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

Holiday Homes in Chappaquiddick Island

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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 NZ$2,401
includes taxes & fees
16 Sept - 17 Sept
New 4 BR house near center and beaches with bikes

2. 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 NZ$1,298
includes taxes & fees
13 Sept - 14 Sept
Cozy Cottage walk to Menauhant Beach

3. 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 NZ$1,431
includes taxes & fees
17 Sept - 18 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

4. 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 NZ$785
includes taxes & fees
1 Oct - 2 Oct
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

5. 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 NZ$1,204
includes taxes & fees
13 Sept - 14 Sept
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

6. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is NZ$1,366
includes taxes & fees
27 Sept - 28 Sept
Charming Vacation Home in Oak Bluffs.

7. < 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 NZ$1,568
includes taxes & fees
14 Sept - 15 Sept
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

8. 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 NZ$2,246
includes taxes & fees
1 Oct - 2 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

9. 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 NZ$1,239
includes taxes & fees
21 Sept - 22 Sept
Stunning 4-bedroom Private Fresh Water Beach Front

10. 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 NZ$850
includes taxes & fees
15 Sept - 16 Sept
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

11. 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, (221 reviews)
"Great location "
United States
Stephanie B.
The price is NZ$1,087
includes taxes & fees
13 Oct - 14 Oct
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

12. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
The price is NZ$1,448
includes taxes & fees
7 Oct - 8 Oct
West Falmouth Family Retreat Near Chapoquoit Beach

13. 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 NZ$1,494
includes taxes & fees
24 Sept - 25 Sept
Nice home near Mashpee Commons and all Falmouth has to offer

14. Haven in Hatchville - newly renovated home

Haven in Hatchville - newly renovated home
East Falmouth
The price is NZ$1,655
includes taxes & fees
22 Sept - 23 Sept
Haven in Hatchville - newly renovated home

15. 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 NZ$2,032
includes taxes & fees
20 Sept - 21 Sept
Recently renovated 3 bedroom

16. Nantucket - edge of town

Nantucket - edge of town
West of Town
9.6 out of 10, Exceptional, (96 reviews)
"Mary is such a great host and such a sweet person."
United States
Pathfinder Tree S.
The price is NZ$1,264
includes taxes & fees
21 Sept - 22 Sept
Nantucket - edge of town

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

Adorable beach house! 3 min walk to beach!
Popponesset
9.8 out of 10, Exceptional, (30 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 NZ$1,866
includes taxes & fees
20 Sept - 21 Sept
Adorable beach house! 3 min walk to beach!

18. Spring Escape in Hatchville – Sleeps 6 + Dogs!

Spring Escape in Hatchville – Sleeps 6 + Dogs!
Falmouth
10.0 out of 10, Exceptional, (13 reviews)
"Enjoyed our stay. Everything was clean and well kept. "
United States
Lynn S.
The price is NZ$1,382
includes taxes & fees
13 Sept - 14 Sept
Spring Escape in Hatchville – Sleeps 6 + Dogs!

19. 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 NZ$1,630
includes taxes & fees
23 Sept - 24 Sept
Welcome to your Cape Cod getaway! ONLY 1.5 miles to Menauhant Beach, this charmi

20. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is NZ$1,575
includes taxes & fees
13 Sept - 14 Sept
Walk to Beach! Oak Bluffs Home & Studio
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
469
Accommodation
948 Holiday Homes
Lowest Price
NZ$850
Highest Price
NZ$2,401

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