Chappaquiddick

Chappaquiddick, commonly referred to as Chappy, is a small island (about 5 miles long x 3 miles wide) off the eastern end of Edgartown. The mainland of Edgartown and Chappy are sometimes connected, along their southern coast, by a narrow barrier beach only accessible by 4-wheel drive vehicles. The southeastern point of this beach is called Wasque Point – a popular fishing spot especially during the annual Martha's Vineyard Striped Bass and Bluefish Derby held each fall. Chappy boasts numerous wildlife preserves and pristine beaches and offers a more remote, slower pace of life, and yet is just minutes from Edgartown Village. With no commercial center or stores, when one needs or wants to go into town, a bargelike ferry called the On Time shuttles up to three cars, passengers and cyclists to and from the Village. If you feel Chappy checks all the boxes for your summer vacation location, we have a large inventory of homes that includes quaint camps to large waterfront estates.


Properties Available 56 properties available
br>BR2 Queen, 1st floorHall bath with tub/shower, 1st floorBR3 (2)Twin beds, 1st floorSleeper sofa, 2nd floor sun porchHalf bath, 2nd floor
Chappaquiddick
$1,800.00 - $6,825.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 8 sleeps
Edgartown Chappaquiddick 375
Enjoy lovely summer days at this contemporary Chappy home. Reverse level takes full advantage of of the inner harbor views with the kitchen, living, ... Read More
June 2025
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BR1 King, Second FloorHall Bath with Shower Stall, Second FloorBR2 Queen, First FloorHall Bath with Tub Shower Combo, First FloorBR3 (2) Twin Beds, First FloorLaundry, First Floor
Chappaquiddick
$2,000.00 - $4,000.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Rating 5 (1)
Edgartown Chappaquiddick 359
This lovely contemporary Cape offers quiet tranquility yet great proximity to beach, ferry and the Chappaquiddick community center. Spend your days at... Read More
June 2025
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1 2 3 4 5 6 $3000 7
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BR1 King En Suite with Tub/Shower, First FloorQueen & Twin Bed, Second Floor Loft Half Bath, Second Floor Loft
Chappaquiddick
$2,500.00 - $3,000.00 / per week
Beds 2 beds
Baths 1 Full, 1 Half Bath
Sleeps 5 sleeps
Edgartown Chappaquiddick 399
This lovely and well maintained beach house "Seas the Day" is nestled in a private wooded area of Chappaquiddick and is approximately 1.5 miles to Eas... Read More
June 2025
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1 2 3 4 5 6 $2500 7
8 9 10 11 12 13 $3000 14
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BR1 King En Suite with Shower Stall, Second FloorBR2 Queen, First FloorHall Bath with Shower Stall, First FloorBR3 (2) Twin Beds, First FloorLaundry, Lower Level
Chappaquiddick
$3,000.00 - $4,500.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Rating 5 (1)
Edgartown Chappaquiddick 407
Three bedroom chappy cottage, open kitchen, dining, and living area. Two bedrooms on the first floor with access to a hall bathroom. A spacious king s... Read More
June 2025
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1 2 3 4 5 6 $3500 7
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    1 2 3 4 $4500 5
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17 18 19 20 21 22 $4500 23
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BR1 King, 2nd floorHall bath with tub/shower, 2nd floorBR2 2 Twins, 2nd floorBR3 Garage Apartment Queen, en suite shower stall bathroom Main House central ac and Garage bedroom ac mini split
Chappaquiddick Pet Friendly
$3,500.00 - $7,000.00 / per week
Beds 3 beds
Baths 3 Full Bath
Sleeps 6 sleeps
Rating 5 (1)
Edgartown Chappaquiddick 343
Charming Chappaquiddick 2 bedroom 2 full bathroom cottage with additional garage 1 bedroom full bathroom apartment. Main house has central ac througho... Read More
June 2025
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1 2 3 4 5 6 $3500 7
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BR1 Queen, 1st floor, Hall bath with shower, BR2 (2) built in Twin beds, 2nd floor, walk throught to BR3 (2)Twin beds, Hall bathroom with tub only.
Chappaquiddick
$4,200.00 - $7,000.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Rating 5 (1)
Edgartown Chappaquiddick 449
Charming Chappy boathouse rental with views of Edgartown outer harbor. This adorable three bedroom cottage is just minutes to the Chappy ferry if you ... Read More
June 2025
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BR1 Queen, 2nd floorBR2 Queen, 2nd floorBR3 Queen, 2nd floorHall bath with tub/shower, 2nd floorHall bath with tub/shower, 1st floorDetached guesthouse:BR4 (3)Twin beds, (1) Full, and (1) King, 2nd floor loft(No bathroom facilities in guesthouse)
Chappaquiddick
$3,200.00 - $6,500.00 / per week
Beds 4 beds
Baths 2 Full Bath
Sleeps 8 sleeps
Edgartown Chappaquiddick 303
Chappy rental home with front porch and distant views of Katama Bay and South beach. Private setting with a large outdoor deck area for relaxing and e... Read More
June 2025
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1 2 3 4 5 6 $4500 7
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BR1 Queen & Twin, Second FloorBR2 Queen & Twin, Second FloorHall Bath with Shower Stall, Second FloorBR3 Queen, Second FloorBR4 (3) Twin Beds, Second FloorBR5 (2) Twin Trundles, Lower LevelHall Bath with Shower Stall, Lower LevelHall Bath with Tub Shower Combo, First FloorLaundry, Lower Level
Hot HOT 24
Chappaquiddick
$3,200.00 - $4,000.00 / per week
Beds 5 beds
Baths 3 Full Bath
Sleeps 8 sleeps
Edgartown Chappaquiddick 318
An idealistic Chappaquiddick retreat, with all the comforts of home. Private location, great deck area for outdoor entertaining. Room abounds - with ... Read More
June 2025
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1 2 3 4 5 6 $3200 7
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BR1 King, Second FloorBR2 Twin bed, Second FloorQueen in loft areaHall bath with tub/shower, First Floor
Chappaquiddick Pet Friendly
$4,250.00 / per week
Beds 2 beds
Baths 1 Full Bath
Sleeps 5 sleeps
Edgartown Chappaquiddick 434
This Chappaquiddick property offers great access to Katama Bay along with lovely water views. This converted barn includes a large open space in the l... Read More
June 2025
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1 2 3 4 5 6 $4250 7
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BR1 King en suite with separate tub and shower, 2nd floorHalf bath, 2nd floorBR2 Queen en suite with shower, 1st floorBR3 Queen, 1st floorBR4 Double, 1st floorBR5 Double, 1st floorHall bath with shower stall, 1st floorHalf bath, 1st floor
Chappaquiddick
$10,000.00 - $22,000.00 / per week
Beds 5 beds
Baths 3 Full, 1 Half Bath
Sleeps 10 sleeps
Edgartown Chappaquiddick 397
Piece of heaven on Chappy. You will enjoy this property from the moment you enter with a grand view of Katama Bay right from the entrance. Beautiful... Read More
June 2025
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1 2 3 4 5 6 $10000 7
8 9 10 11 12 13 $13000 14
15 16 17 18 19 20 $13000 21
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July 2025
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    1 2 3 4 $13000 5
6 7 8 9 10 11 $13000 12
13 14 15 16 17 18 $22000 19
20 21 22 23 24 25 $22000 26
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August 2025
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          1 $22000 2
3 4 5 6 7 8 $22000 9
10 11 12 13 14 15 $22000 16
17 18 19 20 21 22 $22000 23
24 25 26 27 28 29 $10000 30
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BR1 King En Suite with Shower Stall, First FloorBR2 King En Suite with Shower Stall, First FloorBR3 Queen En Suite with Shower Stall, Second FloorBR4 (2) Twin Beds (extra long) En Suite/Adjoining Hall Bath with Tub Shower Combo, Second FloorPowder Room, First FloorLaundry, First Floor
Chappaquiddick
$5,500.00 - $11,000.00 / per week
Beds 4 beds
Baths 4 Full, 1 Half Bath
Sleeps 8 sleeps
Rating 4.6 (5)
Edgartown Chappaquiddick 358
Chappy at it finest! Newly constructed four bedroom home near Wasque and public trail to the inner harbor. The perfect getaway for your family and f... Read More
June 2025
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1 2 3 4 5 6 $6600 7
8 9 10 11 12 13 $7700 14
15 16 17 18 19 20 $9900 21
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July 2025
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    1 2 3 4 $9900 5
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13 14 15 16 17 18 $9900 19
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3 4 5 6 7 8 $11000 9
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BR1 Queen, 2nd floorHall bath with tub/shower, 2nd floorBR2 Queen, 1st floorBR3 (2)Twin beds, 1st floorHall bath with tub/shower, 1st floor
Chappaquiddick
$2,700.00 - $4,000.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Edgartown Chappaquiddick 493
This Chappy vacation rental is quite affordable and in a fabulous location, close to Wasque beach. This three bedroom reverse-style home offers distan... Read More
June 2025
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          1 $4000 2
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24 25 26 27 28 29 $3600 30
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