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

Chappaquiddick Island Vacation Rentals

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Our top choices for Chappaquiddick Island vacation homes

1. 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 CA $380
CA $900 total
includes taxes & fees
Nov 26 - Nov 27
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

2. 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 CA $352
CA $680 total
includes taxes & fees
Nov 12 - Nov 13
Vineyard Luxury "Yurt"

3. 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 CA $223
CA $590 total
includes taxes & fees
Nov 12 - Nov 13
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

4. 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 CA $380
CA $999 total
includes taxes & fees
Nov 20 - Nov 21
Oak Bluffs 4BR • 5 Min Drive to Downtown

5. 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 CA $465
CA $1,165 total
includes taxes & fees
Dec 6 - Dec 7
Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

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 CA $335
CA $1,269 total
includes taxes & fees
Nov 16 - Nov 17
Love Sand, Madaket on the Beach, Lovely Seaside Home

7. 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)
"Excellent house close to everything. Great neighborhood. We enjoyed our stay in this very comfortable house. We certainly would rent again."
United States
Jim A.
The price is CA $848
CA $2,361 total
includes taxes & fees
Nov 15 - Nov 16
New 4 BR house near center and beaches with bikes

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, (203 reviews)
"Great stay again"
United States
Ray S.
The price is CA $319
CA $770 total
includes taxes & fees
Nov 14 - Nov 15
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

9. 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 CA $254
CA $738 total
includes taxes & fees
Nov 17 - Nov 18
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

10. Welcome to your Cape Cod getaway! ONLY 1.5 miles to Menauhant Beach, this charmi

Welcome to your Cape Cod getaway! ONLY 1.5 miles to Menauhant Beach, this charmi
East Falmouth
The price is CA $460
CA $1,238 total
includes taxes & fees
Nov 17 - Nov 18
Welcome to your Cape Cod getaway! ONLY 1.5 miles to Menauhant Beach, this charmi

11. 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 CA $491
CA $1,376 total
includes taxes & fees
Nov 19 - Nov 20
Coastal chic meets French Provençal in this newly renovated oceanfront home.

12. Spacious 5BR Falmouth Family Retreat with Deck, Ping Pong Table & Central A/C

Spacious 5BR Falmouth Family Retreat with Deck, Ping Pong Table & Central A/C
Falmouth
The price is CA $360
CA $1,480 total
includes taxes & fees
Nov 12 - Nov 13
Spacious 5BR Falmouth Family Retreat with Deck, Ping Pong Table & Central A/C

13. Nantucket - on the outskirts of the city

Nantucket - on the outskirts of the city
West of Town
9.6 out of 10, Exceptional, (101 reviews)
"Such a great experience! Loved the property"
United States
Alex B.
The price is CA $464
CA $954 total
includes taxes & fees
Nov 22 - Nov 23
Nantucket - on the outskirts of the city

14. 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 CA $958
CA $1,436 total
includes taxes & fees
Nov 15 - Nov 16
The Seashell Cove - Martha's Vineyard

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 CA $356
CA $1,252 total
includes taxes & fees
Nov 12 - Nov 13
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 CA $172
CA $694 total
includes taxes & fees
Nov 12 - Nov 13
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

17. < 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 CA $620
CA $1,297 total
includes taxes & fees
Nov 12 - Nov 13
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

18. 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 CA $284
CA $529 total
includes taxes & fees
Nov 12 - Nov 13
Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach

19. Sal's Place

Sal's Place
2.0 star property
Hyannis
The price is CA $353
CA $573 total
includes taxes & fees
Nov 17 - Nov 18
Sal's Place

20. 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 CA $2,837
CA $4,202 total
includes taxes & fees
Nov 30 - Dec 1
Beautiful Estate with salt water pool & pond with kayaks
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

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Chappaquiddick Island Vacation Homes information

Number of reviews
672
Accommodation
942 Vacation Homes
Lowest Price
CA $573
Highest Price
CA $4,202

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