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 holiday 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 HK$1,969
HK$3,715 total
includes taxes & fees
11 Nov - 12 Nov
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 HK$1,236
HK$3,344 total
includes taxes & fees
3 Nov - 4 Nov
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 HK$2,111
HK$5,320 total
includes taxes & fees
11 Nov - 12 Nov
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 HK$2,063
HK$4,828 total
includes taxes & fees
3 Nov - 4 Nov
1 Mi to Ferry Terminal: Oak Bluffs Family 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 HK$4,691
HK$12,469 total
includes taxes & fees
16 Nov - 17 Nov
New 4 BR house near center and beaches with bikes

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.
The price is HK$1,851
HK$7,017 total
includes taxes & fees
16 Nov - 17 Nov
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, (227 reviews)
"Great location "
United States
Stephanie B.
The price is HK$1,412
HK$4,103 total
includes taxes & fees
5 Nov - 6 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

8. LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Nantucket Town
10.0 out of 10, Exceptional, (202 reviews)
"Great stay again"
United States
Ray S.
The price is HK$1,765
HK$4,259 total
includes taxes & fees
14 Nov - 15 Nov
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

9. 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 HK$2,581
HK$6,455 total
includes taxes & fees
1 Dec - 2 Dec
Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

10. 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 HK$5,648
HK$8,754 total
includes taxes & fees
4 Nov - 5 Nov
The Seashell Cove - Martha's Vineyard

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 HK$2,153
HK$5,356 total
includes taxes & fees
3 Nov - 4 Nov
Stunning 4-bedroom Private Fresh Water Beach Front

12. 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 HK$2,565
HK$5,275 total
includes taxes & fees
8 Nov - 9 Nov
Nantucket - edge of town

13. < 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 HK$3,428
HK$7,001 total
includes taxes & fees
3 Nov - 4 Nov
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

14. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is HK$2,329
HK$6,764 total
includes taxes & fees
3 Nov - 4 Nov
West Falmouth Family Retreat Near Chapoquoit Beach

15. 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 HK$1,984
HK$7,256 total
includes taxes & fees
3 Nov - 4 Nov
Nice home near Mashpee Commons and all Falmouth has to offer

16. 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 HK$1,024
HK$3,879 total
includes taxes & fees
3 Nov - 4 Nov
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

17. Coastal chic meets French Provençal in this newly renovated oceanfront home.

Coastal chic meets French Provençal in this newly renovated oceanfront home.
East Falmouth
10.0 out of 10, Exceptional, (101 reviews)
"Great views, beautiful setting . Scott was so attentive and easy to work with. We had a great time!"
United States
Ben L.
The price is HK$3,522
HK$8,619 total
includes taxes & fees
19 Nov - 20 Nov
Coastal chic meets French Provençal in this newly renovated oceanfront home.

18. 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)
"Brenda and Derek were amazing hosts. They have a beautifully landscaped property with all the amenities needed for a relaxing family vacation. They are super responsive and take a lot of pride in giving their guests a top-notch experience. We will definitely consider staying at their properties again."
United States
Lamar A.
The price is HK$15,690
HK$23,773 total
includes taxes & fees
30 Nov - 1 Dec
Beautiful Estate with salt water pool & pond with kayaks

19. 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 HK$1,569
HK$2,927 total
includes taxes & fees
3 Nov - 4 Nov
Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach

20. 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 HK$4,315
HK$9,185 total
includes taxes & fees
6 Nov - 7 Nov
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
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
816
Accommodation
940 Vacation Homes
Lowest Price
HK$3,344
Highest Price
HK$23,773

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