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 54 properties available
BR1 (2)Twin beds, 1st floorBR2 (2)Twin beds, 1st floorBR3 (2)Twin beds, 1st floorHall bath with shower, 1st floorDetached suite:BR4 King en suite with shower, 1st floor
Chappaquiddick
$4,500.00 / per week
Beds 4 beds
Baths 3 Full Bath
Sleeps 8 sleeps
Edgartown Chappaquiddick 337
Chappaquiddick Island on Martha's Vineyard, a charming beach cottage looking out onto amazing views of Edgartown outer harbor. This cottage offers sin... Read More
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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
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BR1 Queen en suite half bath, 1st floorBR2 (1)Twin bed, 1st floor(1) Double, 1st floor,BR3 Double, 1st floorHall bath with shower, 1st floor
Chappaquiddick
$3,300.00 - $3,400.00 / per week
Beds 3 beds
Baths 1 Full, 1 Half Bath
Sleeps 6 sleeps
Rating 5 (2)
Edgartown Chappaquiddick 313
Martha's Vineyard vacation three bedroom cottage by the sea. Located on the south side of Chappaquiddick island, it is adjacent to the Trustees Wasque... Read More
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BR1 King, BR2 Queen, BR3 Queen, BR4 (2)Twin beds, BR5 (2)Twin beds, BR6 (2)Twin beds, BR7 (2)Twin beds, BR8 (2)Twin beds, BR9 (2)Twin beds, BR10 Twin bedHall bath shower and tub, 1st floorHall bath shower and tub, 1st floorHall bath with shower, 2nd floorHall bath with shower, 2nd floorHalf bath, 2nd floorHalf bath, 2nd floor
Chappaquiddick Pet Friendly
$12,000.00 - $16,000.00 / per week
Beds 10 beds
Baths 5 Full, 1 Half Bath
Sleeps 19 sleeps
Edgartown Chappaquiddick 432
Spectacular views with this Chappaquiddick waterfront rental home. Wonderful, spacious old vineyard beach house with private beach and shared tennis c... Read More
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BR1 Queen, en suite, first floor BR2 King, en suite, second floor BR3 King, en suite, second floor BR4 Queen and Twin bunk, en suite BR5 King, en suite.
Hot HOT 13
Chappaquiddick Pet Friendly
$5,000.00 - $23,000.00 / per week
Beds 5 beds
Baths 5 Full, 1 Half Bath
Sleeps 9 sleeps
Edgartown Chappaquiddick 300
Discover the ultimate 5-bedroom, 9-sleeper retreat on Chappaquiddick Island, Martha's Vineyard, where luxury and relaxation converge to redefine your ... Read More
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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
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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 - $6,000.00 / 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
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BR1 Queen, 1st floorBR2 (2)Twin beds, 1st floorHall bath tub and shower, 1st floorBR3 Queen, 2nd floorHall bath with shower, 2nd floorLaundry area, 1st floor
Chappaquiddick Pet Friendly
$5,075.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Edgartown Chappaquiddick 411
This reverse-style three bedroom contemporary home has a welcoming feel the minute you enter the wide foyer. Chappaquiddick is for those who are self-... Read More
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1 2 3 4 5 6 $5075 7
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BR1 King, First Floor BR2 Queen & Trundle with Door to Hall Bath, First FloorHall Bath with Tub/Shower Combo, First Floor BR3 Queen, First Floor BR4 Queen, First Floor BR5 Double Bed Bunk, First Floor Hall Bath with Tub/Shower Combo, First Floor Additional Sleeping, Lower Level
Chappaquiddick
$8,000.00 - $26,500.00 / per week
Beds 5 beds
Baths 2 Full Bath
Sleeps 10 sleeps
Edgartown Chappaquiddick 305
Brand new to the rental market: a new rendition of a classic Chappy home with a private dock and beach access -- renovations include an interior refre... Read More
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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
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BR1 Queen, 1st floorTwin bed in loft area (access by ladder), 2nd floorHall half bath of toilet and sink, 1st floorEnclosed outdoor shower
Chappaquiddick
$2,550.00 - $4,125.00 / per week
Beds 1 beds
Sleeps 3 sleeps
Rating 5 (2)
Edgartown Chappaquiddick 314
Chappy one bedroom guest cottage with access to private beach. Located in close proximity to Chappy ferry and Chappaquiddick community center. No indo... Read More
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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
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
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1 2 3 4 5 6 $3500 7
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