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(68)

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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
        Wasque Watch
          7 Bedrooms,
        • 3 Bathrooms
          • , Sleeps 19

        Wasque Watch

        • 7 BR,
        • 3 BA,
        • Sleeps 19
        1. Martha's Vineyard >
        2. Chappaquiddick House
        #3220883
          733-ENJOY BEAUTIFUL WATERVIEWS AND AIR CONDITIONING AT THIS PERFECT SU
            5 Bedrooms, Sleeps 8
          $2,600 - $5,200
          per week

          733-ENJOY BEAUTIFUL WATERVIEWS AND AIR CONDITIONING AT THIS PERFECT SU

          7 night Minimum Stay
          • 5 BR,
          • Sleeps 8
          1. Martha's Vineyard >
          2. Chappaquiddick House
          #3019386
            683 - WONDERFUL COTTAGE STYLE HOME OVERLOOKING LARGE SALT POND
              3 Bedrooms, Sleeps 6
            $1,000 - $2,400
            per week

            683 - WONDERFUL COTTAGE STYLE HOME OVERLOOKING LARGE SALT POND

            5 - 7 night Minimum Stay
            • 3 BR,
            • Sleeps 6
            1. Martha's Vineyard >
            2. Chappaquiddick House
            #3019552
              1555 - COMFORTABLE, WELL MAINTAINED HOME LENDS ITSELF TO A RELAXING VINEYARD VACATION
                3 Bedrooms, Sleeps 6
              $1,200 - $1,800
              per week

              1555 - COMFORTABLE, WELL MAINTAINED HOME LENDS ITSELF TO A RELAXING VINEYARD VACATION

              7 night Minimum Stay
              • 3 BR,
              • Sleeps 6
              1. Martha's Vineyard >
              2. Chappaquiddick House
              #3019532
                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
                  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
                    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)
                      Special Offer $100 Off Our Already Low May & June Rates-MENTION 'VRBO' (May 7 - June 29)
                      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
                                    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
                                      Coastal Contemporary In Katama
                                        5 Bedrooms,
                                      • 5 Bathrooms, 
                                      • 1 Half Bath
                                        • , Sleeps 10
                                      $6,500 - $14,000
                                      per week

                                      Coastal Contemporary In Katama

                                      • 5 BR,
                                      • 5 BA,
                                      • 1 HF BA,
                                      • Sleeps 10
                                      1. Martha's Vineyard >
                                      2. Chappaquiddick House
                                      #3558755
                                        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)
                                          Contemporary Chappy Compound With Pool & Carriage House
                                            5 Bedrooms,
                                          • 4 Bathrooms
                                            • , Sleeps 10
                                          $7,000 - $13,500
                                          per week

                                          Contemporary Chappy Compound With Pool & Carriage House

                                          • 5 BR,
                                          • 4 BA,
                                          • Sleeps 10
                                          1. Martha's Vineyard >
                                          2. Chappaquiddick House
                                          #3244679
                                            Wasque Watch: The Ultimate Island Retreat
                                              10 Bedrooms,
                                            • 5 Bathrooms
                                              • , Sleeps 19
                                            $8,000 - $14,000
                                            per week

                                            Wasque Watch: The Ultimate Island Retreat

                                            • 10 BR,
                                            • 5 BA,
                                            • Sleeps 19
                                            1. Martha's Vineyard >
                                            2. Chappaquiddick Estate
                                            #3244509
                                              Chappy Colonial On Katama Bay
                                                6 Bedrooms,
                                              • 4 Bathrooms
                                                • , Sleeps 12
                                              $5,000 - $7,000
                                              per week

                                              Chappy Colonial On Katama Bay

                                              • 6 BR,
                                              • 4 BA,
                                              • Sleeps 12
                                              1. Martha's Vineyard >
                                              2. Chappaquiddick House
                                              #3247499
                                                Chappy Beach House With Guest Cottage & Water Views
                                                  5 Bedrooms,
                                                • 3 Bathrooms
                                                  • , Sleeps 8
                                                $2,600 - $5,200
                                                per week

                                                Chappy Beach House With Guest Cottage & Water Views

                                                • 5 BR,
                                                • 3 BA,
                                                • Sleeps 8
                                                1. Martha's Vineyard >
                                                2. Chappaquiddick House
                                                #3482062
                                                  Manaca Hill Beach Getaway With Water Views
                                                    1 Bedrooms,
                                                  • 2 Bathrooms
                                                    • , Sleeps 6
                                                  $1,800 - $2,650
                                                  per week

                                                  Manaca Hill Beach Getaway With Water Views

                                                  • 1 BR,
                                                  • 2 BA,
                                                  • Sleeps 6
                                                  1. Martha's Vineyard >
                                                  2. Chappaquiddick House
                                                  #3482061
                                                    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
                                                      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
                                                          Vintage Waterfront Home On Chappy's Snow Point
                                                            6 Bedrooms,
                                                          • 4 Bathrooms
                                                            • , Sleeps 13
                                                          $8,000 - $10,000
                                                          per week

                                                          Vintage Waterfront Home On Chappy's Snow Point

                                                          • 6 BR,
                                                          • 4 BA,
                                                          • Sleeps 13
                                                          1. Martha's Vineyard >
                                                          2. Chappaquiddick House
                                                          #3244617
                                                            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
                                                              • 1 - 30 of 68
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