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. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (366 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 NZ$494
includes taxes & fees
7 Sept - 8 Sept
The Club at New Seabury

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 NZ$583
includes taxes & fees
2 Sept - 3 Sept
New Seabury Cape Condo + Pool & Beach Escape

3. Lovely two bedroom apartment with indoor fireplace

Lovely two bedroom apartment with indoor fireplace
Oak Bluffs
10.0 out of 10, Exceptional, (7 reviews)
"Great stay, flexible and responsive host. Difficult location, however, as it was not centrally located or easy to access transportation, etc."
United States
Aviva M.
The price is NZ$1,250
includes taxes & fees
7 Sept - 8 Sept
Lovely two bedroom apartment with indoor fireplace

4. Make Lasting Memories In This Adorable Vineyard Cottage!

Make Lasting Memories In This Adorable Vineyard Cottage!
Oak Bluffs
9.8 out of 10, Exceptional, (154 reviews)
"Cute, compact, and had everything we needed for ourstay. I'd definitely stay there again."
United States
Karen C.
The price is NZ$834
includes taxes & fees
2 Sept - 3 Sept
Make Lasting Memories In This Adorable Vineyard Cottage!

5. 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 NZ$1,208
includes taxes & fees
25 Aug - 26 Aug
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

6. Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
10.0 out of 10, Exceptional, (1 review)
"Wonderful host to work with!"
United States
Jocelyn J.
The price is NZ$377
includes taxes & fees
25 Aug - 26 Aug
Charming studio in tranquil Falmouth with AC

7. 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$1,412
includes taxes & fees
9 Sept - 10 Sept
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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, (8 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is NZ$2,423
includes taxes & fees
9 Sept - 10 Sept
New 4 BR house near center and beaches with bikes

9. 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, (95 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
The price is NZ$1,141
includes taxes & fees
8 Sept - 9 Sept
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

10. Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Tisbury
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful view of the lagoon; ideal place for a couple or single. Leisurely walk to town and close to public transportation."
United States
Adrienne W.
The price is NZ$981
includes taxes & fees
1 Sept - 2 Sept
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

11. Walk to Town/Golf Club - Renovated Edgartown Home

Walk to Town/Golf Club - Renovated Edgartown Home
Edgartown
10.0 out of 10, Exceptional, (47 reviews)
"Great house in a great location—just a short, easy walk to downtown Edgartown"
United States
Steven M.
The price is NZ$1,916
includes taxes & fees
2 Sept - 3 Sept
Walk to Town/Golf Club - Renovated Edgartown Home

12. 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 NZ$1,731
includes taxes & fees
8 Sept - 9 Sept
Brand New Guest house

13. Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt

Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
Oak Bluffs
10.0 out of 10, Exceptional, (47 reviews)
"Great accommodations and a perfect location for the beach, shopping and great food."
United States
Hugh M.
The price is NZ$1,228
includes taxes & fees
1 Sept - 2 Sept
Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt

14. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is NZ$1,590
includes taxes & fees
9 Sept - 10 Sept
Charming Vacation Home in Oak Bluffs.

15. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (29 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is NZ$2,056
includes taxes & fees
6 Sept - 7 Sept
The Seashell Cove - Martha's Vineyard

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, (8 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is NZ$2,345
includes taxes & fees
9 Sept - 10 Sept
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

17. Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool
Chilmark
9.6 out of 10, Exceptional, (22 reviews)
"This is a great property for an individual or a couple looking to explore the island!"
United States
Jillian G.
The price is NZ$886
includes taxes & fees
10 Sept - 11 Sept
Cozy efficiency apartment/heated pool

18. Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people

Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people
Barnstable
8.6 out of 10, Excellent, (30 reviews)
"It was very comfortable with upgraded kitchen and bathroom. It had all we needed. The owner was very responsive . Easy check in process. The location was perfect, just across from a beautiful ocean beach and very near Hyannis and many attractions. "
United States
Helene M.
The price is NZ$907
includes taxes & fees
19 Aug - 20 Aug
Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people

19. 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 NZ$458
includes taxes & fees
13 Sept - 14 Sept
Secluded-Entire 2nd floor Suite with Private Bath
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chappaquiddick Island holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chappaquiddick Island. 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 Chappaquiddick Island. 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 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 holiday 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 Chappaquiddick Island short-term rentals, that won’t be hard to do.

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