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50 Houses

    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

    $234

    Price per night from

    $234

    Great rentals within 20 miles that match your search

    Distance approx 15.63 km from Sherman

    (5) Excellent 

      24

      Its the Perfect Weekend House just 80min from NYC!

      Connecticut / Woodbury

      Woodbury house

      4 8 2 nights min

      • 4 bedrooms
      • sleeps 8
      • 2 nights min
      • Beach / lakeside relaxation
      • Air conditioning
      • Private garden

      Price per night from

      $177

      Responds fast!
      avg. 2 hours 30 minutes

      Price per night from

      $177

      Distance approx 6.58 km from Sherman Show on Map

        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

        $294

        Responds fast!
        avg. 9 minutes

        Price per night from

        $294

        Distance approx 10.08 km from Sherman

          30

          PoshPadsCT "South Street" 4-BR Cottage with Heated Pool

          Connecticut / Washington

          Washington house

          4 8 min stay varies

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

          Price per night from

          $818

          Price per night from

          $818

          Distance approx 7.08 km from Sherman

            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

            $736

            Price per night from

            $736

            Distance approx 14.65 km from Sherman

            (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

              $187

              Price per night from

              $187

              Distance approx 16.23 km from Sherman

                24

                Prana Residence - Spa

                Connecticut / Cornwall Bridge

                Cornwall Bridge house

                3 7 2 nights min

                • 3 bedrooms
                • sleeps 7
                • 2 nights min
                • Swimming pool
                • Ask about children
                • Air conditioning

                Price per night from

                $883

                Price per night from

                $883

                Distance approx 15.85 km from Sherman

                  8

                  Large Private Apartment

                  New York / Verbank

                  Verbank apartment

                  1 3 1 night min

                  • 1 bedroom
                  • sleeps 3
                  • 1 night min
                  • Child Friendly

                  Price per night from

                  $118

                  Price per night from

                  $118

                  Distance approx 8.98 km from Sherman

                  (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

                    $257

                    Price per night from

                    $257

                    Distance approx 14.15 km from Sherman

                    (1) Excellent 

                      16

                      Wits End Farm

                      Connecticut / Bethlehem

                      Bethlehem house

                      6 12 3 nights min

                      • 6 bedrooms
                      • sleeps 12
                      • 3 nights min
                      • Nearest beach 3 mi
                      • Swimming pool
                      • Child Friendly

                      Price per night from

                      $1,059

                      Price per night from

                      $1,059

                      Distance approx 14.15 km from Sherman

                      (1) Excellent 

                        14

                        Wits End Farm B&B

                        Connecticut / Bethlehem

                        Bethlehem b and b

                        5 10 4 nights min

                        • 5 bedrooms
                        • sleeps 10
                        • 4 nights min
                        • Child Friendly

                        Price per night from

                        $942

                        Price per night from

                        $942

                        Distance approx 15.68 km from Sherman

                          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

                          $165

                          Responds fast!
                          avg. 29 minutes

                          Price per night from

                          $165

                          Distance approx 10.41 km from Sherman

                            8

                            Kent Victorian Room 4

                            Connecticut / Kent

                            Kent room

                            1 2 2 nights min

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

                            Price per night from

                            $130

                            Price per night from

                            $130

                            Distance approx 10.41 km from Sherman

                              8

                              Kent Victorian Room 3

                              Connecticut / Kent

                              Kent room

                              1 2 2 nights min

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

                              Price per night from

                              $176

                              Price per night from

                              $176

                              Distance approx 19.8 km from Sherman

                                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

                                $589

                                Price per night from

                                $589

                                Distance approx 10.41 km from Sherman

                                  8

                                  Kent Victorian Room 2

                                  Connecticut / Kent

                                  Kent room

                                  1 2 2 nights min

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

                                  Price per night from

                                  $176

                                  Price per night from

                                  $176

                                  Distance approx 10.41 km from Sherman

                                    8

                                    Kent Victorian Room 5

                                    Connecticut / Kent

                                    Kent room

                                    2 3 2 nights min

                                    • 2 bedrooms
                                    • sleeps 3
                                    • 2 nights min
                                    • Air conditioning
                                    • Private garden

                                    Price per night from

                                    $187

                                    Price per night from

                                    $187

                                    Distance approx 11.31 km from Sherman

                                      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

                                      $1,177

                                      Responds fast!
                                      avg. 13 minutes

                                      Price per night from

                                      $1,177

                                      Distance approx 10.27 km from Sherman

                                        28

                                        100% ROXBURY! (Zoom in Map++) PoshPadsCT "MOOSEHORN" Mint 5BR Pool, BBQ, Bikes

                                        Washington / Washington Depot

                                        Washington Depot house

                                        5 12 min stay varies

                                        • 5 bedrooms
                                        • sleeps 12
                                        • min stay varies
                                        • Nearest beach 7 mi
                                        • Swimming pool
                                        • Child Friendly

                                        Price per night from

                                        $310

                                        Responds fast!
                                        avg. 54 minutes

                                        Price per night from

                                        $310

                                        Distance approx 10.27 km from Sherman

                                          36

                                          100% ROXBURY! (Zoom Map In++) PoshPadsCT "PAINTER HILL" Mint 4-BR,Pool,Fire,BBQ

                                          Washington / Washington Depot

                                          Washington Depot house

                                          4 14 min stay varies

                                          • 4 bedrooms
                                          • sleeps 14
                                          • min stay varies
                                          • Child Friendly
                                          • Pet Friendly

                                          Price per night from

                                          $271

                                          Responds fast!
                                          avg. 54 minutes

                                          Price per night from

                                          $271

                                          Distance approx 10.27 km from Sherman

                                            34

                                            100% WASHINGTON! (Zoom in Map++) PoshPadsCT "51 SENFF RD" Mint 5BR, Pool, BBQ

                                            Washington / Washington Depot

                                            Washington Depot house

                                            5 10 min stay varies

                                            • 5 bedrooms
                                            • sleeps 10
                                            • min stay varies
                                            • Child Friendly
                                            • Pet Friendly

                                            Price per night from

                                            $310

                                            Responds fast!
                                            avg. 54 minutes

                                            Price per night from

                                            $310

                                            Distance approx 7.16 km from Sherman

                                            (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

                                              $185

                                              Price per night from

                                              $185

                                              Distance approx 10.27 km from Sherman

                                                38

                                                100% ROXBURY! PoshPadsCT "NORTH ST" Private, Mint 6-BR, Pool,Views, Fire Pl, BBQ

                                                Washington / Washington Depot

                                                Washington Depot house

                                                6 12 min stay varies

                                                • 6 bedrooms
                                                • sleeps 12
                                                • min stay varies
                                                • Child Friendly
                                                • Pet Friendly

                                                Price per night from

                                                $271

                                                Responds fast!
                                                avg. 54 minutes

                                                Price per night from

                                                $271

                                                Distance approx 8.85 km from Sherman Show on Map

                                                  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

                                                  $1,030

                                                  Responds fast!
                                                  avg. 54 minutes

                                                  Price per night from

                                                  $1,030

                                                  Distance approx 15.52 km from Sherman

                                                  (1) Excellent 

                                                    11

                                                    Evie's Turning Point Farm

                                                    Connecticut / Warren

                                                    Warren farmhouse

                                                    3 6 2 nights min

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

                                                    Price per night from

                                                    $130

                                                    Price per night from

                                                    $130

                                                    Distance approx 10.74 km from Sherman

                                                      18

                                                      Washington "Plumb Hill" 5-Bedroom, Heated Pool, PoshPadsCT

                                                      Connecticut / Washington

                                                      Washington house

                                                      5 10 min stay varies

                                                      • 5 bedrooms
                                                      • sleeps 10
                                                      • min stay varies
                                                      • Nearest beach 5 mi
                                                      • Swimming pool
                                                      • Child Friendly

                                                      Price per night from

                                                      $271

                                                      Responds fast!
                                                      avg. 54 minutes

                                                      Price per night from

                                                      $271

                                                      Distance approx 13.34 km from Sherman

                                                        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

                                                        $794

                                                        Responds fast!
                                                        avg. 54 minutes

                                                        Price per night from

                                                        $794

                                                        Distance approx 10.13 km from Sherman

                                                          12

                                                          Washington - "Kirby Road" 3-Bedroom Carriage House on the Green - PoshPadsCT

                                                          Connecticut / Washington

                                                          Washington house

                                                          3 6 min stay varies

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

                                                          Price per night from

                                                          $192

                                                          Responds fast!
                                                          avg. 54 minutes

                                                          Price per night from

                                                          $192

                                                          Distance approx 17.76 km from Sherman

                                                            20

                                                            Litchfield Hills Hideaway

                                                            Connecticut / Litchfield

                                                            Litchfield apartment

                                                            1 2 2 nights min

                                                            • 1 bedroom
                                                            • sleeps 2
                                                            • 2 nights min

                                                            Price per night from

                                                            $142

                                                            Responds fast!
                                                            avg. 3 hours 9 minutes

                                                            Price per night from

                                                            $142

                                                            Distance approx 10.27 km from Sherman

                                                              22

                                                              100% WASHINGTON! (Zoom in Map ++) PoshPadsCT "SHEARER RD" Mint 3BR, Pool, BBQ

                                                              Washington / Washington Depot

                                                              Washington Depot house

                                                              3 6 min stay varies

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

                                                              Price per night from

                                                              $232

                                                              Responds fast!
                                                              avg. 54 minutes

                                                              Price per night from

                                                              $232

                                                              Distance approx 13.59 km from Sherman

                                                                36

                                                                100% ROXBURY (Zoom in Map+) PoshPadsCT "PAINTER RIDGE" Mint 3BR, Pool, BBQ,Bikes

                                                                Connecticut / Washington

                                                                Washington house

                                                                3 8 min stay varies

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

                                                                Price per night from

                                                                $271

                                                                Responds fast!
                                                                avg. 54 minutes

                                                                Price per night from

                                                                $271

                                                                Distance approx 10.27 km from Sherman

                                                                  42

                                                                  100% WASHINGTON! (Zoom in Map++) PoshPadsCT "SUNNY RIDGE" 8-BR Estate, Pool, BBQ

                                                                  Washington / Washington Depot

                                                                  Washington Depot house

                                                                  8 16 min stay varies

                                                                  • 8 bedrooms
                                                                  • sleeps 16
                                                                  • min stay varies
                                                                  • Child Friendly

                                                                  Price per night from

                                                                  $389

                                                                  Responds fast!
                                                                  avg. 54 minutes

                                                                  Price per night from

                                                                  $389

                                                                  Distance approx 18.7 km from Sherman

                                                                    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

                                                                    $157

                                                                    Price per night from

                                                                    $157

                                                                    Distance approx 10.27 km from Sherman

                                                                      18

                                                                      100%WashingtonZOOM MAP+PoshPadsCT "Magical Barn"

                                                                      Washington / Washington Depot

                                                                      Washington Depot house

                                                                      5 10 min stay varies

                                                                      • 5 bedrooms
                                                                      • sleeps 10
                                                                      • min stay varies
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $350

                                                                      Responds fast!
                                                                      avg. 54 minutes

                                                                      Price per night from

                                                                      $350

                                                                      Distance approx 14.62 km from Sherman

                                                                        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

                                                                        $106

                                                                        Price per night from

                                                                        $106

                                                                        Distance approx 4.85 km from Sherman Show on Map

                                                                        (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

                                                                          $294

                                                                          Price per night from

                                                                          $294

                                                                          Distance approx 10.84 km from Sherman

                                                                            7

                                                                            2 Bedroom Suite with Kitchen

                                                                            Connecticut / Roxbury

                                                                            Roxbury hotel apartment

                                                                            2 4 1 night min

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

                                                                            Price per night from

                                                                            $293

                                                                            Price per night from

                                                                            $293

                                                                            Distance approx 16.02 km from Sherman

                                                                              20

                                                                              LAKEFRONT COTTAGE ON PRISTINE LAKE

                                                                              New York / Carmel

                                                                              Carmel cottage

                                                                              2 4 7 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • 7 nights min
                                                                              • Beach / lakeside relaxation
                                                                              • Ask about children
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $232

                                                                              Price per night from

                                                                              $232