Madison Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

Filtering by: Garden

51 Houses

    12

    Spacious studio near beach

    Connecticut / Madison

    Madison studio

    Studio 3 1 night min

    • Studio
    • sleeps 3
    • 1 night min
    • Swimming pool
    • Child Friendly
    • Air conditioning

    Price per night from

    $80

    Price per night from

    $80

    (13) Excellent 

      17

      Adorable summer cottage on Connecticut Shoreline

      Connecticut / Madison

      Madison cottage

      1 4 min stay varies

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

      Price per night from

      $97

      Responds fast!
      avg. 3 hours 23 minutes

      Price per night from

      $97

      Great rentals within 20 miles that match your search

      Distance approx 19.74 km from Madison

        15

        Southold Summer Home for rent

        North Fork / Southold

        Southold house

        3 6 7 nights min

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

        Price per night from

        $526

        Price per night from

        $526

        Distance approx 9.65 km from Madison

        (16) Excellent 

          17

          Ennis Cottage with private beach on Branford shore

          Connecticut / Branford

          Branford cottage

          1 2 min stay varies

          • 1 bedroom
          • sleeps 2
          • min stay varies
          • Beach / lakeside relaxation
          • Nearest beach 0 mi
          • Child Friendly
          “Wonderful stay in a great cottage” Our stay at Ennis Cottage was perfect, we could not have wished for nicer accommodation. Ron and Bernie were very welcoming and the cottage had everything we needed for our stay. We have a ten month old baby and they

          Price per night from

          $160

          Responds fast!
          avg. 2 hours 15 minutes

          Price per night from

          $160

          Distance approx 18.05 km from Madison

          (3) Very Good 

            22

            $500 off Book by 4/31/19 CT Lake Front Victorian Mansion Truly Memorable

            Connecticut / East Haddam

            East Haddam house

            7 22 6 nights min

            • 7 bedrooms
            • sleeps 22
            • 6 nights min
            • Beach / lakeside relaxation
            • Nearest beach 32 mi
            • Child Friendly
            “We can't wait to come again!!” Wanted to Thank you for a "Truly Memorable" time. Our entire family want to return to this magical place. We swam, fished, canoed, played volleyball,you name it someone was ready. My wife enjoyed the hammock and balconie

            Price per night from

            $922

            Price per night from

            $922

            Distance approx 18.93 km from Madison

              14

              North Fork Long Island Wine Country Cottage, Water Views

              North Fork / Cutchogue

              Cutchogue house

              2 6 7 nights min

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

              Price per night from

              $314

              Price per night from

              $314

              Distance approx 17.31 km from Madison

                19

                Southold Contemporary Summer Home Steps from Beach and Vineyard

                North Fork / Southold

                Southold house

                3 6 14 nights min

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

                Price per night from

                $428

                Price per night from

                $428

                Distance approx 17.3 km from Madison

                  25

                  Founders Landing Saltwater Inground Heated Pool. Walk to Beach,Town, Restaurants

                  North Fork / Southold

                  Southold house

                  4 8 7 nights min

                  • 4 bedrooms
                  • sleeps 8
                  • 7 nights min
                  • Nearest beach 0.5 mi
                  • Swimming pool
                  • Child Friendly

                  Price per night from

                  $651

                  Price per night from

                  $651

                  Distance approx 16.94 km from Madison

                    16

                    Greenport Village Home Walking Distance to All

                    North Fork / Greenport

                    Greenport farmhouse

                    3 8 30 nights min

                    • 3 bedrooms
                    • sleeps 8
                    • 30 nights min
                    • Beach / lakeside relaxation
                    • Child Friendly
                    • Car not necessary

                    Price per night from

                    $590

                    Price per night from

                    $590

                    Distance approx 16.81 km from Madison

                      13

                      Remodeled Greenport Farmhouse

                      North Fork / Greenport

                      Greenport farmhouse

                      3 6 14 nights min

                      • 3 bedrooms
                      • sleeps 6
                      • 14 nights min
                      • Beach / lakeside relaxation
                      • Child Friendly
                      • Air conditioning

                      Price per night from

                      $485

                      Price per night from

                      $485

                      Distance approx 19.74 km from Madison

                        13

                        North Fork Loft - Perfect for Wine & Food Weekends

                        North Fork / Mattituck

                        Mattituck apartment

                        5 14 2 nights min

                        • 5 bedrooms
                        • sleeps 14
                        • 2 nights min
                        • Beach / lakeside relaxation
                        • Nearest beach 4 mi
                        • Ask about children

                        Price per night from

                        $1,021

                        Price per night from

                        $1,021

                        Distance approx 15.48 km from Madison

                          15

                          Luxurious living on a bucolic alpaca farm

                          Connecticut / Lyme

                          Lyme house

                          2 6 2 nights min

                          • 2 bedrooms
                          • sleeps 6
                          • 2 nights min
                          • Nearest beach 5 mi
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $229

                          Price per night from

                          $229

                          Distance approx 17.49 km from Madison

                            34

                            Beach Cottage, Bring The Dog, Founders Landing Beach, Southold, North Fork, NY

                            North Fork / Southold

                            Southold house

                            2 4 5 nights min

                            • 2 bedrooms
                            • sleeps 4
                            • 5 nights min
                            • Nearest beach 1 mi
                            • Child Friendly
                            • Air conditioning

                            Price per night from

                            $398

                            Price per night from

                            $398

                            Distance approx 17 km from Madison

                            (1) Excellent 

                              35

                              The Victorian Seasons Cape

                              North Fork / East Marion

                              East Marion cottage

                              3 5 3 nights min

                              • 3 bedrooms
                              • sleeps 5
                              • 3 nights min
                              • Child Friendly
                              • Air conditioning
                              • Private garden

                              Price per night from

                              $571

                              Price per night from

                              $571

                              Distance approx 5.54 km from Madison

                              (2) Very Good 

                                38

                                Charming 6 Bedroom Oceanfront Cottage By The Sea

                                Connecticut / Clinton

                                Clinton cottage

                                6 10 min stay varies

                                • 6 bedrooms
                                • sleeps 10
                                • min stay varies
                                • Beach / lakeside relaxation
                                • Child Friendly
                                • Private garden

                                Price per night from

                                $229

                                Responds fast!
                                avg. 47 minutes

                                Price per night from

                                $229

                                Distance approx 17 km from Madison

                                (1) Excellent 

                                  21

                                  Victorian Seasons 1 bedroom Carriage House Duplex

                                  North Fork / East Marion

                                  East Marion apartment

                                  1 2 2 nights min

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

                                  Price per night from

                                  $371

                                  Price per night from

                                  $371

                                  Distance approx 16.81 km from Madison

                                  (1) Excellent 

                                    17

                                    Relaxed Village Farmhouse

                                    North Fork / Greenport

                                    Greenport house

                                    4 8 min stay varies

                                    • 4 bedrooms
                                    • sleeps 8
                                    • min stay varies
                                    • Air conditioning
                                    • Private garden

                                    Price per night from

                                    $457

                                    Responds fast!
                                    avg. 1 hour 16 minutes

                                    Price per night from

                                    $457

                                    Distance approx 18.59 km from Madison

                                      4

                                      Beautiful Luxury Home with Pool in the Heart of Wine Country

                                      North Fork / Cutchogue

                                      Cutchogue house

                                      4 10 2 nights min

                                      • 4 bedrooms
                                      • sleeps 10
                                      • 2 nights min
                                      • Nearest beach 3 mi
                                      • Swimming pool
                                      • Child Friendly

                                      Price per night from

                                      $799

                                      Responds fast!
                                      avg. 3 hours 56 minutes

                                      Price per night from

                                      $799

                                      Distance approx 18.73 km from Madison

                                        10

                                        Royal Master Suite

                                        Connecticut / Hamden

                                        Hamden private room

                                        1 2 1 night min

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

                                        Price per night from

                                        $103

                                        Responds fast!
                                        avg. 2 hours 25 minutes

                                        Price per night from

                                        $103

                                        Distance approx 19.33 km from Madison

                                          24

                                          Beach Front, spacious 5 Bedrooms, North Fork, Long Island

                                          North Fork / Southold

                                          Southold house

                                          5 12 min stay varies

                                          • 5 bedrooms
                                          • sleeps 12
                                          • min stay varies
                                          • Child Friendly
                                          • Air conditioning
                                          • Private garden

                                          Price per night from

                                          $600

                                          Price per night from

                                          $600

                                          Distance approx 4.74 km from Madison

                                          (1) Excellent 

                                            19

                                            Steps to beach 4bd 2 bth Sleeps 14

                                            Connecticut / Clinton

                                            Clinton house

                                            3 14 min stay varies

                                            • 3 bedrooms
                                            • sleeps 14
                                            • min stay varies
                                            • Child Friendly
                                            • Air conditioning
                                            • Pet Friendly

                                            Price per night from

                                            $240

                                            Price per night from

                                            $240

                                            Distance approx 16.28 km from Madison

                                            (6) Excellent 

                                              14

                                              North Fork House with Private Beach Access

                                              North Fork / East Marion

                                              East Marion house

                                              4 8 7 nights min

                                              • 4 bedrooms
                                              • sleeps 8
                                              • 7 nights min
                                              • Child Friendly
                                              • Air conditioning
                                              • Pet Friendly

                                              Price per night from

                                              $342

                                              Responds fast!
                                              avg. 3 hours 14 minutes

                                              Price per night from

                                              $342

                                              Distance approx 17.94 km from Madison

                                                32

                                                Clarke's Landing

                                                Connecticut / Middlefield

                                                Middlefield house

                                                3 8 min stay varies

                                                • 3 bedrooms
                                                • sleeps 8
                                                • min stay varies
                                                • Beach / lakeside relaxation
                                                • Nearest beach 0.1 mi
                                                • Child Friendly

                                                Price per night from

                                                $343

                                                Responds fast!
                                                avg. 3 hours 50 minutes

                                                Price per night from

                                                $343

                                                Distance approx 13.39 km from Madison

                                                  67

                                                  Cosey Beach House

                                                  Connecticut / East Haven

                                                  East Haven house

                                                  4 10 min stay varies

                                                  • 4 bedrooms
                                                  • sleeps 10
                                                  • min stay varies
                                                  • Child Friendly
                                                  • Private garden

                                                  Price per night from

                                                  $571

                                                  Responds fast!
                                                  avg. 3 hours 50 minutes

                                                  Price per night from

                                                  $571

                                                  Distance approx 19.47 km from Madison

                                                    23

                                                    North Fork retreat walking distance to Peconic bay beach

                                                    North Fork / Cutchogue

                                                    Cutchogue house

                                                    3 8 14 nights min

                                                    • 3 bedrooms
                                                    • sleeps 8
                                                    • 14 nights min
                                                    • Nearest beach 3 mi
                                                    • Child Friendly
                                                    • Air conditioning

                                                    Price per night from

                                                    $457

                                                    Price per night from

                                                    $457

                                                    Distance approx 15.37 km from Madison

                                                      20

                                                      Sleep well in our beautiful North Haven, CT home

                                                      Connecticut / North Haven

                                                      North Haven house

                                                      4 8 2 nights min

                                                      • 4 bedrooms
                                                      • sleeps 8
                                                      • 2 nights min
                                                      • Child Friendly
                                                      • Pet Friendly
                                                      • Private garden

                                                      Price per night from

                                                      $170

                                                      Price per night from

                                                      $170

                                                      Distance approx 16.79 km from Madison

                                                        16

                                                        Historic Cottage Near Beach!

                                                        North Fork / Greenport

                                                        Greenport house

                                                        2 4 60 nights min

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • 60 nights min
                                                        • Air conditioning
                                                        • Ask about pets
                                                        • Private garden

                                                        Price per night from

                                                        $381

                                                        Price per night from

                                                        $381

                                                        Distance approx 17.94 km from Madison

                                                          17

                                                          Betty's Boat House

                                                          Connecticut / Middlefield

                                                          Middlefield house

                                                          2 4 min stay varies

                                                          • 2 bedrooms
                                                          • sleeps 4
                                                          • min stay varies
                                                          • Beach / lakeside relaxation
                                                          • Nearest beach 0.1 mi
                                                          • Child Friendly

                                                          Price per night from

                                                          $143

                                                          Responds fast!
                                                          avg. 3 hours 50 minutes

                                                          Price per night from

                                                          $143

                                                          Distance approx 10.62 km from Madison

                                                            26

                                                            Peace Barn in the heart of the CT River Valley

                                                            Connecticut / Deep River

                                                            Deep River house

                                                            4 10 2 nights min

                                                            • 4 bedrooms
                                                            • sleeps 10
                                                            • 2 nights min
                                                            • Beach / lakeside relaxation
                                                            • Child Friendly
                                                            • Air conditioning

                                                            Price per night from

                                                            $189

                                                            Price per night from

                                                            $189

                                                            Distance approx 15.84 km from Madison

                                                            (4) Excellent 

                                                              17

                                                              Weekly Summer Beach Rental

                                                              Connecticut / Old Lyme

                                                              Old Lyme house

                                                              4 12 7 nights min

                                                              • 4 bedrooms
                                                              • sleeps 12
                                                              • 7 nights min
                                                              • Beach / lakeside relaxation
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $327

                                                              Price per night from

                                                              $327

                                                              Distance approx 10.05 km from Madison

                                                              (5) Excellent 

                                                              Certificate of Excellence

                                                                17

                                                                Two bedroom house with private beach and club within walking distance

                                                                Connecticut / Branford

                                                                Branford house

                                                                2 4 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 4
                                                                • min stay varies
                                                                • Child Friendly
                                                                • Air conditioning
                                                                • Pet Friendly

                                                                Certificate of Excellence

                                                                Price per night from

                                                                $143

                                                                Responds fast!
                                                                avg. 46 minutes

                                                                Price per night from

                                                                $143

                                                                Distance approx 16.8 km from Madison

                                                                (6) Excellent 

                                                                  44

                                                                  Victorian Seasons Stirling

                                                                  North Fork / Greenport

                                                                  Greenport house

                                                                  5 8 2 nights min

                                                                  • 5 bedrooms
                                                                  • sleeps 8
                                                                  • 2 nights min
                                                                  • Nearest beach 1 mi
                                                                  • Child Friendly
                                                                  • Car not necessary

                                                                  Price per night from

                                                                  $971

                                                                  Price per night from

                                                                  $971

                                                                  Distance approx 5.28 km from Madison

                                                                    41

                                                                    New Luxury Waterfront Home

                                                                    Connecticut / Clinton

                                                                    Clinton house

                                                                    4 10 min stay varies

                                                                    • 4 bedrooms
                                                                    • sleeps 10
                                                                    • min stay varies
                                                                    • Beach / lakeside relaxation
                                                                    • Child Friendly
                                                                    • Air conditioning

                                                                    Price per night from

                                                                    $570

                                                                    Responds fast!
                                                                    avg. 54 minutes

                                                                    Price per night from

                                                                    $570

                                                                    Distance approx 17 km from Madison

                                                                    (5) Excellent 

                                                                      39

                                                                      Five Bedroom Italianate Great House - The Gem of East Marion

                                                                      North Fork / East Marion

                                                                      East Marion house

                                                                      5 9 2 nights min

                                                                      • 5 bedrooms
                                                                      • sleeps 9
                                                                      • 2 nights min
                                                                      • Child Friendly
                                                                      • Air conditioning
                                                                      • Private garden

                                                                      Price per night from

                                                                      $1,085

                                                                      Price per night from

                                                                      $1,085

                                                                      Distance approx 18.88 km from Madison

                                                                        24

                                                                        Fabulous Beach Getaway

                                                                        Hamptons / Shelter Island

                                                                        Shelter Island house

                                                                        3 6 min stay varies

                                                                        • 3 bedrooms
                                                                        • sleeps 6
                                                                        • min stay varies
                                                                        • Swimming pool
                                                                        • Ask about children
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $648

                                                                        Price per night from

                                                                        $648

                                                                        Distance approx 19.6 km from Madison

                                                                        (9) Excellent 

                                                                          18

                                                                          Cutchogue Beach Cottage

                                                                          North Fork / Cutchogue

                                                                          Cutchogue cottage

                                                                          2 6 14 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 6
                                                                          • 14 nights min
                                                                          • Beach / lakeside relaxation
                                                                          • Nearest beach 0.1 mi
                                                                          • Child Friendly

                                                                          Price per night from

                                                                          $172

                                                                          Price per night from

                                                                          $172

                                                                          Distance approx 15.91 km from Madison

                                                                          (1) Excellent 

                                                                            19

                                                                            Beautiful Classic North Fork Home, large porch, pool, Jacuzzi, walk to beach

                                                                            North Fork / Southold

                                                                            Southold house

                                                                            3 6 7 nights min

                                                                            • 3 bedrooms
                                                                            • sleeps 6
                                                                            • 7 nights min
                                                                            • Nearest beach 0.8 mi
                                                                            • Swimming pool
                                                                            • Child Friendly

                                                                            Price per night from

                                                                            $457

                                                                            Price per night from

                                                                            $457

                                                                            Distance approx 18.89 km from Madison

                                                                              11

                                                                              Peaceful North Fork Escape - Special Spring and Summer Rates

                                                                              North Fork / Southold

                                                                              Southold house

                                                                              3 5 14 nights min

                                                                              • 3 bedrooms
                                                                              • sleeps 5
                                                                              • 14 nights min
                                                                              • Child Friendly
                                                                              • Air conditioning
                                                                              • Private garden

                                                                              Price per night from

                                                                              $286

                                                                              Price per night from

                                                                              $286