Choose Chappaquiddick Rentals for Charming Memories

Though Chappaquiddick Island, a sleepy little village on Martha's Vineyard in Massachusetts may be more well-known for the tragedy involving Senator Ted Kennedy in 1969, it is a great destination for visitors. Chappaquiddick Island is located within Edgartown, the county seat, and was once connected by a large sandbar that has since been diminished by storms. To this day, Chappaquiddick rentals are in high demand and provide some of the most memorable vacations for the whole family.

Chappaquiddick Cottages Are Homes away from Home


Chappaquiddick vacation rentals are set within a picturesque little village surrounded by the natural beauty of the island. Because the island is home to beautiful beaches and soothing seas, Chappaquiddick cottages provide the perfect homes away from home within a perfect seaside setting. Visitors can enjoy shopping for produce, fine cheeses, and fresh seafood at the local markets to enjoy dinners at their Chappaquiddick rentals.

Bike through Town from Chappaquiddick Vacation Rentals


Though swimming and sand are much loved by those staying in Chappaquiddick vacation rentals, there is much more fun to be had on the island. Renting bicycles is a great way to not only get around town, but to see the gorgeous natural landscaping and beautiful vacation homes. Riding bikes from Chappaquiddick cottages to the local beaches can be fun for the whole family. Just remember to pack a picnic basket for lunch!

Chappaquiddick Rentals Let You Fish All Day


Fishing is also a fun way to spend the time at Chappaquiddick rentals. In the fall in particular, Wasque Point is a great location to make that perfect catch for dinner! If you prefer to fish from a boat, there are plenty of charters available near all Chappaquiddick vacation rentals. You can spend a full or half-day out on the high seas catching fish and having fun and return to Chappaquiddick cottages to prepare your catch for dinner.

Increase your search options for Martha's Vineyard lodging in the following areas: Chilmark beach rentals, lodging in Edgartown MA, Katama beach homes, Vineyard Haven home rental, or vacation accommodation West Tisbury MA.



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Chappaquiddick: Houses, Cottages & More(59)

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Calm, Serene, elegant, Indoor Lap pool, Chappaquiddick
    3 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 8
$3,000 - $5,500
per week

Calm, Serene, elegant, Indoor Lap pool, Chappaquiddick

7 night Minimum Stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
  1. Martha's Vineyard >
  2. Chappaquiddick House
#238889
    Luxury Chappaquiddick Family Home Heated pool, tennis court, jacuzzi
      4 Bedrooms,
    • 4 Bathrooms
      • , Sleeps 14
    $7,000 - $15,000
    per week

    Luxury Chappaquiddick Family Home Heated pool, tennis court, jacuzzi

    7 night Minimum Stay
    • 4 BR,
    • 4 BA,
    • Sleeps 14
    1. Martha's Vineyard >
    2. Chappaquiddick House
    #921866
      Sweet Summer Escape...NO PETS/NO SMOKING
        3 Bedrooms,
      • 1 Bathroom, 
      • 1 Half Bath
        • , Sleeps 8

      Sweet Summer Escape...NO PETS/NO SMOKING

      • 3 BR,
      • 1 BA,
      • 1 HF BA,
      • Sleeps 8
      1. Martha's Vineyard >
      2. Chappaquiddick Cottage
      #105878
        2 Reviews
        SPECTAC-OCEANVU HOME**BEST CHAPPY LOCATION *APRIL/MAY/JUNE-LOW RATES**
          4 Bedrooms,
        • 2 Bathrooms, 
        • 1 Half Bath
          • , Sleeps 8
        $222 - $500
        per night

        SPECTAC-OCEANVU HOME**BEST CHAPPY LOCATION *APRIL/MAY/JUNE-LOW RATES**

        2 - 7 night Minimum Stay
        • 4 BR,
        • 2 BA,
        • 1 HF BA,
        • Sleeps 8
        1. Martha's Vineyard >
        2. Chappaquiddick House
        #105250
          (16)
          Edg.Harbor/Ocean Views, Walk to Town or Private 3 Acre Beach (below).
            3 Bedrooms,
          • 2 Bathrooms
            • , Sleeps 8
          $1,800 - $3,600
          per week

          Edg.Harbor/Ocean Views, Walk to Town or Private 3 Acre Beach (below).

          7 - 14 night Minimum Stay
          • 3 BR,
          • 2 BA,
          • Sleeps 8
          1. Martha's Vineyard >
          2. Chappaquiddick House
          #105245
            Lovely Chappaquiddick Cape
              4 Bedrooms,
            • 2 Bathrooms
              • , Sleeps 8
            $1,960
            per week

            Lovely Chappaquiddick Cape

            7 night Minimum Stay
            • 4 BR,
            • 2 BA,
            • Sleeps 8
            1. Martha's Vineyard >
            2. Chappaquiddick House
            #121311
              Bright, Airy Chappy Home Near Wasque Reservation
                2 Bedrooms,
              • 1 Bathroom, 
              • 1 Half Bath
                • , Sleeps 6
              $200 - $250
              per night

              Bright, Airy Chappy Home Near Wasque Reservation

              3 - 7 night Minimum Stay
              • 2 BR,
              • 1 BA,
              • 1 HF BA,
              • Sleeps 6
              1. Martha's Vineyard >
              2. Chappaquiddick House
              #275327
                (3)
                219 - Beautiful Waterfront Home On Chappaquiddick
                  5 Bedrooms,
                • 2 Bathrooms
                  • , Sleeps 2
                $2,500 - $6,000
                per week

                219 - Beautiful Waterfront Home On Chappaquiddick

                5 - 7 night Minimum Stay
                • 5 BR,
                • 2 BA,
                • Sleeps 2
                1. Martha's Vineyard >
                2. Chappaquiddick Studio
                #3476552
                  Charming Chappy Contemporary-Chappaquiddick Island
                    4 Bedrooms,
                  • 2 Bathrooms
                    • , Sleeps 8
                  $1,150 - $2,600
                  per week

                  Charming Chappy Contemporary-Chappaquiddick Island

                  7 night Minimum Stay
                  • 4 BR,
                  • 2 BA,
                  • Sleeps 8
                  1. Martha's Vineyard >
                  2. Chappaquiddick House
                  #120466
                    Lovely Chappy Cape - Chappaquiddick Island
                      3 Bedrooms,
                    • 1 Bathroom
                      • , Sleeps 6
                    $1,150 - $1,960
                    per week

                    Lovely Chappy Cape - Chappaquiddick Island

                    7 night Minimum Stay
                    • 3 BR,
                    • 1 BA,
                    • Sleeps 6
                    1. Martha's Vineyard >
                    2. Chappaquiddick House
                    #120465
                      Edgartown, Chappaquiddick 4 Bedroom 2 Bath, 1 Mile from Ferry
                        4 Bedrooms,
                      • 2 Bathrooms
                        • , Sleeps 8
                      $275 - $295
                      per night

                      Edgartown, Chappaquiddick 4 Bedroom 2 Bath, 1 Mile from Ferry

                      2 night Minimum Stay
                      • 4 BR,
                      • 2 BA,
                      • Sleeps 8
                      1. Martha's Vineyard >
                      2. Chappaquiddick House
                      #396966
                        Chappaquiddick Island beach house
                          3 Bedrooms,
                        • 1 Bathroom, 
                        • 1 Half Bath
                          • , Sleeps 6
                        $2,100 - $2,400
                        per week

                        Chappaquiddick Island beach house

                        7 night Minimum Stay
                        • 3 BR,
                        • 1 BA,
                        • 1 HF BA,
                        • Sleeps 6
                        1. Martha's Vineyard >
                        2. Chappaquiddick House
                        #134239
                          1 Review
                          Beautiful Wasque Waterview
                            3 Bedrooms,
                          • 2 Bathrooms
                            • , Sleeps 6
                          $500
                          per night

                          Beautiful Wasque Waterview

                          2 - 3 night Minimum Stay
                          • 3 BR,
                          • 2 BA,
                          • Sleeps 6
                          1. Martha's Vineyard >
                          2. Chappaquiddick House
                          #104816
                            Oceanviews, Walk to Beaches, Nature Preserves
                              4 Bedrooms,
                            • 2 Bathrooms
                              • , Sleeps 10
                            $1,100 - $2,900
                            per week

                            Oceanviews, Walk to Beaches, Nature Preserves

                            5 - 7 night Minimum Stay
                            • 4 BR,
                            • 2 BA,
                            • Sleeps 10
                            1. Martha's Vineyard >
                            2. Chappaquiddick House
                            #105744
                              (8)
                              Adorable Chappy Getaway
                                2 Bedrooms,
                              • 1 Bathroom
                                • , Sleeps 4
                              $1,400 - $1,799
                              per week

                              Adorable Chappy Getaway

                              7 night Minimum Stay
                              • 2 BR,
                              • 1 BA,
                              • Sleeps 4
                              1. Martha's Vineyard >
                              2. Chappaquiddick Cottage
                              #985053
                                413-SEA AIR, OCEAN BEACH & NATURE PRESERVE -ALL CONDUCIVE TO RELAXING
                                  4 Bedrooms, Sleeps 10
                                $1,200 - $3,200
                                per week

                                413-SEA AIR, OCEAN BEACH & NATURE PRESERVE -ALL CONDUCIVE TO RELAXING

                                7 night Minimum Stay
                                • 4 BR,
                                • Sleeps 10
                                1. Martha's Vineyard >
                                2. Chappaquiddick House
                                #3485191
                                  722 - CLASSIC VINEYARD CAPE WITH GLORIOUS BEACH
                                    4 Bedrooms, Sleeps 10
                                  $1,350 - $2,975
                                  per week

                                  722 - CLASSIC VINEYARD CAPE WITH GLORIOUS BEACH

                                  5 - 7 night Minimum Stay
                                  • 4 BR,
                                  • Sleeps 10
                                  1. Martha's Vineyard >
                                  2. Chappaquiddick House
                                  #3483170
                                    Wasque Watch
                                      7 Bedrooms,
                                    • 3 Bathrooms
                                      • , Sleeps 19

                                    Wasque Watch

                                    • 7 BR,
                                    • 3 BA,
                                    • Sleeps 19
                                    1. Martha's Vineyard >
                                    2. Chappaquiddick House
                                    #3220883
                                      1452 - Beautiful Chappaquiddick Home with Pool
                                        5 Bedrooms,
                                      • 4 Bathrooms
                                        • , Sleeps 10
                                      $8,000 - $16,000
                                      per week

                                      1452 - Beautiful Chappaquiddick Home with Pool

                                      5 - 7 night Minimum Stay
                                      • 5 BR,
                                      • 4 BA,
                                      • Sleeps 10
                                      1. Martha's Vineyard >
                                      2. Chappaquiddick House
                                      #3019399
                                        The perfect spot in chappaquiddick near the ocean, relaxing and secluded.
                                          4 Bedrooms,
                                        • 2 Bathrooms
                                          • , Sleeps 6
                                        $1,500 - $1,800
                                        per week

                                        The perfect spot in chappaquiddick near the ocean, relaxing and secluded.

                                        7 night Minimum Stay
                                        • 4 BR,
                                        • 2 BA,
                                        • Sleeps 6
                                        1. Martha's Vineyard >
                                        2. Chappaquiddick House
                                        #270862
                                          526 - STEP BACK IN TIME COTTAGE WITH LOVELY BEACH!
                                            3 Bedrooms, Sleeps 6
                                          $1,000 - $1,450
                                          per week

                                          526 - STEP BACK IN TIME COTTAGE WITH LOVELY BEACH!

                                          5 - 7 night Minimum Stay
                                          • 3 BR,
                                          • Sleeps 6
                                          1. Martha's Vineyard >
                                          2. Chappaquiddick House
                                          #3019546
                                            1 Review
                                            259-WONDERFUL OLD VINEYARD SUMMER HOME ON 88 ACRES
                                              10 Bedrooms,
                                            • 2 Half Baths
                                              • , Sleeps 19
                                            $4,900 - $10,395
                                            per week

                                            259-WONDERFUL OLD VINEYARD SUMMER HOME ON 88 ACRES

                                            5 - 7 night Minimum Stay
                                            • 10 BR,
                                            • 2 HF BA,
                                            • Sleeps 19
                                            1. Martha's Vineyard >
                                            2. Chappaquiddick House
                                            #3019314
                                              615 - ICED TEA IN A VICTORIAN TOWER -NOW THERE'S THE ESSENCE OF A BYGONE SUMMER ERA WAITING FOR YOU!
                                                10 Bedrooms,
                                              • 1 Bathroom, 
                                              • 2 Half Baths
                                                • , Sleeps 19
                                              $8,250 - $14,000
                                              per week

                                              615 - ICED TEA IN A VICTORIAN TOWER -NOW THERE'S THE ESSENCE OF A BYGONE SUMMER ERA WAITING FOR YOU!

                                              7 night Minimum Stay
                                              • 10 BR,
                                              • 1 BA,
                                              • 2 HF BA,
                                              • Sleeps 19
                                              1. Martha's Vineyard >
                                              2. Chappaquiddick House
                                              #3019289
                                                618 - CHAPPAQUIDDICK CONTEMPORARY WITH 270 DEGREE WATERVIEWS AND STEPS TO A PRIVATE BEACH
                                                  3 Bedrooms, Sleeps 8
                                                $1,500 - $3,600
                                                per week

                                                618 - CHAPPAQUIDDICK CONTEMPORARY WITH 270 DEGREE WATERVIEWS AND STEPS TO A PRIVATE BEACH

                                                5 - 7 night Minimum Stay
                                                • 3 BR,
                                                • Sleeps 8
                                                1. Martha's Vineyard >
                                                2. Chappaquiddick House
                                                #3019518
                                                  280 - BRIGHT, LIGHT AND AIRY HOME SURROUNDED BY LOVELY FLOWER GARDENS
                                                    4 Bedrooms, Sleeps 8
                                                  $2,200 - $4,000
                                                  per week

                                                  280 - BRIGHT, LIGHT AND AIRY HOME SURROUNDED BY LOVELY FLOWER GARDENS

                                                  7 night Minimum Stay
                                                  • 4 BR,
                                                  • Sleeps 8
                                                  1. Martha's Vineyard >
                                                  2. Chappaquiddick House
                                                  #3019509
                                                    1578 - WATERFRONT,VINTAGE VINEYARD WITH MODERN CONVENIENCES!
                                                      4 Bedrooms, Sleeps 8
                                                    $4,500 - $5,000
                                                    per week

                                                    1578 - WATERFRONT,VINTAGE VINEYARD WITH MODERN CONVENIENCES!

                                                    7 - 14 night Minimum Stay
                                                    • 4 BR,
                                                    • Sleeps 8
                                                    1. Martha's Vineyard >
                                                    2. Chappaquiddick House
                                                    #3019320
                                                      407 - SET AMOUNG THE TREETOPS ON CHAPPAQUIDDICK'S HIGHEST POINT WITH LOVELY DISTANT VIEWS OF THE OCEAN
                                                        3 Bedrooms, Sleeps 6
                                                      $1,500 - $2,700
                                                      per week

                                                      407 - SET AMOUNG THE TREETOPS ON CHAPPAQUIDDICK'S HIGHEST POINT WITH LOVELY DISTANT VIEWS OF THE OCEAN

                                                      5 - 7 night Minimum Stay
                                                      • 3 BR,
                                                      • Sleeps 6
                                                      1. Martha's Vineyard >
                                                      2. Chappaquiddick House
                                                      #3019514
                                                        294 - CLASSIC CHAPPAQUIDDICK W/WAFTING SEA BREEZES
                                                          7 Bedrooms,
                                                        • 2 Half Baths
                                                          • , Sleeps 12
                                                        $3,250 - $5,750
                                                        per week

                                                        294 - CLASSIC CHAPPAQUIDDICK W/WAFTING SEA BREEZES

                                                        7 night Minimum Stay
                                                        • 7 BR,
                                                        • 2 HF BA,
                                                        • Sleeps 12
                                                        1. Martha's Vineyard >
                                                        2. Chappaquiddick House
                                                        #3019346
                                                          1450 - BEAUTIFUL WATERFRONT ISLAND HOME WITH VIEWS OF KATAMA BAY
                                                            6 Bedrooms,
                                                          • 1 Bathroom
                                                            • , Sleeps 10
                                                          $5,500 - $7,000
                                                          per week

                                                          1450 - BEAUTIFUL WATERFRONT ISLAND HOME WITH VIEWS OF KATAMA BAY

                                                          7 night Minimum Stay
                                                          • 6 BR,
                                                          • 1 BA,
                                                          • Sleeps 10
                                                          1. Martha's Vineyard >
                                                          2. Chappaquiddick House
                                                          #3019329
                                                            1435 - LOVELY HOME ON CHAPPAQUIDDICK WITH WATERVIEWS OF THE SOUND
                                                              3 Bedrooms,
                                                            • 2 Bathrooms
                                                              • , Sleeps 5
                                                            $1,400 - $2,200
                                                            per week

                                                            1435 - LOVELY HOME ON CHAPPAQUIDDICK WITH WATERVIEWS OF THE SOUND

                                                            5 - 7 night Minimum Stay
                                                            • 3 BR,
                                                            • 2 BA,
                                                            • Sleeps 5
                                                            1. Martha's Vineyard >
                                                            2. Chappaquiddick House
                                                            #3019504
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