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
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 (3)
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
June 2025
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31    
August 2025
Su Mo Tu We Th Fr Sa
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 $3400 23
24 25 26 27 28 29 30
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out

BR1 King En Suite, Second FloorBR2 King, First FloorBR3 King, First FloorBR4 King, First FloorBR4 King or (2) Twin Beds, First FloorAdditional SleepingQueen En Suite, Lower Level A/C split units in bedrooms & living area
Chappaquiddick Pet Friendly
$12,000.00 - $17,000.00 / per week
Beds 5 beds
Baths 3 Full, 1 Half Bath
Sleeps 12 sleeps
Edgartown Chappaquiddick 421
This spacious 5 Bedroom home with a brand-new 20x60 saltwater pool and 8x12 hot tub is the ultimate Chappy getaway. Walk into the main level and you w... Read More
June 2025
Su Mo Tu We Th Fr Sa
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 $12000 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    1 2 3 4 $14000 5
6 7 8 9 10 11 $14000 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31    
August 2025
Su Mo Tu We Th Fr Sa
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out

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
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $10000 7
8 9 10 11 12 13 $13000 14
15 16 17 18 19 20 $13000 21
22 23 24 25 26 27 $13000 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    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
27 28 29 30 31    
August 2025
Su Mo Tu We Th Fr Sa
          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
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out

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
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $7000 7
8 9 10 11 12 13 $7000 14
15 16 17 18 19 20 $7000 21
22 23 24 25 26 27 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 $15000 12
13 14 15 16 17 18 $15000 19
20 21 22 23 24 25 $15000 26
27 28 29 30 31    
August 2025
Su Mo Tu We Th Fr Sa
          1 2
3 4 5 6 7 8 $15000 9
10 11 12 13 14 15 $15000 16
17 18 19 20 21 22 $15000 23
24 25 26 27 28 29 $10000 30
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out

BR1 Queen en suite with shower, AC split, 1st floorBR2 Queen, 1st floor, AC SplitBR3 King en suite with shower, AC Split, 2nd floorBR4 King, 2nd floorBR5 (2) Twin beds, AC Split, 2nd floorBR6 (2) Twin beds, AC Split, 2nd floorHall bathroom, 2nd floorHalf bath off kitchen, 1st floor
Chappaquiddick
$8,250.00 - $25,300.00 / per week
Beds 6 beds
Baths 3 Full, 1 Half Bath
Sleeps 12 sleeps
Edgartown Chappaquiddick 316
Ocean all around! This is the perfect Chappy retreat for your family vacation this summer. Stunning views from almost every room featuring new furni... Read More
June 2025
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $15400 7
8 9 10 11 12 13 $15400 14
15 16 17 18 19 20 $17600 21
22 23 24 25 26 27 $18700 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 $23100 19
20 21 22 23 24 25 $23100 26
27 28 29 30 31    
August 2025
Su Mo Tu We Th Fr Sa
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 $25300 16
17 18 19 20 21 22 $25300 23
24 25 26 27 28 29 $19800 30
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out

BR1 (2)Twin bunk beds, 2nd floorBR2 queen, 2nd floorHall bath with tub/shower, 2nd floorBR3 King en suite tub/shower, 2nd floorHalf bath, 1st floorLaundry, 1st floor
Chappaquiddick Pet Friendly
$3,150.00 - $4,200.00 / per week
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps 8 sleeps
Rating 5 (1)
Edgartown Chappaquiddick 415
This Chappy pet-friendly three bedroom colonial is located in a quiet area and close to East Beach. This home offers an open first floor plan, a sun p... Read More
June 2025
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $3850 7
8 9 10 11 12 13 $3150 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31    
August 2025
Su Mo Tu We Th Fr Sa
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 $4200 23
24 25 26 27 28 29 $3150 30
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out

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
June 2025
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31    
August 2025
Su Mo Tu We Th Fr Sa
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out

BR1 Pair of Twins, 1st floorBR2 Double, Twin, 1st floorHall bath with tub/shower, 1st floorBR3 King and Couch, 2nd floorBR4 Pair of Twins, 2nd floorUpper deck access through BR3
Chappaquiddick Pet Friendly
$2,200.00 - $4,000.00 / per week
Beds 4 beds
Baths 2 Full Bath
Sleeps 8 sleeps
Rating 5 (1)
Edgartown Chappaquiddick 301
This house sings the harmony of a well-traveled Vineyarder. Embodying all the essentials with just enough space, perfectly composed and effortlessly c... Read More
June 2025
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31    
August 2025
Su Mo Tu We Th Fr Sa
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out

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
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $3500 7
8 9 10 11 12 13 $3500 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31    
August 2025
Su Mo Tu We Th Fr Sa
          1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out

BR1 King En Suite with Tub/Shower, First FloorQueen & Twin Bed, Second Floor Loft Half Bath, Second Floor Loft
Hot HOT 11
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
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $2500 7
8 9 10 11 12 13 $3000 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 $3000 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31    
August 2025
Su Mo Tu We Th Fr Sa
          1 2
3 4 5 6 7 8 $3000 9
10 11 12 13 14 15 $3000 16
17 18 19 20 21 22 23
24 25 26 27 28 29 30
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out

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 - $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
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 $5000 7
8 9 10 11 12 13 $5000 14
15 16 17 18 19 20 $5000 21
22 23 24 25 26 27 $5000 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    1 2 3 4 $5000 5
6 7 8 9 10 11 $5000 12
13 14 15 16 17 18 $5000 19
20 21 22 23 24 25 $5000 26
27 28 29 30 31    
August 2025
Su Mo Tu We Th Fr Sa
          1 $5000 2
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
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out

BR1 Double, First FloorHall Bath with Tub Only, First FloorBR2 Twin Beds, First FloorDetached Structure: Overflow Daybed (no A/C)
Chappaquiddick
$2,450.00 - $4,850.00 / per week
Beds 2 beds
Baths 1 Full Bath
Sleeps 4 sleeps
Edgartown Chappaquiddick 319
Enjoy life's simple pleasures at this two bedroom Chappy cottage named the Rudder. Stunning views over the Vineyard Sound with a beautiful porch to lo... Read More
June 2025
Su Mo Tu We Th Fr Sa
1 2 3 4 5 6 7
8 9 10 11 12 13 14
15 16 17 18 19 20 21
22 23 24 25 26 27 28
29 30          
July 2025
Su Mo Tu We Th Fr Sa
    1 2 3 4 5
6 7 8 9 10 11 12
13 14 15 16 17 18 19
20 21 22 23 24 25 26
27 28 29 30 31    
August 2025
Su Mo Tu We Th Fr Sa
          1 $4850 2
3 4 5 6 7 8 $4850 9
10 11 12 13 14 15 16
17 18 19 20 21 22 23
24 25 26 27 28 29 $4850 30
31            
Prev
Next
Available
Unavailable
Check-In
Check-Out

Tell us what you're looking for and someone will contact you with available options.

I agree