An aerial view of a coastal area with a lighthouse, a sandy beach, and a marina.

Chappaquiddick Island Vacation Rentals

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Our top choices for Chappaquiddick Island vacation rentals

1. Chappy cottage with private beach

Chappy cottage with private beach
Edgartown
10.0 out of 10, Exceptional, (18 reviews)
"What a gorgeous location, my family and I had a wonderful time on Chappy, will definitely be back!"
United States
Clinton G.
The price is ¥72,041
¥162,906 total
includes taxes & fees
Sep 6 - Sep 7
Chappy cottage with private beach

2. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (367 reviews)
"Overall, very good. Pool and beach area were not the most convenient to access. Short drive required."
United States
Grayson
The price is ¥32,367
¥37,044 total
includes taxes & fees
Sep 7 - Sep 8
The Club at New Seabury

3. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (29 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is ¥120,068
¥193,127 total
includes taxes & fees
Sep 6 - Sep 7
The Seashell Cove - Martha's Vineyard

4. Walk to Town/Golf Club - Renovated Edgartown Home

Walk to Town/Golf Club - Renovated Edgartown Home
Edgartown
10.0 out of 10, Exceptional, (47 reviews)
"Great house in a great location—just a short, easy walk to downtown Edgartown"
United States
Steven M.
The price is ¥84,287
¥168,896 total
includes taxes & fees
Sep 2 - Sep 3
Walk to Town/Golf Club - Renovated Edgartown Home

5. Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
10.0 out of 10, Exceptional, (3 reviews)
The price is ¥400,225
¥602,089 total
includes taxes & fees
Sep 13 - Sep 14
Beautiful Estate with salt water pool & pond with kayaks

6. Lovely two bedroom apartment with indoor fireplace

Lovely two bedroom apartment with indoor fireplace
Oak Bluffs
10.0 out of 10, Exceptional, (8 reviews)
"Great stay, flexible and responsive host. Difficult location, however, as it was not centrally located or easy to access transportation, etc."
United States
Aviva M.
The price is ¥31,539
¥119,990 total
includes taxes & fees
Sep 7 - Sep 8
Lovely two bedroom apartment with indoor fireplace

7. New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (87 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
The price is ¥15,690
¥54,054 total
includes taxes & fees
Sep 2 - Sep 3
New Seabury Cape Condo + Pool & Beach Escape

8. Make Lasting Memories In This Adorable Vineyard Cottage!

Make Lasting Memories In This Adorable Vineyard Cottage!
Oak Bluffs
9.8 out of 10, Exceptional, (155 reviews)
"Cute, compact, and had everything we needed for ourstay. I'd definitely stay there again."
United States
Karen C.
The price is ¥40,023
¥81,722 total
includes taxes & fees
Sep 2 - Sep 3
Make Lasting Memories In This Adorable Vineyard Cottage!

9. Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Tisbury
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful view of the lagoon; ideal place for a couple or single. Leisurely walk to town and close to public transportation."
United States
Adrienne W.
The price is ¥47,547
¥85,119 total
includes taxes & fees
Sep 6 - Sep 7
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

10. Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (6 reviews)
"This is a new, beautiful and tastefully decorated 2 bedroom one bathroom house with a really nice big yard. Owner was very responsive and We had everything we needed for an enjoyable stay!"
United States
Elizabeth O.
The price is ¥65,637
¥163,084 total
includes taxes & fees
Sep 7 - Sep 8
Brand New Guest house

11. Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Oak Bluffs
9.4 out of 10, Exceptional, (94 reviews)
The price is ¥48,027
¥85,834 total
includes taxes & fees
Sep 10 - Sep 11
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

12. New 4 BR house near center and beaches with bikes

New 4 BR house near center and beaches with bikes
Katama
9.6 out of 10, Exceptional, (9 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is ¥84,848
¥231,217 total
includes taxes & fees
Sep 7 - Sep 8
New 4 BR house near center and beaches with bikes

13. MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.8 out of 10, Exceptional, (12 reviews)
"This was an excellent stay at a beautiful property in Oak Bluffs! Rebecca was a great host who provided clear instructions and helped answer questions in a timely manner. Rooms were spacious, most tastefully decorated and we had everything that we needed. I definitely recommend staying here to have an unparalleled experience of the Vineyard."
United States
Priyanka D.
The price is ¥216,122
¥349,237 total
includes taxes & fees
Sep 8 - Sep 9
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

14. New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
Little Neck Bay
9.8 out of 10, Exceptional, (52 reviews)
"A wonderful home in a fabulous setting. The home has spacious & well laid out with a variety of beautiful outdoor spaces. Comfortable, with sufficient spaces inside and out; everyone had space to enjoy the property. We stayed for a week and never tired of the outdoor views. Convenient to great shopping and excellent beaches."
United States
Eric S.
The price is ¥104,059
¥206,677 total
includes taxes & fees
Sep 25 - Sep 26
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

15. Sal's Place

Sal's Place
2.0 star property
Hyannis
The price is ¥88,370
¥120,350 total
includes taxes & fees
Aug 31 - Sep 1
Sal's Place

16. Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!

Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!
Oak Bluffs
9.8 out of 10, Exceptional, (59 reviews)
"We had the best girls weekend here! The space was perfect size for us. Great spaces for sitting and chatting, both inside and on the balcony. The location was perfect, right across from the ocean waves and shells on the beach. Walking distance to town and easy access to biking. It had everything we needed."
United States
Rachael C.
The price is ¥79,389
¥147,330 total
includes taxes & fees
Sep 24 - Sep 25
Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!

17. serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
West Tisbury
The price is ¥50,428
¥125,712 total
includes taxes & fees
Sep 12 - Sep 13
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

18. WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (54 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is ¥110,302
¥171,131 total
includes taxes & fees
Sep 8 - Sep 9
WATERFRONT Downtown Cottage w/ Beach

19. Adorable beach house! 3 min walk to beach!

Adorable beach house! 3 min walk to beach!
Popponesset
9.8 out of 10, Exceptional, (30 reviews)
"We had a great stay! The place was clean, well decorated, and close to the beach! The property managers were also very nice and easy to reach out to!"
United States
Allison W.
The price is ¥104,059
¥185,972 total
includes taxes & fees
Sep 20 - Sep 21
Adorable beach house! 3 min walk to beach!

20. Quaint Beach House with AC, Pool, Hot tub area, Fire Pit, and Ocean Views

Quaint Beach House with AC, Pool, Hot tub area, Fire Pit, and Ocean Views
New Seabury
9.4 out of 10, Exceptional, (3 reviews)
"Great neighborhood with a home that allows for privacy and togetherness! Host was responsive and welcoming. Thank you!"
United States
Christopher C.
The price is ¥200,113
¥420,499 total
includes taxes & fees
Sep 19 - Sep 20
Quaint Beach House with AC, Pool, Hot tub area, Fire Pit, and Ocean Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chappaquiddick Island Hotel Reviews

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