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38 Houses

Great rentals within 20 miles that match your search

Distance approx 11.06 km from Brewster

    15

    LUXURY COTTAGE

    Westchester County / Pound Ridge

    Pound Ridge cottage

    1 4 2 nights min

    • 1 bedroom
    • sleeps 4
    • 2 nights min
    • Ask about children
    • Ask about pets

    Price per night from

    $315

    Responds fast!
    avg. 2 hours 6 minutes

    Price per night from

    $315

    Distance approx 17.49 km from Brewster

    (4) Excellent 

      24

      Beautiful 4 br in historic Cold Spring!

      New York / Cold Spring

      Cold Spring house

      4 8 2 nights min

      • 4 bedrooms
      • sleeps 8
      • 2 nights min
      • Child Friendly
      • Car not necessary
      • Air conditioning

      Price per night from

      $458

      Price per night from

      $458

      Distance approx 14.47 km from Brewster

        10

        Country Chic Cabin~spacious~ private setting~hot tub~pool~ views~75 minutes/NYC

        New York / Garrison

        Garrison house

        3 12 2 nights min

        • 3 bedrooms
        • sleeps 12
        • 2 nights min
        • Child Friendly

        Price per night from

        $1,260

        Price per night from

        $1,260

        Distance approx 19.67 km from Brewster

        (1) Excellent 

          27

          Quiet Getaway in Historic Village

          Connecticut / Southbury

          Southbury house

          2 6 1 night min

          • 2 bedrooms
          • sleeps 6
          • 1 night min
          • Nearest beach 3 mi
          • Child Friendly
          • Car not necessary

          Price per night from

          $182

          Price per night from

          $182

          Distance approx 19.76 km from Brewster

            14

            1 Bedroom Getaway West Point & Bear Mountain area

            New York / Fort Montgomery

            Fort Montgomery apartment

            1 4 1 night min

            • 1 bedroom
            • sleeps 4
            • 1 night min
            • Child Friendly
            • Private garden

            Price per night from

            $212

            Price per night from

            $212

            Distance approx 10.55 km from Brewster

              24

              Unique New Fairfield House w/ Deck & Lake Views!

              Connecticut / New Fairfield

              New Fairfield house

              3 10 min stay varies

              • 3 bedrooms
              • sleeps 10
              • min stay varies
              • Child Friendly
              • Air conditioning

              Price per night from

              $287

              Responds fast!
              avg. 33 minutes

              Price per night from

              $287

              Distance approx 8.94 km from Brewster Show on Map

                32

                Lake House with Indoor Spa, 1 hour from Manhattan

                New York / Carmel

                Carmel house

                3 6 2 nights min

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

                Price per night from

                $229

                Price per night from

                $229

                Distance approx 19.75 km from Brewster

                  29

                  Lake House Rental On Your Own Private Lake

                  New York / Wingdale

                  Wingdale villa

                  4 11 4 nights min

                  • 4 bedrooms
                  • sleeps 11
                  • 4 nights min
                  • Beach / lakeside relaxation
                  • Child Friendly
                  • Air conditioning

                  Price per night from

                  $716

                  Price per night from

                  $716

                  Distance approx 18.01 km from Brewster

                    12

                    Stone Croft Cottage

                    Westchester County / Chappaqua

                    Chappaqua cottage

                    1 4 4 nights min

                    • 1 bedroom
                    • sleeps 4
                    • 4 nights min
                    • Child Friendly
                    • Car not necessary
                    • Air conditioning

                    Price per night from

                    $149

                    Price per night from

                    $149

                    Distance approx 12.19 km from Brewster

                      10

                      Spectacular Lake House

                      New York / Putnam Valley

                      Putnam Valley house

                      3 6 30 nights min

                      • 3 bedrooms
                      • sleeps 6
                      • 30 nights min
                      • Child Friendly
                      • Air conditioning
                      • Private garden

                      Price per night from

                      $418

                      Price per night from

                      $418

                      Distance approx 15.29 km from Brewster

                      (5) Excellent 

                      Certificate of Excellence

                        15

                        Castle By The Lake

                        New York / Putnam Valley

                        Putnam Valley house

                        4 12 min stay varies

                        • 4 bedrooms
                        • sleeps 12
                        • min stay varies
                        • Air conditioning
                        • Private garden

                        Certificate of Excellence

                        Price per night from

                        $241

                        Responds fast!
                        avg. 1 hour 9 minutes

                        Price per night from

                        $241

                        Distance approx 15.27 km from Brewster

                          14

                          PineTop

                          New York / Cold Spring

                          Cold Spring house

                          5 9 2 nights min

                          • 5 bedrooms
                          • sleeps 9
                          • 2 nights min
                          • Swimming pool
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $859

                          Price per night from

                          $859

                          Distance approx 17.58 km from Brewster

                          (4) Excellent 

                            36

                            20'x40' inground private pool just for you&house with 4bedrooms

                            Connecticut / New Milford

                            New Milford house

                            4 8 7 nights min

                            • 4 bedrooms
                            • sleeps 8
                            • 7 nights min
                            • Beach / lakeside relaxation
                            • Nearest beach 13 mi
                            • Swimming pool
                            “Wonderful experience!!!” My wife and our two children (10 and 7)spent a wonderful time at this beautiful New Milford retreat. The house was spacious and nicely decorated and we loved the privacy of the place. You couldn't see any neighbors and yet sho
                            …see more

                            Price per night from

                            $328

                            Responds fast!
                            avg. 1 hour 40 minutes

                            Price per night from

                            $328

                            Distance approx 16.33 km from Brewster

                              15

                              An Oasis in the Hudson Valley

                              Westchester County / Croton on Hudson

                              Croton on Hudson apartment

                              1 2 2 nights min

                              • 1 bedroom
                              • sleeps 2
                              • 2 nights min
                              • Nearest beach 32 mi
                              • Swimming pool
                              • Suitable for children age 5+

                              Price per night from

                              $189

                              Price per night from

                              $189

                              Distance approx 11.68 km from Brewster

                              (9) Very Good 

                                20

                                Lake Bliss the Perfect Getaway

                                New York / Holmes

                                Holmes house

                                3 10 1 night min

                                • 3 bedrooms
                                • sleeps 10
                                • 1 night min
                                • Beach / lakeside relaxation
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $250

                                Price per night from

                                $250

                                Distance approx 13.45 km from Brewster

                                  14

                                  Lake Cottage with Views and Fireplace

                                  Connecticut / Sherman

                                  Sherman house

                                  2 5 2 nights min

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

                                  Price per night from

                                  $228

                                  Responds fast!
                                  avg. 1 hour 16 minutes

                                  Price per night from

                                  $228

                                  Distance approx 17.28 km from Brewster

                                  (2) Excellent 

                                    11

                                    Westchester Hudson Valley Estate - Private, less than 1 hour from NYC

                                    Westchester County / Croton on Hudson

                                    Croton on Hudson villa

                                    8 24 2 nights min

                                    • 8 bedrooms
                                    • sleeps 24
                                    • 2 nights min
                                    • Child Friendly
                                    • Car not necessary
                                    • Air conditioning

                                    Price per night from

                                    $2,519

                                    Price per night from

                                    $2,519

                                    Distance approx 16.6 km from Brewster

                                      42

                                      Spectacular Modern Home Near NYC

                                      Connecticut / Weston

                                      Weston house

                                      5 8 2 nights min

                                      • 5 bedrooms
                                      • sleeps 8
                                      • 2 nights min
                                      • Child Friendly
                                      • Air conditioning

                                      Price per night from

                                      $1,025

                                      Responds fast!
                                      avg. 1 hour 49 minutes

                                      Price per night from

                                      $1,025

                                      Distance approx 16.99 km from Brewster

                                        38

                                        Country Retreat Hot Tub+ Pool+Sauna + more relaxation guaranteed

                                        New York / Garrison

                                        Garrison house

                                        5 15 2 nights min

                                        • 5 bedrooms
                                        • sleeps 15
                                        • 2 nights min
                                        • Child Friendly

                                        Price per night from

                                        $1,718

                                        Price per night from

                                        $1,718

                                        Distance approx 19.65 km from Brewster

                                          12

                                          A Historic Home for Guests and Lawns/Facilities for Gatherings such as Weddings

                                          Connecticut / Southbury

                                          Southbury house

                                          3 8 1 night min

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

                                          Price per night from

                                          $228

                                          Price per night from

                                          $228

                                          Distance approx 15.66 km from Brewster

                                            28

                                            independent room with office and kitchen

                                            Cortlandt / Cortlandt Manor

                                            Cortlandt Manor b and b

                                            1 2 1 night min

                                            • 1 bedroom
                                            • sleeps 2
                                            • 1 night min
                                            • Nearest beach 8 mi
                                            • Child Friendly
                                            • Air conditioning

                                            Price per night from

                                            $58

                                            Responds fast!
                                            avg. 1 hour 48 minutes

                                            Price per night from

                                            $58

                                            Distance approx 13.65 km from Brewster

                                              24

                                              Victorian Newtown Apt w/Fire Pit 20 Mi to Jennings

                                              Connecticut / Newtown

                                              Newtown apartment

                                              1 4 min stay varies

                                              • 1 bedroom
                                              • sleeps 4
                                              • min stay varies
                                              • Ski

                                              Price per night from

                                              $161

                                              Responds fast!
                                              avg. 33 minutes

                                              Price per night from

                                              $161

                                              Distance approx 17.35 km from Brewster

                                              (3) Very Good 

                                                21

                                                Serene Connecticut Retreat - Luxury 2 bedroom apt

                                                Connecticut / Stamford

                                                Stamford apartment

                                                2 4 min stay varies

                                                • 2 bedrooms
                                                • sleeps 4
                                                • min stay varies
                                                • Ask about children
                                                • Car not necessary
                                                • Air conditioning

                                                Price per night from

                                                $212

                                                Responds fast!
                                                avg. 1 hour 29 minutes

                                                Price per night from

                                                $212

                                                Distance approx 18.18 km from Brewster

                                                  5

                                                  Adorable Guest Cottage

                                                  Connecticut / Weston

                                                  Weston cottage

                                                  2 4 1 night min

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

                                                  Price per night from

                                                  $178

                                                  Price per night from

                                                  $178

                                                  Distance approx 18.59 km from Brewster

                                                    1

                                                    Base Camp - Dutch Colonial Estate

                                                    New York / Beacon

                                                    Beacon apartment

                                                    1 2 2 nights min

                                                    • 1 bedroom
                                                    • sleeps 2
                                                    • 2 nights min
                                                    • Air conditioning

                                                    Price per night from

                                                    $258

                                                    Price per night from

                                                    $258

                                                    Distance approx 17.49 km from Brewster

                                                      29

                                                      Very private,4bdrm house,20x40inground pool, pool house. Paradise!

                                                      Connecticut / New Milford

                                                      New Milford house

                                                      4 8 3 nights min

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

                                                      Price per night from

                                                      $401

                                                      Price per night from

                                                      $401

                                                      Distance approx 18.04 km from Brewster

                                                      (4) Excellent 

                                                        12

                                                        Our Rockbound Highland Home * 2 Blocks to West Point * 1/2 Block to Main St

                                                        New York / West Point

                                                        West Point house

                                                        3 11 min stay varies

                                                        • 3 bedrooms
                                                        • sleeps 11
                                                        • min stay varies
                                                        • Child Friendly
                                                        • Air conditioning
                                                        • Private garden

                                                        Price per night from

                                                        $338

                                                        Responds fast!
                                                        avg. 40 minutes

                                                        Price per night from

                                                        $338

                                                        Distance approx 18.35 km from Brewster

                                                          71

                                                          West Point Retreat ✭ 2 BRAND NEW Homes ✭ 6 Bd 4 Ba

                                                          New York / Highland Falls

                                                          Highland Falls house

                                                          6 16 min stay varies

                                                          • 6 bedrooms
                                                          • sleeps 16
                                                          • min stay varies
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $291

                                                          Price per night from

                                                          $291

                                                          Distance approx 19.68 km from Brewster

                                                            17

                                                            Roxbury "Judd's Bridge" 5-BR with Heated Pool, PoshPadsCT

                                                            Connecticut / Roxbury

                                                            Roxbury house

                                                            4 10 min stay varies

                                                            • 4 bedrooms
                                                            • sleeps 10
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Child Friendly
                                                            • Air conditioning

                                                            Price per night from

                                                            $1,002

                                                            Price per night from

                                                            $1,002

                                                            Distance approx 18.07 km from Brewster

                                                              9

                                                              2 bedroom cottage

                                                              New York / Garrison

                                                              Garrison house

                                                              2 4 30 nights min

                                                              • 2 bedrooms
                                                              • sleeps 4
                                                              • 30 nights min
                                                              • Child Friendly
                                                              • Pet Friendly
                                                              • Private garden

                                                              Price per night from

                                                              $69

                                                              Responds fast!
                                                              avg. 1 hour 50 minutes

                                                              Price per night from

                                                              $69

                                                              Distance approx 18.35 km from Brewster

                                                                39

                                                                Beautiful BRAND NEW 3 Bd Home near West Point!

                                                                New York / Highland Falls

                                                                Highland Falls house

                                                                3 12 min stay varies

                                                                • 3 bedrooms
                                                                • sleeps 12
                                                                • min stay varies
                                                                • Child Friendly
                                                                • Air conditioning

                                                                Price per night from

                                                                $146

                                                                Price per night from

                                                                $146

                                                                Distance approx 12.29 km from Brewster

                                                                (1) Excellent 

                                                                  31

                                                                  Private Lakefront & Pool DeeLuxGlamping. NYC Getaway

                                                                  New York / Pawling

                                                                  Pawling camper van

                                                                  2 8 1 night min

                                                                  • 2 bedrooms
                                                                  • sleeps 8
                                                                  • 1 night min
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $180

                                                                  Price per night from

                                                                  $180

                                                                  Distance approx 18.35 km from Brewster

                                                                    38

                                                                    Built in 2018 3BR Luxury House near West Point

                                                                    New York / Highland Falls

                                                                    Highland Falls house

                                                                    3 12 min stay varies

                                                                    • 3 bedrooms
                                                                    • sleeps 12
                                                                    • min stay varies
                                                                    • Child Friendly
                                                                    • Air conditioning

                                                                    Price per night from

                                                                    $146

                                                                    Price per night from

                                                                    $146

                                                                    Distance approx 16.57 km from Brewster

                                                                      30

                                                                      COZY RETREAT: HOT TUB, POOL, SAUNA, AND MORE...

                                                                      New York / Garrison

                                                                      Garrison house

                                                                      5 15 min stay varies

                                                                      • 5 bedrooms
                                                                      • sleeps 15
                                                                      • min stay varies
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $1,432

                                                                      Price per night from

                                                                      $1,432

                                                                      Distance approx 18.6 km from Brewster

                                                                      (1) Excellent 

                                                                        50

                                                                        Croton Lodge: Luxury 2bd⭐Comfort+Style⭐45min to NYC,Great Food.7 nights max stay

                                                                        Westchester County / Croton on Hudson

                                                                        Croton on Hudson apartment

                                                                        2 6 1 night min

                                                                        • 2 bedrooms
                                                                        • sleeps 6
                                                                        • 1 night min
                                                                        • Nearest beach 2 mi
                                                                        • Child Friendly
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $91

                                                                        Price per night from

                                                                        $91

                                                                        Distance approx 19.71 km from Brewster

                                                                          8

                                                                          Library Bed Room with Fireplace, Dressing Room and Separate Entry from outside

                                                                          Connecticut / Southbury

                                                                          Southbury room

                                                                          1 2 2 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 2
                                                                          • 2 nights min
                                                                          • Private garden

                                                                          Price per night from

                                                                          $103

                                                                          Price per night from

                                                                          $103

                                                                          Distance approx 19 km from Brewster

                                                                            19

                                                                            ROMANTIC GETAWAY COTTAGE ON WATER

                                                                            New York / Beacon

                                                                            Beacon cottage

                                                                            3 8 2 nights min

                                                                            • 3 bedrooms
                                                                            • sleeps 8
                                                                            • 2 nights min
                                                                            • Child Friendly
                                                                            • Car not necessary
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $258

                                                                            Responds fast!
                                                                            avg. 2 hours 2 minutes

                                                                            Price per night from

                                                                            $258

                                                                            Distance approx 14.2 km from Brewster

                                                                            (1)  

                                                                              32

                                                                              Must Love Garden and the Sound of Stream

                                                                              New York / Lanesville

                                                                              Lanesville house

                                                                              4 9 1 night min

                                                                              • 4 bedrooms
                                                                              • sleeps 9
                                                                              • 1 night min
                                                                              • Child Friendly
                                                                              • Pet Friendly

                                                                              Price per night from

                                                                              $287

                                                                              Price per night from

                                                                              $287