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

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Our top choices for Chappaquiddick Island vacation homes

1. Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
Seconsett Island
10.0 out of 10, Exceptional, (45 reviews)
"Great place with kayaks and paddle boards, beach, close to Mashpee Commons. Host was great and place was clean and quaint."
United States
Michele M.
The price is ¥24,888
¥68,453 total
includes taxes & fees
Oct 19 - Oct 20
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

2. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"This place was just what we needed! Would definitely stay again. Cozy and feels very homey! Thanks!"
United States
Chris S.
The price is ¥47,248
¥117,731 total
includes taxes & fees
Nov 11 - Nov 12
Oak Bluffs 4BR • 5 Min Drive to Downtown

3. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
7.0 out of 10, Good, (12 reviews)
"Loved this spot. Perfect central island location. Fantastic owner with an incredible response time. Would recommend this property to all5 stars"
United States
Eli R.
The price is ¥49,934
¥112,965 total
includes taxes & fees
Oct 20 - Oct 21
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

4. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (10 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is ¥62,892
¥216,047 total
includes taxes & fees
Oct 19 - Oct 20
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

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

New 4 BR house near center and beaches with bikes
Katama
9.8 out of 10, Exceptional, (13 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is ¥83,751
¥263,350 total
includes taxes & fees
Oct 19 - Oct 20
New 4 BR house near center and beaches with bikes

6. Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (224 reviews)
"Great location "
United States
Stephanie B.
The price is ¥28,444
¥82,289 total
includes taxes & fees
Nov 1 - Nov 2
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

7. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is ¥37,438
¥116,364 total
includes taxes & fees
Oct 19 - Oct 20
West Falmouth Family Retreat Near Chapoquoit Beach

8. Delightful 3-bedroom house with AC in Oak Bluffs

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
The price is ¥70,825
¥180,957 total
includes taxes & fees
Oct 30 - Oct 31
Delightful 3-bedroom house with AC in Oak Bluffs

9. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (10 reviews)
"A clean accommodating space with an accommodating host - I recommended!"
United States
Collins E.
The price is ¥78,220
¥170,331 total
includes taxes & fees
Oct 19 - Oct 20
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

10. Charming 3-bedroom house in lovely Barnstable

Charming 3-bedroom house in lovely Barnstable
Barnstable
9.6 out of 10, Exceptional, (5 reviews)
"Excellent stay! Loved the home! "
United States
Cailee B.
The price is ¥34,764
¥95,853 total
includes taxes & fees
Nov 15 - Nov 16
Charming 3-bedroom house in lovely Barnstable

11. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (31 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is ¥113,774
¥185,510 total
includes taxes & fees
Oct 19 - Oct 20
The Seashell Cove - Martha's Vineyard

12. < 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
Oak Bluffs
7.4 out of 10, Good, (3 reviews)
"House was neat architectural wise and family history of home ownership was very cool. However, listing noted there was a washer/dryer and there was not. House also noted that there was a fire pit and it was rusted through. Screen door handles were broken, windows need repair, and house has animals living in the downstairs bathroom wall. House needs updates to charge what was being charged a night. In addition, there was a Nor’easter that hit the island and we attempted to contact the host to let...
United States
Kate K.
The price is ¥69,055
¥148,444 total
includes taxes & fees
Oct 19 - Oct 20
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

13. Stunning 4-bedroom Private Fresh Water Beach Front

Stunning 4-bedroom Private Fresh Water Beach Front
East Falmouth
10.0 out of 10, Exceptional, (45 reviews)
"Great trip and time on the lake. Highly recommend this property for families looking for ease and convenience."
United States
Kathryn C.
The price is ¥44,799
¥110,230 total
includes taxes & fees
Oct 19 - Oct 20
Stunning 4-bedroom Private Fresh Water Beach Front

14. Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Barnstable
9.0 out of 10, Wonderful, (11 reviews)
"Nice location, quiet neighborhood, comfortable, and clean with a feeling of newness. Nice time of year to enjoy the porch and there was plenty of room for our group of seven. Three couches in the basement! Easy to get to town or beaches, etc. Host was helpful and communicative."
United States
Jen M.
The price is ¥21,190
¥78,754 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

15. Nantucket - edge of town

Nantucket - edge of town
West of Town
9.6 out of 10, Exceptional, (99 reviews)
"Such a great experience! Loved the property"
United States
Alex B.
The price is ¥51,673
¥106,259 total
includes taxes & fees
Oct 19 - Oct 20
Nantucket - edge of town

16. 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, (54 reviews)
"We had the best week at 67 Tide Run! The property is gorgeous. We enjoyed kayaking and fishing from the dock. It was plenty big enough for our family of 10. We are going to miss the views. It’s perfect! You cannot go wrong booking Jamie’s home."
United States
cindy w.
The price is ¥70,477
¥163,854 total
includes taxes & fees
Oct 30 - Oct 31
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

17. Entire Hyannis Home - Near Downtown & Beaches

Entire Hyannis Home - Near Downtown & Beaches
Barnstable
8.8 out of 10, Excellent, (3 reviews)
"We had a fantastic stay! The property was extremely clean from top to bottom, which immediately made us feel comfortable settling in. The beds and linens were incredibly comfortable and we all slept great.The location was also a huge plus. It is close to great restaurants, local events and plenty to do in the area, making it easy to get around and enjoy everything nearby.The host was extremely communicative and responsive, which made the whole experience smooth and stress free from booking...
United States
Bethany P.
The price is ¥25,283
¥73,427 total
includes taxes & fees
Nov 16 - Nov 17
Entire Hyannis Home - Near Downtown & Beaches

18. Pool Escape in East Falmouth

Pool Escape in East Falmouth
East Falmouth
8.0 out of 10, Very good, (2 reviews)
"Great location! Close to everything and wonderful neighborhood. The fenced in back yard with the pool is amazing. Hosts are great to work with. Very responsive to any questions or needs."
United States
Gloria C.
The price is ¥75,229
¥208,471 total
includes taxes & fees
Oct 20 - Oct 21
Pool Escape in East Falmouth

19. 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 ¥213,327
¥352,840 total
includes taxes & fees
Oct 19 - Oct 20
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

20. Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
Barnstable
10.0 out of 10, Exceptional, (7 reviews)
"Very nice property in a quiet and convenient location. Private backyard with outdoor shower. Interior was completely updated with very nice furnishings and appliances. All in all a great home that we will definitely return to. "
United States
Jim C.
The price is ¥41,717
¥105,800 total
includes taxes & fees
Oct 19 - Oct 20
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
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

Find out more about Chappaquiddick Island

Chappaquiddick Island Vacation Homes information

Number of reviews
528
Accommodation
947 Vacation Homes
Lowest Price
¥68,453
Highest Price
¥352,840

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