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140 Houses

    19

    Relax Like Royalty in Your Own Castle!

    New York / Ghent

    Ghent house

    2 4 1 night min

    • 2 bedrooms
    • sleeps 4
    • 1 night min
    • Beach / lakeside relaxation
    • Ask about children
    • Air conditioning

    Price per night from

    $343

    Price per night from

    $343

    (1) Excellent 

      13

      Hudson Valley Cottage

      New York / Ghent

      Ghent cottage

      1 4 1 night min

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

      Price per night from

      $172

      Price per night from

      $172

      Great rentals within 20 miles that match your search

      Distance approx 6.25 km from Ghent

        18

        Mountain Views Atop Blueberry Hill on 40 Acres

        New York / Austerlitz

        Austerlitz house

        3 6 2 nights min

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

        Price per night from

        $230

        Price per night from

        $230

        Distance approx 15.79 km from Ghent

        (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

          $244

          Price per night from

          $244

          Distance approx 18.4 km from Ghent

            23

            The Dacha: Summer/Skiing House in the Berkshires

            New York / Treadwell

            Treadwell apartment

            2 6 3 nights min

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

            Price per night from

            $264

            Price per night from

            $264

            Distance approx 14.03 km from Ghent

            (2) Excellent 

              24

              Country Elegance in the Berkshires

              Berkshires / Great Barrington

              Great Barrington house

              4 12 2 nights min

              • 4 bedrooms
              • sleeps 12
              • 2 nights min
              • Nearest beach 0 mi
              • Child Friendly
              • Air conditioning

              Price per night from

              $746

              Responds fast!
              avg. 2 hours 46 minutes

              Price per night from

              $746

              Distance approx 4.58 km from Ghent

                8

                mile hill b and b

                New York / Kinderhook

                Kinderhook house

                2 4 1 night min

                • 2 bedrooms
                • sleeps 4
                • 1 night min
                • Swimming pool
                • Child Friendly
                • Air conditioning

                Price per night from

                $212

                Price per night from

                $212

                Distance approx 13.72 km from Ghent

                (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 17.45 km from Ghent

                    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

                    $2,293

                    Price per night from

                    $2,293

                    Distance approx 12.32 km from Ghent

                    (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. 33 minutes

                      Price per night from

                      $217

                      Distance approx 19.76 km from Ghent

                        12

                        Fabulous Post & Beam Berkshire Rental

                        Berkshires / Monterey

                        Monterey house

                        7 21 nights min

                        • sleeps 7
                        • 21 nights min
                        • Ask about children
                        • Car not necessary
                        • Ask about pets

                        Price per night from

                        $204

                        Price per night from

                        $204

                        Distance approx 5.98 km from Ghent

                          24

                          Beautiful Berkshire Country Estate

                          New York / Old Chatham

                          Old Chatham house

                          8 16 min stay varies

                          • 8 bedrooms
                          • sleeps 16
                          • min stay varies
                          • Swimming pool
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $1,032

                          Price per night from

                          $1,032

                          Distance approx 12.44 km from Ghent

                          (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

                            $378

                            Price per night from

                            $378

                            Distance approx 14.63 km from Ghent

                            (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

                              $218

                              Price per night from

                              $218

                              Distance approx 5.84 km from Ghent

                                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

                                $459

                                Price per night from

                                $459

                                Distance approx 19.01 km from Ghent

                                (2) Very Good 

                                  12

                                  Berkshires Spacious Comfortable Charming Farmhouse

                                  Berkshires / Lee

                                  Lee apartment

                                  3 8 2 nights min

                                  • 3 bedrooms
                                  • sleeps 8
                                  • 2 nights min
                                  • Child Friendly
                                  • Air conditioning
                                  “lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.
                                  …see more

                                  Price per night from

                                  $344

                                  Responds fast!
                                  avg. 1 hour 42 minutes

                                  Price per night from

                                  $344

                                  Distance approx 9.22 km from Ghent

                                    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

                                    $285

                                    Price per night from

                                    $285

                                    Distance approx 15.54 km from Ghent

                                      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

                                      $855

                                      Responds fast!
                                      avg. 9 minutes

                                      Price per night from

                                      $855

                                      Distance approx 12.32 km from Ghent

                                        32

                                        RIVERSONG "PENTHOUSE"

                                        Berkshires / North Egremont

                                        North Egremont room

                                        1 2 1 night min

                                        • 1 bedroom
                                        • sleeps 2
                                        • 1 night min
                                        • Air conditioning
                                        • Private garden

                                        Price per night from

                                        $171

                                        Responds fast!
                                        avg. 33 minutes

                                        Price per night from

                                        $171

                                        Distance approx 19.15 km from Ghent

                                          7

                                          Berkshires Cottage Country Retreat

                                          New York / Stephentown

                                          Stephentown cottage

                                          3 6 2 nights min

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

                                          Price per night from

                                          $190

                                          Responds fast!
                                          avg. 2 hours 19 minutes

                                          Price per night from

                                          $190

                                          Distance approx 13.94 km from Ghent

                                            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

                                            $212

                                            Responds fast!
                                            avg. 1 hour 16 minutes

                                            Price per night from

                                            $212

                                            Distance approx 14.76 km from Ghent

                                              24

                                              Peaceful 5BR Nassau Duplex w/ Beautiful Lawn

                                              New York / Nassau

                                              Nassau house

                                              5 16 2 nights min

                                              • 5 bedrooms
                                              • sleeps 16
                                              • 2 nights min
                                              • Ski
                                              • Child Friendly
                                              • Air conditioning

                                              Price per night from

                                              $129

                                              Responds fast!
                                              avg. 9 minutes

                                              Price per night from

                                              $129

                                              Distance approx 14.64 km from Ghent

                                                22

                                                Vacation Home on 10 Acres with Pool and Spa

                                                Berkshires / Stockbridge

                                                Stockbridge house

                                                3 6 7 nights min

                                                • 3 bedrooms
                                                • sleeps 6
                                                • 7 nights min
                                                • Child Friendly
                                                • Ask about pets

                                                Price per night from

                                                $860

                                                Price per night from

                                                $860

                                                Distance approx 13.34 km from Ghent

                                                  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

                                                  $570

                                                  Price per night from

                                                  $570

                                                  Distance approx 16.92 km from Ghent

                                                    23

                                                    Renovated 2 bedroom in Heart of Lenox

                                                    Berkshires / Lenox

                                                    Lenox apartment

                                                    2 4 1 night min

                                                    • 2 bedrooms
                                                    • sleeps 4
                                                    • 1 night min
                                                    • Child Friendly
                                                    • Air conditioning

                                                    Price per night from

                                                    $344

                                                    Price per night from

                                                    $344

                                                    Distance approx 18.51 km from Ghent

                                                      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

                                                      $200

                                                      Price per night from

                                                      $200

                                                      Distance approx 11.2 km from Ghent

                                                        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 14.37 km from Ghent

                                                        (1) Very Good 

                                                          14

                                                          Cozy and clean in Gt Barrington- available for October

                                                          Berkshires / Great Barrington

                                                          Great Barrington house

                                                          2 4 3 nights min

                                                          • 2 bedrooms
                                                          • sleeps 4
                                                          • 3 nights min
                                                          • Nearest beach 2 mi
                                                          • Child Friendly
                                                          • Pet Friendly

                                                          Price per night from

                                                          $172

                                                          Responds fast!
                                                          avg. 3 hours 37 minutes

                                                          Price per night from

                                                          $172

                                                          Distance approx 10.3 km from Ghent

                                                          (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

                                                            $247

                                                            Responds fast!
                                                            avg. 1 hour 10 minutes

                                                            Price per night from

                                                            $247

                                                            Distance approx 11.33 km from Ghent

                                                              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

                                                              $505

                                                              Price per night from

                                                              $505

                                                              Distance approx 15.05 km from Ghent

                                                                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

                                                                $660

                                                                Price per night from

                                                                $660

                                                                Distance approx 10.48 km from Ghent

                                                                  18

                                                                  Beautiful House in Downtown Hudson, NY

                                                                  New York / Hudson

                                                                  Hudson house

                                                                  6 10 min stay varies

                                                                  • 6 bedrooms
                                                                  • sleeps 10
                                                                  • min stay varies
                                                                  • Nearest beach 201 mi
                                                                  • Child Friendly
                                                                  • Car not necessary

                                                                  Price per night from

                                                                  $574

                                                                  Price per night from

                                                                  $574

                                                                  Distance approx 14.06 km from Ghent

                                                                    18

                                                                    1 Bedroom Hudson Valley Farm House

                                                                    New York / Craryville

                                                                    Craryville guest house

                                                                    1 2 2 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 2
                                                                    • 2 nights min
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $365

                                                                    Price per night from

                                                                    $365

                                                                    Distance approx 19.05 km from Ghent

                                                                      12

                                                                      Beautiful Berkshire Mtn. Condo with Mountain Views, near Tanglewood, Lakes et al

                                                                      Berkshires / Lee

                                                                      Lee condo

                                                                      3 8 30 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 8
                                                                      • 30 nights min
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $249

                                                                      Price per night from

                                                                      $249

                                                                      Distance approx 14.06 km from Ghent

                                                                        18

                                                                        2 Bedroom Hudson Valley Farm House

                                                                        New York / Craryville

                                                                        Craryville guest house

                                                                        2 4 2 nights min

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

                                                                        Price per night from

                                                                        $367

                                                                        Price per night from

                                                                        $367

                                                                        Distance approx 14.06 km from Ghent

                                                                          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

                                                                          $365

                                                                          Price per night from

                                                                          $365

                                                                          Distance approx 13.47 km from Ghent

                                                                          (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

                                                                            $325

                                                                            Price per night from

                                                                            $325

                                                                            Distance approx 13 km from Ghent

                                                                              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