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

Holiday Homes in Chappaquiddick Island

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Chappaquiddick Island holiday homes

A boat docked at a concrete pier with a sandy shore in the background.

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 NZ$756
includes taxes & fees
1 Nov - 2 Nov
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

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 NZ$1,235
includes taxes & fees
11 Nov - 12 Nov
Oak Bluffs 4BR • 5 Min Drive to Downtown
A circular stone patio with Adirondack chairs and a small table in a forested area.

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 NZ$1,089
includes taxes & fees
29 Oct - 30 Oct
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A two-story house with a balcony, a front porch with columns, and a sign that reads 'LIVE SWIM'.

4. 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.
The price is NZ$1,545
includes taxes & fees
16 Nov - 17 Nov
Love Sand, Madaket on the Beach, Lovely Seaside Home
A modern kitchen with white cabinetry, a dining area with a wooden table and white chairs, and a large window providing natural light.

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 NZ$2,873
includes taxes & fees
15 Nov - 16 Nov
New 4 BR house near center and beaches with bikes
A modern kitchen with a large island, a dining area with a table and chairs, and a view of a green garden through large windows.

6. 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 NZ$901
includes taxes & fees
30 Oct - 31 Oct
Vineyard Luxury "Yurt"
A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

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 NZ$904
includes taxes & fees
2 Nov - 3 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
A living room with a sectional sofa, a coffee table, a TV, and a fireplace.

8. 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.
Nice home near Mashpee Commons and all Falmouth has to offer
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

9. 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 NZ$2,304
includes taxes & fees
29 Oct - 30 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A spacious kitchen with a large island, wooden flooring, and a dining area with chairs and a table.

10. 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 NZ$1,600
includes taxes & fees
1 Nov - 2 Nov
Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops
A wooden deck overlooking a calm lake with trees and houses in the background.

11. 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 NZ$1,155
includes taxes & fees
1 Nov - 2 Nov
Stunning 4-bedroom Private Fresh Water Beach Front
A modern kitchen with white cabinetry, a black stove, and a stainless steel sink.

12. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is NZ$1,338
includes taxes & fees
6 Nov - 7 Nov
West Falmouth Family Retreat Near Chapoquoit Beach
A sandy beach with a calm lake and a forested hill in the background.

13. 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 NZ$1,048
includes taxes & fees
15 Nov - 16 Nov
Charming 3-bedroom house in lovely Barnstable
A spacious living area with a high ceiling, a dining table, and a kitchen area.

14. 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 NZ$1,834
includes taxes & fees
10 Nov - 11 Nov
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A single-story house with a brick chimney, white trim, and a small porch.

15. 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 NZ$1,132
includes taxes & fees
1 Nov - 2 Nov
Nantucket - edge of town
A modern kitchen with a central island, bar stools, stainless steel appliances, and a large window with a view of the outdoors.

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

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
The price is NZ$1,983
includes taxes & fees
30 Oct - 31 Oct
Delightful 3-bedroom house with AC in Oak Bluffs
A wide sandy beach with footprints leading to the water, a clear sky, and distant buildings.

17. 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 NZ$897
includes taxes & fees
2 Nov - 3 Nov
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
A spacious living room with a wooden staircase, a fireplace, and a leather sofa.

18. < 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 NZ$1,608
includes taxes & fees
10 Nov - 11 Nov
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
A spacious living area with wooden beams, a dining table, and a sofa.

19. 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 NZ$1,900
includes taxes & fees
1 Nov - 2 Nov
The Seashell Cove - Martha's Vineyard
Private kitchen

20. Entire Hyannis Home - Near Downtown & Beaches

Entire Hyannis Home - Near Downtown & Beaches
Barnstable
8.6 out of 10, Excellent, (4 reviews)
"We had a lovely stay! The location was great, with plenty of bars and restaurants nearby. The place was clean, spacious and had everything we needed. Rebecca made the whole process really easy from start to finish. Thank you for a lovely stay!"
United Kingdom
Ellie M.
The price is NZ$850
includes taxes & fees
18 Nov - 19 Nov
Entire Hyannis Home - Near Downtown & Beaches
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

Inn on the Square

Inn on the Square

8/10 Good
"Close to town, restaurants, shopping and cafes"
patricia 1-night trip
Posted 10 hours ago
Inn on the Square

Find out more about Chappaquiddick Island

Chappaquiddick Island Holiday Homes information

Number of reviews
313
Accommodation
948 Holiday Homes
Lowest Price
NZ$756
Highest Price
NZ$2,873

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