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 Queen en suite with shower, 1st floor (access to first floor deck)BR2 King en suite with shower, 2nd floorBR3 (2)Twin beds (with 3/4 interior wall), 2nd floorBR4 (2)Twin beds (with 3/4 interior wall), 2nd floorHall bath with tub/shower, 2nd floor2nd floor bedrooms with balconies
Chappaquiddick
$6,500.00 - $9,000.00 / per week
Beds 4 beds
Baths 3 Full Bath
Sleeps 8 sleeps
Rating 5 (2)
Edgartown Chappaquiddick 395
Chappy four bedroom contemporary with distant water views and access to Katama Bay is a wonderful retreat for all to experience. An added bonus is the... Read More
June 2025
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1 2 3 4 5 6 $7000 7
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22 23 24 25 26 27 $8000 28
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13 14 15 16 17 18 $8000 19
20 21 22 23 24 25 $9000 26
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10 11 12 13 14 15 $9000 16
17 18 19 20 21 22 $9000 23
24 25 26 27 28 29 $6500 30
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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
June 2025
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1 2 3 4 5 6 $12000 7
8 9 10 11 12 13 $12000 14
15 16 17 18 19 20 $12000 21
22 23 24 25 26 27 $16000 28
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24 25 26 27 28 29 $16000 30
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BR1 Double, 1st floorBR2 Bunk Beds, (1) Twin, 1st floorHall bath with tub/shower, 1st floorBR3 Queen with Sitting Area, 2nd floorBR4 (3)Twin Beds, 2nd floorHall Bath with tub/shower
Hot HOT 29
Chappaquiddick Pet Friendly
$2,355.00 - $3,825.00 / per week
Beds 4 beds
Baths 2 Full Bath
Sleeps 10 sleeps
Edgartown Chappaquiddick 342
This classic, Cape-Style Chappaquiddick home has room for the whole family! With 4 bedrooms and 2 bathrooms, this property sleeps 10 comfortably. Ente... Read More
June 2025
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10 11 12 13 14 15 $3825 16
17 18 19 20 21 22 $3825 23
24 25 26 27 28 29 $3825 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
Hot HOT 22
Chappaquiddick Pet Friendly
$2,000.00 - $5,000.00 / 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 $5000 7
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15 16 17 18 19 20 $5000 21
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July 2025
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    1 2 3 4 $5000 5
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13 14 15 16 17 18 $5000 19
20 21 22 23 24 25 $5000 26
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3 4 5 6 7 8 $5000 9
10 11 12 13 14 15 $5000 16
17 18 19 20 21 22 $5000 23
24 25 26 27 28 29 $5000 30
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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
8 9 10 11 12 13 $5000 14
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10 11 12 13 14 15 $6500 16
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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
Hot HOT 25
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 waterfront rental property with great views of Katama Bay. Lovely five bedroom, old farmhouse full of charm, a screened por... Read More
June 2025
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1 2 3 4 5 6 $6000 7
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22 23 24 25 26 27 $6000 28
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Main house:BR1 King en suite separate tub and shower, 1st floorBR2 Queen en suite tub/shower, 1st floorBR3 King or (2)Twin beds en suite with tub/shower, 1st floor BR4 Den or (2)Twin beds en suite with tub/shower, 1st floorHalf bath, 2nd floorGuesthouse:BR5 Queen, 1st floorBR6 (2)Bunk beds, 1st floorHall bath with shower, 1st floor
Chappaquiddick Pet Friendly
$18,725.00 - $25,000.00 / per week
Beds 6 beds
Baths 5 Full, 1 Half Bath
Sleeps 14 sleeps
Edgartown Chappaquiddick 398
This property is set in a wonderfully remote and private area of Chappaquiddick, yet only two miles to the Chappy ferry. Both the main and guesthouse ... Read More
June 2025
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1 2 3 4 5 6 $25000 7
8 9 10 11 12 13 $25000 14
15 16 17 18 19 20 $25000 21
22 23 24 25 26 27 $25000 28
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    1 2 3 4 $25000 5
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13 14 15 16 17 18 $25000 19
20 21 22 23 24 25 $25000 26
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17 18 19 20 21 22 $18725 23
24 25 26 27 28 29 $18725 30
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BR1 Queen, 1st floorBR2 Queen, 1st floorBR3 Twin trundle bed, 1st floorHall bath with tub/shower, 1st floorHall bath with shower stall, 1st floor
Chappaquiddick Pet Friendly
$2,000.00 - $2,250.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Edgartown Chappaquiddick 485
Chappy charmer. This Chappaquiddick three bedroom vacation rental brings you back to the basics. Simplistic living all on one level, with an enclosed ... 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
June 2025
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1 2 3 4 5 6 $6500 7
8 9 10 11 12 13 $6500 14
15 16 17 18 19 20 $8900 21
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BR1 King, Second FloorHall Bath with Tub Shower Combo, Second FloorOverflow (2) Twin Beds, Second FloorOverflow Double, Second Floor LoftHall Bath with Tub Shower Combo, First FloorBR2 Queen, GuesthouseBR3 (2) Twin Beds, GuesthouseHall Bath with Shower Stall, Guesthouse
Chappaquiddick Pet Friendly
$5,000.00 - $7,875.00 / per week
Beds 3 beds
Baths 3 Full Bath
Sleeps 9 sleeps
Edgartown Chappaquiddick 387
This five bedroom home is truly a quintessential Chappy retreat. Set in the woods, this property offers privacy and a beautiful distant view of Edgart... Read More
June 2025
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24 25 26 27 28 29 $7875 30
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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
Hot HOT 13
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
June 2025
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1 2 3 4 5 6 $5075 7
8 9 10 11 12 13 $5075 14
15 16 17 18 19 20 $5075 21
22 23 24 25 26 27 $5075 28
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July 2025
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    1 2 3 4 $5075 5
6 7 8 9 10 11 $5075 12
13 14 15 16 17 18 $5075 19
20 21 22 23 24 25 $5075 26
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August 2025
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          1 $5075 2
3 4 5 6 7 8 $5075 9
10 11 12 13 14 15 $5075 16
17 18 19 20 21 22 $5075 23
24 25 26 27 28 29 $5075 30
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BR1 King en suite, 2nd floorBR2 Twin bed, 2nd floorBR3 Bunk bed, 2nd floorBR4 Queen, 1st floorBR5 (2)Twin beds, 1st floorBR6 Queen, 1st floorBR7 (2) Twin beds, 1st floor
Chappaquiddick
$18,000.00 - $24,500.00 / per week
Beds 7 beds
Baths 6 Full Bath
Sleeps 13 sleeps
Edgartown Chappaquiddick 310
A captivating marriage of structure and surrounding yields an absolute masterpiece of eco-conscious modern architecture with some of the most beautifu... Read More
June 2025
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1 2 3 4 5 6 $20000 7
8 9 10 11 12 13 $24500 14
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24 25 26 27 28 29 $24500 30
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