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 55 properties available
BR1 Queen, Second FloorHall Bath with Shower Stall, Second FloorBR2 (2) Twin Beds, Second FloorHall Bath with Tub Shower Combo, First Floor
Chappaquiddick
$2,100.00 - $2,882.00 / per week
Beds 2 beds
Baths 2 Full Bath
Sleeps 4 sleeps
Edgartown Chappaquiddick 325
This lovely and well maintained two bedroom cape is nestled in an attractive wooded area of Chappaquiddick. Convenient location, approximately 1.5 mil... Read More
June 2025
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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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BR1 King en suite with shower, 1st floorBR2 King en suite with tub/shower, 1st floorQueen bed, 2nd floor loftHalf bath, 1st floorLaundry, 1st floorGuest house: BR3 Queen, 1st floorBR4 Queen, 1st floorHall bath with tub/shower, 1st floor
Chappaquiddick Pet Friendly
$3,600.00 - $8,250.00 / per week
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps 10 sleeps
Rating 4.3 (3)
Edgartown Chappaquiddick 396
Custom Chappaquiddick contemporary, with separate guest house, nestled on three wooded acres. Located far enough from the main road to be quiet and r... Read More
June 2025
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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 & 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
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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BR1 Queen En Suite with Shower Stall, First FloorBR2 Queen En Suite with Shower Tub Combo, Second FloorLaundry Facilities and Powder Room, First Floor
Chappaquiddick Pet Friendly
$4,500.00 / per week
Beds 2 beds
Baths 2 Full, 1 Half Bath
Sleeps 4 sleeps
Edgartown Chappaquiddick 435
Easy to access, "Retreat House", a two-bedroom guest house, is nestled between Chappaquiddick's paved road and the waterfront. Enjoy the sweeping ocea... Read More
June 2025
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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
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
June 2025
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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 (2)
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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Main House:BR1 King En Suite with Shower Stall (Door to Hallway as well), First FloorHall Bath with Shower Stall, Second FloorGarage Apartment (connected through breezeway from kitchen):BR2 Queen, Second FloorHall Bath with Shower Stall, Second FloorBR3 (2) Queen Beds, Second FloorBR4 (2) Double Beds, Second Floor
Chappaquiddick
$7,000.00 - $15,000.00 / per week
Beds 4 beds
Baths 3 Full Bath
Sleeps 8 sleeps
Edgartown Chappaquiddick 357
This spacious four-bedroom home is the ultimate Chappaquiddick vacation retreat. Designed in a reverse-style layout, it features an open-concept secon... Read More
June 2025
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1 2 3 4 5 6 $7000 7
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BR1 King, 1st floorBR2 (2)Twin beds, 1st floorBR3 (2)Twin beds, 2nd floorBR4 Double bed, 2nd floorBR5 Queen, 2nd floorHall bath with tub and shower, 1st floorHall bath with shower, 2nd floor
Chappaquiddick Pet Friendly
$6,000.00 / per week
Beds 5 beds
Baths 2 Full Bath
Sleeps 11 sleeps
Rating 5 (1)
Edgartown Chappaquiddick 433
Spectacular Chappaquiddick rental property with great views and access to Katama Bay. Lovely five bedroom, old farmhouse full of charm, a screened por... Read More
June 2025
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24 25 26 27 28 29 $6000 30
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BR1 Queen with water views, 1st floorBR2 (2)Twin beds, 2nd floor (accessed via spiral staircase)Hall bath with shower & laundry, 1st floor A/C Wall Unit in each bedroom
Chappaquiddick Pet Friendly
$2,000.00 - $4,000.00 / per week
Beds 2 beds
Baths 1 Full Bath
Sleeps 4 sleeps
Rating 5 (1)
Edgartown Chappaquiddick 327
2 week minimum. A cottage by the bay... pulled from the pages of a seaside novel. This charming two-bedroom home has been renovated and fully updated... Read More
June 2025
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1 2 3 4 5 6 $4000 7
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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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