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

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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 modern kitchen with a large island, a dining area with a table and chairs, and a view of a green garden through large windows.

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$2,244
HK$4,154 total
includes taxes & fees
11 Nov - 12 Nov
Vineyard Luxury "Yurt"
A patio with wicker chairs and a small table, a grassy yard, a wooden fence, and a view of a body of water.

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$3,425 total
includes taxes & fees
1 Nov - 2 Nov
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
A modern kitchen with stainless steel appliances, a dining area with a wooden table set for six, and a living area with a sofa and TV.

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$5,539 total
includes taxes & fees
12 Nov - 13 Nov
Oak Bluffs 4BR • 5 Min Drive to Downtown
A circular stone patio with Adirondack chairs and a small table in a forested area.

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$5,074 total
includes taxes & fees
2 Nov - 3 Nov
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A single-story house with a brick chimney, white trim, and a small porch.

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 HK$2,565
HK$5,275 total
includes taxes & fees
10 Nov - 11 Nov
Nantucket - edge of town
A two-story house with a balcony, a front porch with columns, and a sign that reads 'LIVE SWIM'.

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
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 HK$1,412
HK$4,103 total
includes taxes & fees
1 Nov - 2 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
A modern kitchen with white cabinetry, a dining area with a wooden table and white chairs, and a large window providing natural light.

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 HK$4,692
HK$13,759 total
includes taxes & fees
15 Nov - 16 Nov
New 4 BR house near center and beaches with bikes
A backyard with a patio, outdoor seating, a barbecue grill, and a wooden fence.

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 HK$1,412
HK$4,741 total
includes taxes & fees
15 Nov - 16 Nov
Charming 3-bedroom house in lovely Barnstable
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

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 HK$3,123
HK$10,727 total
includes taxes & fees
31 Oct - 1 Nov
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.

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 HK$2,975
HK$7,247 total
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.

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 HK$2,153
HK$5,356 total
includes taxes & fees
2 Nov - 3 Nov
Stunning 4-bedroom Private Fresh Water Beach Front
A spacious living area with wooden beams, a dining table, and a sofa.

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 HK$5,295
HK$8,763 total
includes taxes & fees
1 Nov - 2 Nov
The Seashell Cove - Martha's Vineyard
A modern kitchen with white cabinetry, a black stove, and a stainless steel sink.

14. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is HK$2,329
HK$7,114 total
includes taxes & fees
2 Nov - 3 Nov
West Falmouth Family Retreat Near Chapoquoit Beach
A kitchen with a dining area, a ceiling fan, and a view to an outdoor patio.

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 HK$1,569
HK$3,080 total
includes taxes & fees
31 Oct - 1 Nov
Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach
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 HK$3,516
HK$9,019 total
includes taxes & fees
31 Oct - 1 Nov
Delightful 3-bedroom house with AC in Oak Bluffs
A spacious living area with a high ceiling, a dining table, and a kitchen area.

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 HK$3,883
HK$8,456 total
includes taxes & fees
12 Nov - 13 Nov
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A living room with a sectional sofa, a coffee table, a TV, and a fireplace.

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 HK$2,008
HK$7,653 total
includes taxes & fees
31 Oct - 1 Nov
Nice home near Mashpee Commons and all Falmouth has to offer
A spacious living room with two beige sofas, a coffee table, and a patterned rug.

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 HK$1,024
HK$3,879 total
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.

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 HK$3,428
HK$7,370 total
includes taxes & fees
12 Nov - 13 Nov
< 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

Comfort Inn Hyannis - Cape Cod

Comfort Inn Hyannis - Cape Cod

8/10 Good
"Clean room, friendly professional staff, excellent location. Older hotel that appears to be recently renovated. Our room was fine, except for the tub. It was clean, but definitely needed some maintenance. If you’re looking for a fancy hotel, this one’s not for you, but it worked great for us and was well worth the price."
Jeanne 3-night trip
Posted 3 hours ago
Comfort Inn Hyannis - Cape Cod

Find out more about Chappaquiddick Island

Chappaquiddick Island Vacation Homes information

Number of reviews
309
Accommodation
948 Vacation Homes
Lowest Price
HK$3,425
Highest Price
HK$13,759

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