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(78)

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Calm, Serene, elegant, Indoor Lap pool, Chappaquiddick
    3 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 8
$3,000 - $4,500
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
                        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
                          Classic Colonial With Views Of Edgartown Harbor & Lighthouse
                            3 Bedrooms,
                          • 3 Bathrooms
                            • , Sleeps 8
                          $6,000 - $15,000
                          per week

                          Classic Colonial With Views Of Edgartown Harbor & Lighthouse

                          • 3 BR,
                          • 3 BA,
                          • Sleeps 8
                          1. Martha's Vineyard >
                          2. Chappaquiddick House
                          #3564046
                            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
                            #3564199
                              Idyllic Katama Retreat With Vineyard Charm
                                3 Bedrooms,
                              • 2 Bathrooms, 
                              • 1 Half Bath
                                • , Sleeps 10
                              $2,500 - $3,600
                              per week

                              Idyllic Katama Retreat With Vineyard Charm

                              • 3 BR,
                              • 2 BA,
                              • 1 HF BA,
                              • Sleeps 10
                              1. Martha's Vineyard >
                              2. Chappaquiddick House
                              #3564285
                                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
                                #3564283
                                  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
                                  #3564300
                                    Katama Bay House: Waterfront Views And Private Beach
                                      4 Bedrooms,
                                    • 4 Bathrooms, 
                                    • 1 Half Bath
                                      • , Sleeps 8
                                    $6,500 - $9,000
                                    per week

                                    Katama Bay House: Waterfront Views And Private Beach

                                    • 4 BR,
                                    • 4 BA,
                                    • 1 HF BA,
                                    • Sleeps 8
                                    1. Martha's Vineyard >
                                    2. Chappaquiddick House
                                    #3564118
                                      Katama Contemporary With Pool And Large Private Yard
                                        3 Bedrooms,
                                      • 2 Bathrooms
                                        • , Sleeps 8
                                      $5,000
                                      per week

                                      Katama Contemporary With Pool And Large Private Yard

                                      • 3 BR,
                                      • 2 BA,
                                      • Sleeps 8
                                      1. Martha's Vineyard >
                                      2. Chappaquiddick House
                                      #3564182
                                        Edgartown Lighthouse & Harbor View: Gambrel With Guest Cottage
                                          4 Bedrooms,
                                        • 4 Bathrooms, 
                                        • 1 Half Bath
                                          • , Sleeps 8
                                        $12,000
                                        per week

                                        Edgartown Lighthouse & Harbor View: Gambrel With Guest Cottage

                                        • 4 BR,
                                        • 4 BA,
                                        • 1 HF BA,
                                        • Sleeps 8
                                        1. Martha's Vineyard >
                                        2. Chappaquiddick House
                                        #3564057
                                          Classic 1930's Beachfront Home With Dock and Private Beach
                                            8 Bedrooms,
                                          • 5 Bathrooms, 
                                          • 1 Half Bath
                                            • , Sleeps 14
                                          $12,000 - $18,000
                                          per week

                                          Classic 1930's Beachfront Home With Dock and Private Beach

                                          • 8 BR,
                                          • 5 BA,
                                          • 1 HF BA,
                                          • Sleeps 14
                                          1. Martha's Vineyard >
                                          2. Chappaquiddick House
                                          #3564180
                                            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
                                            #3564281
                                              Captain's Home On Edgartown Harbor
                                                6 Bedrooms,
                                              • 3 Bathrooms, 
                                              • 1 Half Bath
                                                • , Sleeps 12
                                              $7,500 - $16,000
                                              per week

                                              Captain's Home On Edgartown Harbor

                                              • 6 BR,
                                              • 3 BA,
                                              • 1 HF BA,
                                              • Sleeps 12
                                              1. Martha's Vineyard >
                                              2. Chappaquiddick House
                                              #3564041
                                                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)
                                                  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
                                                  #3564035
                                                    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
                                                    #3564257
                                                      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
                                                        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
                                                          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
                                                          #3564143
                                                            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
                                                              • 1 - 30 of 78
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