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. Vineyard Luxury "Yurt"

Vineyard Luxury "Yurt"
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"The yurt was clean and nice and served all of our needs."
United States
David C.
The price is ¥43,229
¥81,242 total
includes taxes & fees
Nov 11 - Nov 12
Vineyard Luxury "Yurt"

2. 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 ¥24,849
¥68,345 total
includes taxes & fees
Nov 5 - Nov 6
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

3. 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 ¥42,456
¥111,395 total
includes taxes & fees
Nov 11 - Nov 12
Oak Bluffs 4BR • 5 Min Drive to Downtown

4. 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 ¥41,494
¥102,037 total
includes taxes & fees
Nov 5 - Nov 6
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

5. Nantucket - edge of town

Nantucket - edge of town
West of Town
9.6 out of 10, Exceptional, (100 reviews)
"Such a great experience! Loved the property"
United States
Alex B.
The price is ¥51,591
¥106,091 total
includes taxes & fees
Nov 1 - Nov 2
Nantucket - edge of town

6. Love Sand, Madaket on the Beach, Lovely Seaside Home

Love Sand, Madaket on the Beach, Lovely Seaside Home
Nantucket
9.8 out of 10, Exceptional, (58 reviews)
"Almost 270 degree views of the ocean — spectacular setting with lots of privacy, great amenities and miles of beach to explore. Very accessible to town. We loved our stay!"
United States
Marjorie A.
Love Sand, Madaket on the Beach, Lovely Seaside Home

7. 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, (225 reviews)
"Great location "
United States
Stephanie B.
The price is ¥28,399
¥82,520 total
includes taxes & fees
Nov 4 - Nov 5
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

8. 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 ¥94,346
¥276,679 total
includes taxes & fees
Nov 15 - Nov 16
New 4 BR house near center and beaches with bikes

9. 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 ¥28,399
¥95,341 total
includes taxes & fees
Nov 15 - Nov 16
Charming 3-bedroom house in lovely Barnstable

10. 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 ¥62,792
¥215,704 total
includes taxes & fees
Oct 30 - Oct 31
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

11. Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops
Falmouth
10.0 out of 10, Exceptional, (19 reviews)
"Jessica was absolutely amazing and so was the house! We stayed here for our family vacation and it was perfect. 5 stars all around!"
United States
Kelsey B.
The price is ¥59,822
¥146,654 total
includes taxes & fees
Nov 5 - Nov 6
Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

12. 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 ¥43,308
¥107,708 total
includes taxes & fees
Nov 4 - Nov 5
Stunning 4-bedroom Private Fresh Water Beach Front

13. 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 ¥106,495
¥176,231 total
includes taxes & fees
Nov 1 - Nov 2
The Seashell Cove - Martha's Vineyard

14. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is ¥42,917
¥137,319 total
includes taxes & fees
Oct 30 - Oct 31
West Falmouth Family Retreat Near Chapoquoit Beach

15. Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach

Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach
Sandwich
The price is ¥31,554
¥61,934 total
includes taxes & fees
Oct 30 - Oct 31
Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach

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

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
The price is ¥70,713
¥181,376 total
includes taxes & fees
Oct 31 - Nov 1
Delightful 3-bedroom house with AC in Oak Bluffs

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

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.8 out of 10, Exceptional, (11 reviews)
"A clean accommodating space with an accommodating host - I recommended!"
United States
Collins E.
The price is ¥78,096
¥170,062 total
includes taxes & fees
Oct 30 - Oct 31
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

18. Nice home near Mashpee Commons and all Falmouth has to offer

Nice home near Mashpee Commons and all Falmouth has to offer
Falmouth
6.0 out of 10, (3 reviews)
"Quiet location"
United States
andrea m.
The price is ¥40,381
¥153,915 total
includes taxes & fees
Nov 4 - Nov 5
Nice home near Mashpee Commons and all Falmouth has to offer

19. 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 ¥22,877
¥80,886 total
includes taxes & fees
Nov 4 - Nov 5
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

20. < 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 ¥68,945
¥148,209 total
includes taxes & fees
Oct 31 - Nov 1
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
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
309
Accommodation
947 Vacation Homes
Lowest Price
¥68,345
Highest Price
¥276,679

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