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. 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, (11 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is £1,035
includes taxes & fees
22 Sept - 23 Sept
New 4 BR house near center and beaches with bikes

2. Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
Oak Bluffs
8.8 out of 10, Excellent, (9 reviews)
"Loved our little cottage"
United States
Linda T.
The price is £661
includes taxes & fees
28 Sept - 29 Sept
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

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, (43 reviews)
"Great stay!"
United States
Kian S.
The price is £327
includes taxes & fees
1 Oct - 2 Oct
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

4. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is £576
includes taxes & fees
27 Sept - 28 Sept
Charming Vacation Home in Oak Bluffs.

5. Cozy Cottage walk to Menauhant Beach

Cozy Cottage walk to Menauhant Beach
East Falmouth
8.8 out of 10, Excellent, (8 reviews)
"It was a great weekend spot. Had everything we needed, nicely decorated, and in a great and private location"
United States
Grace P.
The price is £566
includes taxes & fees
30 Sept - 1 Oct
Cozy Cottage walk to Menauhant Beach

6. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.6 out of 10, (11 reviews)
"We had a perfect pre-/off-season stay with plenty of sleeping space. The location is fantastic—right between Vineyard Haven and Edgartown—making it easy to bike to both, plus there’s a beach across the street. The WiFi wasn’t working when we first arrived, but the owner was incredibly responsive and went above and beyond to fix it quickly. We’ll definitely be back!"
United States
Bethann N.
The price is £526
includes taxes & fees
29 Sept - 30 Sept
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

7. 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, (9 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is £968
includes taxes & fees
1 Oct - 2 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

8. 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 £914
includes taxes & fees
18 Oct - 19 Oct
The Seashell Cove - Martha's Vineyard

9. Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow

Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow
Falmouth
The price is £761
includes taxes & fees
28 Sept - 29 Sept
Charming 3 bedroom home just 1 MILE to Surf drive Beach! Located between downtow

10. < 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 £694
includes taxes & fees
21 Sept - 22 Sept
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

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, (42 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 £510
includes taxes & fees
21 Sept - 22 Sept
Stunning 4-bedroom Private Fresh Water Beach Front

12. 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
8.8 out of 10, Excellent, (10 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 £388
includes taxes & fees
28 Sept - 29 Sept
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

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

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (9 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
The price is £812
includes taxes & fees
4 Oct - 5 Oct
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

14. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is £600
includes taxes & fees
4 Oct - 5 Oct
West Falmouth Family Retreat Near Chapoquoit Beach

15. 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, (223 reviews)
"Great location "
United States
Stephanie B.
The price is £436
includes taxes & fees
19 Oct - 20 Oct
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

16. 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 £703
includes taxes & fees
1 Oct - 2 Oct
Nice home near Mashpee Commons and all Falmouth has to offer

17. Haven in Hatchville - newly renovated home

Haven in Hatchville - newly renovated home
East Falmouth
The price is £731
includes taxes & fees
30 Sept - 1 Oct
Haven in Hatchville - newly renovated home

18. Adorable beach house! 3 min walk to beach!

Adorable beach house! 3 min walk to beach!
Popponesset
10.0 out of 10, Exceptional, (31 reviews)
"We had a great stay! The place was clean, well decorated, and close to the beach! The property managers were also very nice and easy to reach out to!"
United States
Allison W.
The price is £806
includes taxes & fees
21 Sept - 22 Sept
Adorable beach house! 3 min walk to beach!

19. 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, (53 reviews)
"A wonderful home in a fabulous setting. The home has spacious & well laid out with a variety of beautiful outdoor spaces. Comfortable, with sufficient spaces inside and out; everyone had space to enjoy the property. We stayed for a week and never tired of the outdoor views. Convenient to great shopping and excellent beaches."
United States
Eric S.
The price is £848
includes taxes & fees
2 Oct - 3 Oct
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

20. Recently renovated 3 bedroom

Recently renovated 3 bedroom
Falmouth
10.0 out of 10, Exceptional, (3 reviews)
"Stay was awesome! Perfect house for family gatherings "
United States
Diana P.
The price is £804
includes taxes & fees
1 Oct - 2 Oct
Recently renovated 3 bedroom
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 Holiday Homes information

Number of reviews
456
Accommodation
961 Holiday Homes
Lowest Price
£388
Highest Price
£1,035

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