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 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 CA $153
CA $490 total
includes taxes & fees
Aug 17 - Aug 18
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 CA $189
CA $527 total
includes taxes & fees
Aug 31 - Sep 1
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 CA $420
CA $715 total
includes taxes & fees
Aug 23 - Aug 24
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.
The price is CA $693
CA $1,582 total
includes taxes & fees
Aug 24 - Aug 25
Brand New Guest house

6. Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
The price is CA $210
CA $317 total
includes taxes & fees
Aug 31 - Sep 1
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 CA $707
CA $809 total
includes taxes & fees
Aug 23 - Aug 24
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 CA $1,541
CA $3,065 total
includes taxes & fees
Aug 31 - Sep 1
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.
The price is CA $307
CA $631 total
includes taxes & fees
Aug 9 - Aug 10
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 CA $665
CA $1,062 total
includes taxes & fees
Aug 24 - Aug 25
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 CA $223
CA $399 total
includes taxes & fees
Aug 2 - Aug 3
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 CA $382
CA $925 total
includes taxes & fees
Aug 2 - Aug 3
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 CA $276
CA $905 total
includes taxes & fees
Aug 26 - Aug 27
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 CA $344
CA $561 total
includes taxes & fees
Aug 4 - Aug 5
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, (16 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.
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 CA $701
CA $2,099 total
includes taxes & fees
Sep 1 - Sep 2
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 CA $299
CA $683 total
includes taxes & fees
Aug 30 - Aug 31
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 CA $347
CA $888 total
includes taxes & fees
Aug 26 - Aug 27
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

Find out more about Chappaquiddick Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chappaquiddick Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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