Chappaquiddick Island Vacation Homes

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

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!

Seconsett Island

Michele M.

HK$3,344 total

includes taxes & fees

29 Oct - 30 Oct

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

Chris S.

HK$5,539 total

includes taxes & fees

11 Nov - 12 Nov

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!

Oak Bluffs

Eli R.

HK$5,073 total

includes taxes & fees

1 Nov - 2 Nov

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

Nantucket

Marjorie A.

HK$7,017 total

includes taxes & fees

16 Nov - 17 Nov

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

Katama

Susan M.

HK$13,757 total

includes taxes & fees

23 Nov - 24 Nov

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"

Oak Bluffs

David C.

HK$4,057 total

includes taxes & fees

30 Oct - 31 Oct

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

Falmouth

Stephanie B.

HK$4,103 total

includes taxes & fees

3 Nov - 4 Nov

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

Falmouth

andrea m.

HK$7,654 total

includes taxes & fees

2 Nov - 3 Nov

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

Oak Bluffs

Sherri R.

HK$10,725 total

includes taxes & fees

30 Oct - 31 Oct

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

Falmouth

Kelsey B.

HK$7,292 total

includes taxes & fees

3 Nov - 4 Nov

A wooden deck overlooking a calm lake with trees and houses in the background.

11. Stunning 4-bedroom Private Fresh Water Beach Front

East Falmouth

Kathryn C.

HK$5,355 total

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with white cabinetry, a black stove, and a stainless steel sink.

12. West Falmouth Family Retreat Near Chapoquoit Beach

Falmouth

HK$6,053 total

includes taxes & fees

2 Nov - 3 Nov

A sandy beach with a calm lake and a forested hill in the background.

13. Charming 3-bedroom house in lovely Barnstable

Barnstable

Cailee B.

HK$4,740 total

includes taxes & fees

15 Nov - 16 Nov

A spacious living area with a high ceiling, a dining table, and a kitchen area.

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

Oak Bluffs

Collins E.

HK$8,456 total

includes taxes & fees

30 Oct - 31 Oct

A single-story house with a brick chimney, white trim, and a small porch.

15. Nantucket - edge of town

West of Town

Alex B.

HK$5,275 total

includes taxes & fees

1 Nov - 2 Nov

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

Oak Bluffs

HK$9,018 total

includes taxes & fees

30 Oct - 31 Oct

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

Barnstable

Jen M.

HK$4,022 total

includes taxes & fees

2 Nov - 3 Nov

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

Oak Bluffs

"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...

Kate K.

HK$7,369 total

includes taxes & fees

30 Oct - 31 Oct

A spacious living area with wooden beams, a dining table, and a sofa.

19. The Seashell Cove - Martha's Vineyard

Katama

Eric C.

HK$9,209 total

includes taxes & fees

30 Oct - 31 Oct

20. Entire Hyannis Home - Near Downtown & Beaches

Barnstable

Ellie M.

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Top Chappaquiddick Island Hotel Reviews

Summercamp

8/10 Good

"The stay was great! The only issue was it took almost 10 minutes for the water to get hot!"

Faraway Martha's Vineyard

10/10 Excellent

"Lovely property , it seemed it was the end of the season when we visited, so it was very quiet, and maintenance had started in the hotel, not that it bothered us at all . Loved the record player and the hot tub and bikes . The pub/restaurant was very good , with very helpful barmaid (Sophia) who on top of great service in the bar helped us plan the next part of our trip in Boston ."

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