Price per night from

                                                              $288

                                                              Price per night from

                                                              $288

                                                              Distance approx 14.43 km from Chatham

                                                                10

                                                                The Barn at Copake Lake

                                                                New York / Craryville

                                                                Craryville barn

                                                                3 14 2 nights min

                                                                • 3 bedrooms
                                                                • sleeps 14
                                                                • 2 nights min
                                                                • Child Friendly

                                                                Price per night from

                                                                $689

                                                                Price per night from

                                                                $689

                                                                Distance approx 19.06 km from Chatham

                                                                  26

                                                                  Catskill village/Hudson retreat

                                                                  New York / Freehold

                                                                  Freehold farmhouse

                                                                  3 6 2 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 6
                                                                  • 2 nights min
                                                                  • Ski
                                                                  • Suitable for children age 5+
                                                                  • Private garden

                                                                  Price per night from

                                                                  $311

                                                                  Price per night from

                                                                  $311

                                                                  Distance approx 13.04 km from Chatham

                                                                    26

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

                                                                    Berkshires / Housatonic

                                                                    Housatonic house

                                                                    4 10 min stay varies

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

                                                                    Price per night from

                                                                    $195

                                                                    Responds fast!
                                                                    avg. 21 minutes

                                                                    Price per night from

                                                                    $195

                                                                    Distance approx 4.03 km from Chatham Show on Map

                                                                      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 16.36 km from Chatham

                                                                        18

                                                                        3 Bedroom Hudson Valley Farm House

                                                                        New York / Craryville

                                                                        Craryville guest house

                                                                        3 6 2 nights min

                                                                        • 3 bedrooms
                                                                        • sleeps 6
                                                                        • 2 nights min
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $368

                                                                        Price per night from

                                                                        $368

                                                                        Distance approx 12.2 km from Chatham

                                                                          33

                                                                          Palazzo Hudson: a light filled home

                                                                          New York / Hudson

                                                                          Hudson house

                                                                          3 7 2 nights min

                                                                          • 3 bedrooms
                                                                          • sleeps 7
                                                                          • 2 nights min

                                                                          Price per night from

                                                                          $277

                                                                          Price per night from

                                                                          $277

                                                                          Distance approx 13.61 km from Chatham

                                                                          (1) Excellent 

                                                                            20

                                                                            Newly Renovated Colonial on the River! Sleeps 5-6

                                                                            Berkshires / Stockbridge

                                                                            Stockbridge house

                                                                            3 5 3 nights min

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

                                                                            Price per night from

                                                                            $328

                                                                            Price per night from

                                                                            $328

                                                                            Distance approx 13.32 km from Chatham

                                                                              13

                                                                              Double Room in Historic Farmhouse

                                                                              New York / West Coxsackie

                                                                              West Coxsackie b and b

                                                                              1 2 1 night min

                                                                              • 1 bedroom
                                                                              • sleeps 2
                                                                              • 1 night min
                                                                              • Child Friendly
                                                                              • Ask about pets

                                                                              Price per night from

                                                                              $115

                                                                              Price per night from

                                                                              $115