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, 1st floorBR2 (2)Twin beds, 1st floorHall bath with shower stall, 1st floor
Chappaquiddick
$2,650.00 - $3,995.00 / per week
Beds 2 beds
Baths 1 Full Bath
Sleeps 4 sleeps
Edgartown Chappaquiddick 386
Lovely two bedroom cottage on Chappaquiddick with association water access at the end of the road and close proximity to Wasque beach. From the momen... Read More
June 2025
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1 2 3 4 5 6 $2900 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
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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
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 King En Suite with Tub & Shower Stall, First FloorBR2 King En Suite with Shower Stall, Second FloorBR3 Double, Second FloorHall Bath with Tub & Shower Stall, Second FloorBR4 (2) Twin Beds, Second FloorPowder Room, First FloorLaundry, First Floor
Chappaquiddick
$6,500.00 - $9,500.00 / per week
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps 8 sleeps
Edgartown Chappaquiddick 330
This stunning Chappy vacation rental offers four bedrooms and central air conditioning. Once you disembark from the "on time" chappy ferry you enter a... Read More
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1 2 3 4 5 6 $6500 7
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15 16 17 18 19 20 $8900 21
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BR1 King, Second FloorBR2 Twin bed, Second FloorQueen in loft areaHall bath with tub/shower, First Floor
Hot HOT 12
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 Queen, lower levelHall bath tub/shower, lower levelBR2 (2)Twin beds, lower levelBR3 Queen, lower levelBR4 Queen, lower levelHall bath with shower & laundry area, lower levelHalf bath, 1st floor
Chappaquiddick
$1,900.00 - $4,900.00 / per week
Beds 4 beds
Baths 2 Full, 1 Half Bath
Sleeps 8 sleeps
Rating 5 (1)
Edgartown Chappaquiddick 331
Chappaquiddick four bedroom reverse-style home, accentuating the breathtaking views of Katama Bay and the ocean. An outdoor deck on the upper living a... Read More
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Boathouse:BR1 King, 1st floorHall bath with shower, 1st floor(2)Twin beds and Queen on second floor landing (pass-through to BR2)BR2 Queen, en-suite half bath 2nd floorHall bath with tub/shower, 2nd floorA-Frame:BR1 King and (2)Twin beds, 2nd floor (twins in oversized dormer closet)Hall bath with tub/shower, 2nd floor
Chappaquiddick
$10,000.00 - $12,000.00 / per week
Beds 3 beds
Baths 3 Full, 1 Half Bath
Sleeps 11 sleeps
Rating 5 (1)
Edgartown Chappaquiddick 311
Chappaquiddick waterfront with a dock! Two stunning cottages rent together on the inner harbor, The Boathouse and A-Frame. Your dream come true with ... Read More
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BR1 Double and Bunk bed, 1st floorBR2 Queen with half bath, 1st floorBR3 Queen, 1st floorHall bath with shower stall, 1st floor
Chappaquiddick Pet Friendly
$2,500.00 - $4,000.00 / per week
Beds 3 beds
Baths 1 Full, 1 Half Bath
Sleeps 6 sleeps
Rating 5 (4)
Edgartown Chappaquiddick 323
Chappaquiddick on Martha's Vineyard, amazing single level cottage lovingly renovated to make your stay more comfortable and enjoyable. Updated applian... Read More
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1 2 3 4 5 6 $3000 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, 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.
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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1 2 3 4 5 6 $8000 7
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24 25 26 27 28 29 $12000 30
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BR1 King en suite with shower, 1st floor (with sliders to deck)BR2 Bunk bed & Twin bed, 1st floorBR3 Queen, 1st floorHall bath with tub/shower, 1st floorHall bath with tub/shower, 1st floorQueen Bed is a pass thru room to BR1
Hot HOT 13
Chappaquiddick Pet Friendly
$3,100.00 - $5,900.00 / per week
Beds 3 beds
Baths 3 Full Bath
Sleeps 8 sleeps
Rating 4 (1)
Edgartown Chappaquiddick 408
Spectacular 180 degree views, set up high overlooking Cape Pogue. This three bedroom pet friendly single level home with wonderful views. Features an ... Read More
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