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76 Houses

    44

    1790 Classic Colonial Center Hall home

    Connecticut / Sharon

    Sharon house

    5 11 2 nights min

    • 5 bedrooms
    • sleeps 11
    • 2 nights min
    • Child Friendly

    Price per night from

    $573

    Price per night from

    $573

    Great rentals within 20 miles that match your search

    Distance approx 10.67 km from Sharon

    (1) Excellent 

      37

      Charming 2+2 Lakeside Cottage on Best Lake in CT

      Connecticut / Salisbury

      Salisbury cottage

      2 4 30 nights min

      • 2 bedrooms
      • sleeps 4
      • 30 nights min
      • Beach / lakeside relaxation
      • Child Friendly

      Price per night from

      $207

      Price per night from

      $207

      Distance approx 4.65 km from Sharon Show on Map

      (1) Excellent 

        13

        Lake House

        Connecticut / Lakeville

        Lakeville house

        5 9 2 nights min

        • 5 bedrooms
        • sleeps 9
        • 2 nights min
        • Child Friendly
        • Pet Friendly

        Price per night from

        $687

        Price per night from

        $687

        Distance approx 18.78 km from Sharon

          27

          Cozy Waterfront Cottage on Copake Lake w/ Dock

          New York / Craryville

          Craryville cottage

          1 4 min stay varies

          • 1 bedroom
          • sleeps 4
          • min stay varies
          • Ski
          • Child Friendly
          • Air conditioning

          Price per night from

          $126

          Responds fast!
          avg. 47 minutes

          Price per night from

          $126

          Distance approx 14.97 km from Sharon

            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 18.19 km from Sharon

              13

              Designer Loft Style Residence

              Berkshires / Sheffield

              Sheffield house

              3 6 7 nights min

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

              Price per night from

              $516

              Responds fast!
              avg. 3 hours 46 minutes

              Price per night from

              $516

              Distance approx 16.91 km from Sharon

                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

                $2,290

                Price per night from

                $2,290

                Distance approx 5.61 km from Sharon Show on Map

                (3) Excellent 

                  42

                  4 Bedroom Furnished House in Lakeville Connecticut

                  Connecticut / Lakeville

                  Lakeville house

                  4 8 2 nights min

                  • 4 bedrooms
                  • sleeps 8
                  • 2 nights min
                  • Child Friendly
                  • Air conditioning
                  • Ask about pets

                  Price per night from

                  $373

                  Price per night from

                  $373

                  Distance approx 19.75 km from Sharon

                    7

                    Secluded House in the Woods w/ Year Round Hot Tub

                    New York / Red Hook

                    Red Hook house

                    2 4 3 nights min

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

                    Price per night from

                    $229

                    Price per night from

                    $229

                    Distance approx 17.08 km from Sharon

                    (2) Excellent 

                      14

                      Newly Renovated Lakefront Getaway on Robinson Pond

                      New York / Copake

                      Copake house

                      3 5 3 nights min

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

                      Price per night from

                      $229

                      Responds fast!
                      avg. 2 hours 34 minutes

                      Price per night from

                      $229

                      Distance approx 16.8 km from Sharon

                        13

                        Modern cabin in the woods + year round heated pool

                        New York / Red Hook

                        Red Hook house

                        3 7 3 nights min

                        • 3 bedrooms
                        • sleeps 7
                        • 3 nights min
                        • Swimming pool
                        • Child Friendly
                        • Pet Friendly

                        Price per night from

                        $275

                        Price per night from

                        $275

                        Distance approx 19.49 km from Sharon

                          10

                          Country Victorian Serenity in the Berkshires

                          Berkshires / New Marlborough

                          New Marlborough house

                          4 6 7 nights min

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

                          Price per night from

                          $263

                          Price per night from

                          $263

                          Distance approx 14.86 km from Sharon

                            24

                            Lakefront New Preston Cottage w/Dock & Fire Pit!

                            Connecticut / New Preston

                            New Preston cottage

                            3 6 min stay varies

                            • 3 bedrooms
                            • sleeps 6
                            • min stay varies
                            • Child Friendly
                            • Pet Friendly

                            Price per night from

                            $229

                            Responds fast!
                            avg. 47 minutes

                            Price per night from

                            $229

                            Distance approx 11.61 km from Sharon

                            (1) Excellent 

                              20

                              Renovated Barn

                              Connecticut / Taconic

                              Taconic house

                              3 6 2 nights min

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

                              Price per night from

                              $401

                              Responds fast!
                              avg. 32 minutes

                              Price per night from

                              $401

                              Distance approx 19.32 km from Sharon

                                20

                                Beautiful Lake House - Magnificent in all 4 Seasons 3 Bed, 2 Bath

                                Connecticut / Winsted

                                Winsted house

                                3 6 min stay varies

                                • 3 bedrooms
                                • sleeps 6
                                • min stay varies
                                • Child Friendly
                                • Air conditioning
                                • Private garden

                                Price per night from

                                $258

                                Responds fast!
                                avg. 2 hours 31 minutes

                                Price per night from

                                $258

                                Distance approx 19.29 km from Sharon

                                (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 19.1 km from Sharon

                                    36

                                    Spacious Berkshires Home w/ Pool & Patio!

                                    Berkshires / North Egremont

                                    North Egremont house

                                    5 10 2 nights min

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

                                    Price per night from

                                    $859

                                    Responds fast!
                                    avg. 47 minutes

                                    Price per night from

                                    $859

                                    Distance approx 17.41 km from Sharon

                                    (1) Excellent 

                                      25

                                      Litchfield House on Half Acre - 1 Mile to Town!

                                      Connecticut / Litchfield

                                      Litchfield house

                                      3 7 min stay varies

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

                                      Price per night from

                                      $243

                                      Responds fast!
                                      avg. 47 minutes

                                      Price per night from

                                      $243

                                      Distance approx 19.31 km from Sharon

                                        22

                                        Woodland House - sleeps 10 in luxury

                                        New York / Rhinebeck

                                        Rhinebeck house

                                        5 10 2 nights min

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

                                        Price per night from

                                        $686

                                        Price per night from

                                        $686

                                        Distance approx 16.15 km from Sharon

                                        (1) Excellent 

                                          14

                                          The perfect Southern Berkshire winter vacation esc

                                          Berkshires / Sheffield

                                          Sheffield house

                                          4 10 7 nights min

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

                                          Price per night from

                                          $573

                                          Price per night from

                                          $573

                                          Distance approx 18.95 km from Sharon

                                            25

                                            Dutchess County Guest House on Working Horse Farm!

                                            New York / Salt Point

                                            Salt Point house

                                            3 6 min stay varies

                                            • 3 bedrooms
                                            • sleeps 6
                                            • min stay varies
                                            • Child Friendly
                                            • Air conditioning
                                            • Pet Friendly

                                            Price per night from

                                            $321

                                            Responds fast!
                                            avg. 47 minutes

                                            Price per night from

                                            $321

                                            Distance approx 19.44 km from Sharon

                                              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 14.47 km from Sharon

                                                25

                                                Lakefront Warren 'Carriage House' on 25 Acres!

                                                Connecticut / Warren

                                                Warren house

                                                7 14 4 nights min

                                                • 7 bedrooms
                                                • sleeps 14
                                                • 4 nights min
                                                • Ski
                                                • Child Friendly
                                                • Air conditioning

                                                Price per night from

                                                $1,145

                                                Responds fast!
                                                avg. 37 minutes

                                                Price per night from

                                                $1,145

                                                Distance approx 19.81 km from Sharon

                                                  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

                                                  $686

                                                  Price per night from

                                                  $686

                                                  Distance approx 15.41 km from Sharon

                                                    24

                                                    NEW-Norfolk Countryside Home 30 Min to Ski Sundown

                                                    Connecticut / Norfolk

                                                    Norfolk house

                                                    4 5 min stay varies

                                                    • 4 bedrooms
                                                    • sleeps 5
                                                    • min stay varies
                                                    • Ski
                                                    • Child Friendly

                                                    Price per night from

                                                    $247

                                                    Responds fast!
                                                    avg. 47 minutes

                                                    Price per night from

                                                    $247

                                                    Distance approx 17.8 km from Sharon

                                                      14

                                                      Washington "Shearer" 3-Bedroom Country Cottage - PoshPadsCT

                                                      Connecticut / Washington

                                                      Washington house

                                                      3 7 min stay varies

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

                                                      Price per night from

                                                      $773

                                                      Price per night from

                                                      $773

                                                      Distance approx 4.84 km from Sharon Show on Map

                                                        4

                                                        Exclusive Rental in Beautiful Amenia!

                                                        New York / Amenia

                                                        Amenia house

                                                        3 6 30 nights min

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

                                                        Price per night from

                                                        $153

                                                        Price per night from

                                                        $153

                                                        Distance approx 7.21 km from Sharon Show on Map

                                                          12

                                                          Cottage on East Twin Lakes, Internet Access, A/C.

                                                          Connecticut / Salisbury

                                                          Salisbury cottage

                                                          3 6 7 nights min

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

                                                          Price per night from

                                                          $180

                                                          Price per night from

                                                          $180

                                                          Distance approx 10.72 km from Sharon

                                                            6

                                                            Kent Victorian Room 1

                                                            Connecticut / Kent

                                                            Kent room

                                                            1 2 2 nights min

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

                                                            Price per night from

                                                            $182

                                                            Price per night from

                                                            $182

                                                            Distance approx 19.58 km from Sharon

                                                              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

                                                              $367

                                                              Price per night from

                                                              $367

                                                              Distance approx 17.88 km from Sharon

                                                                21

                                                                Washington - "Senff 8-BR Estate" Heated Pool, Private Scenic Estate Neighborhood

                                                                Connecticut / Washington

                                                                Washington house

                                                                8 14 min stay varies

                                                                • 8 bedrooms
                                                                • sleeps 14
                                                                • min stay varies
                                                                • Nearest beach 5 mi
                                                                • Swimming pool
                                                                • Child Friendly

                                                                Price per night from

                                                                $340

                                                                Price per night from

                                                                $340

                                                                Distance approx 19.87 km from Sharon

                                                                  17

                                                                  Picturesque 19th century home on 3 private acres

                                                                  Berkshires / New Marlborough

                                                                  New Marlborough house

                                                                  4 7 min stay varies

                                                                  • 4 bedrooms
                                                                  • sleeps 7
                                                                  • min stay varies
                                                                  • Child Friendly
                                                                  • Private garden

                                                                  Price per night from

                                                                  $172

                                                                  Price per night from

                                                                  $172

                                                                  Distance approx 17.06 km from Sharon

                                                                    32

                                                                    Summer or Summer Monthly Swimming Lake Rhinebeck Oasis

                                                                    New York / Rhinebeck

                                                                    Rhinebeck house

                                                                    3 8 30 nights min

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

                                                                    Price per night from

                                                                    $267

                                                                    Price per night from

                                                                    $267

                                                                    Distance approx 16.89 km from Sharon

                                                                      24

                                                                      100%WASHINGTON! Zoom In Map PoshPadsCT"Calhoun" 4BR, Views!,Meadows,Pool,25Acres

                                                                      Washington / Washington Depot

                                                                      Washington Depot house

                                                                      4 8 min stay varies

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

                                                                      Price per night from

                                                                      $264

                                                                      Price per night from

                                                                      $264

                                                                      Distance approx 19.58 km from Sharon

                                                                        18

                                                                        4 Bedroom Hudson Valley Farm House

                                                                        New York / Craryville

                                                                        Craryville guest house

                                                                        4 8 2 nights min

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

                                                                        Price per night from

                                                                        $367

                                                                        Price per night from

                                                                        $367

                                                                        Distance approx 19.58 km from Sharon

                                                                          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

                                                                          $367

                                                                          Price per night from

                                                                          $367

                                                                          Distance approx 19.58 km from Sharon

                                                                            18

                                                                            Hudson Valley Farm House

                                                                            New York / Craryville

                                                                            Craryville house

                                                                            5 12 2 nights min

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

                                                                            Price per night from

                                                                            $367

                                                                            Price per night from

                                                                            $367

                                                                            Distance approx 5.62 km from Sharon Show on Map

                                                                            (3) Very Good 

                                                                              22

                                                                              Comfortable Rustic Cottage on 4 Wooded Acres with Brook

                                                                              Connecticut / West Cornwall

                                                                              West Cornwall cottage

                                                                              2 6 2 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 6
                                                                              • 2 nights min
                                                                              • Nearest beach 12 mi
                                                                              • Child Friendly
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $172

                                                                              Price per night from

                                                                              $172