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

Chappaquiddick Island Holiday Rentals

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Our top choices for Chappaquiddick Island holiday rentals

1. Chappy cottage with private beach

Chappy cottage with private beach
Edgartown
10.0 out of 10, Exceptional, (18 reviews)
"What a gorgeous location, my family and I had a wonderful time on Chappy, will definitely be back!"
United States
Clinton G.
Chappy cottage with private beach

2. New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (85 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
The price is HK$854
HK$2,728 total
includes taxes & fees
17 Aug - 18 Aug
New Seabury Cape Condo + Pool & Beach Escape

3. Walk to Beach & Lighthouse: Oak Bluffs Studio!

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
8.6 out of 10, Excellent, (7 reviews)
"Very accommodating early check in and great communication "
United States
Katelyn K.
The price is HK$1,059
HK$2,979 total
includes taxes & fees
31 Aug - 1 Sept
Walk to Beach & Lighthouse: Oak Bluffs Studio!

4. Small One Bedroom Private Cottage on Large Quiet Property.

Small One Bedroom Private Cottage on Large Quiet Property.
Tisbury
10.0 out of 10, Exceptional, (16 reviews)
"Nice, quaint cottage. Perfect for a couple's getaway! Location was convenient for walking to shops and restaurants."
United States
Randy T.
The price is HK$2,353
HK$4,003 total
includes taxes & fees
23 Aug - 24 Aug
Small One Bedroom Private Cottage on Large Quiet Property.

5. Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (5 reviews)
"This is a new, beautiful and tastefully decorated 2 bedroom one bathroom house with a really nice big yard. Owner was very responsive and We had everything we needed for an enjoyable stay!"
United States
Elizabeth O.
Brand New Guest house

6. Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
The price is HK$1,176
HK$1,795 total
includes taxes & fees
31 Aug - 1 Sept
Charming studio in tranquil Falmouth with AC

7. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (364 reviews)
"The condo had everything we needed, and was clean, however there were a lot of ants on the main floor, mostly in the kitchen. This should definitely be looked into and maybe some traps set. There was a washer/dryer which was great and room service each day to change towels."
Canada
Rylea
The price is HK$5,927
HK$6,784 total
includes taxes & fees
5 Aug - 6 Aug
The Club at New Seabury

8. New 4 BR house near center and beaches with bikes

New 4 BR house near center and beaches with bikes
Katama
10.0 out of 10, Exceptional, (7 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is HK$8,627
HK$17,162 total
includes taxes & fees
31 Aug - 1 Sept
New 4 BR house near center and beaches with bikes

9. Loft Hideaway in Falmouth Village

Loft Hideaway in Falmouth Village
Falmouth
9.6 out of 10, Exceptional, (5 reviews)
"We really enjoyed our visit!! The location can’t be beat and Falmouth was a great place to explore. "
United States
Nancy F.
Loft Hideaway in Falmouth Village

10. Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Oak Bluffs
9.4 out of 10, Exceptional, (94 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
The price is HK$3,725
HK$5,957 total
includes taxes & fees
26 Aug - 27 Aug
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

11. Secluded-Entire 2nd floor Suite with Private Bath

Secluded-Entire 2nd floor Suite with Private Bath
Barnstable
10.0 out of 10, Exceptional, (3 reviews)
"Great host, great place!"
United States
Brandon S.
The price is HK$1,122
HK$2,057 total
includes taxes & fees
30 Aug - 31 Aug
Secluded-Entire 2nd floor Suite with Private Bath

12. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.8 out of 10, (9 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 HK$2,141
HK$5,177 total
includes taxes & fees
2 Aug - 3 Aug
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

13. Bike to Beach: Centerville Home w/ Deck!

Bike to Beach: Centerville Home w/ Deck!
Centerville
9.6 out of 10, Exceptional, (21 reviews)
"The house was very clean, updated and comfortable. It suited our needs beautifully. Communication was great and check in was very easy. The location was very convenient and it was wonderful to have ample parking."
United States
Jeanne S.
The price is HK$1,545
HK$5,018 total
includes taxes & fees
26 Aug - 27 Aug
Bike to Beach: Centerville Home w/ Deck!

14. Serene Haven w/ No Shared Spaces | Cape Cod

Serene Haven w/ No Shared Spaces | Cape Cod
Marston Mills
10.0 out of 10, Exceptional, (18 reviews)
"Marston Hills is a great location for getting to many great areas of Cape Cod. The house was very clean and nicely furnished. "
United States
Dana S.
The price is HK$1,927
HK$3,139 total
includes taxes & fees
4 Aug - 5 Aug
Serene Haven w/ No Shared Spaces | Cape Cod

15. Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Falmouth
10.0 out of 10, Exceptional, (15 reviews)
"This is a beautiful and unique home with plenty of space and activities for the family. The photos were accurate and there was so much space for everyone to relax. We enjoyed our stay so much. "
United States
Lisa F.
The price is HK$2,784
HK$6,140 total
includes taxes & fees
24 Aug - 25 Aug
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

16. 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, (6 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is HK$10,117
HK$19,044 total
includes taxes & fees
24 Aug - 25 Aug
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

17. Quintessential coastal studio with beach access, BBQ area, patio, & water views

Quintessential coastal studio with beach access, BBQ area, patio, & water views
Yarmouth
9.0 out of 10, Wonderful, (6 reviews)
"Charming little place! "
United States
Amber G.
The price is HK$1,780
HK$3,997 total
includes taxes & fees
30 Aug - 31 Aug
Quintessential coastal studio with beach access, BBQ area, patio, & water views

18. Bike to Beach: Centerville Home w/ Deck!

Bike to Beach: Centerville Home w/ Deck!
3.0 star property
Centerville
The price is HK$2,047
HK$5,088 total
includes taxes & fees
26 Aug - 27 Aug
Bike to Beach: Centerville Home w/ Deck!

19. Classic Cape Escape in Charming Cotuit

Classic Cape Escape in Charming Cotuit
Contuit
9.0 out of 10, Wonderful, (4 reviews)
"clean and spacious house!"
United States
Greg A.
Classic Cape Escape in Charming Cotuit
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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