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. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (365 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
$253 nightly
The price is $289
Sep 7 - Sep 8
Total with taxes and fees
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.
$308 nightly
The price is $352
Sep 2 - Sep 3
Total with taxes and fees
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.
$667 nightly
The price is $745
Sep 7 - Sep 8
Total with taxes and fees
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.
$457 nightly
The price is $510
Sep 2 - Sep 3
Total with taxes and fees
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.
$524 nightly
The price is $585
Sep 8 - Sep 9
Total with taxes and fees
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.
$175 nightly
The price is $200
Sep 11 - Sep 12
Total with taxes and fees
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.
$760 nightly
The price is $849
Sep 8 - Sep 9
Total with taxes and fees
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, (7 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
$1,292 nightly
The price is $1,443
Sep 7 - Sep 8
Total with taxes and fees
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, (94 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
$623 nightly
The price is $696
Sep 8 - Sep 9
Total with taxes and fees
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.
$479 nightly
The price is $535
Sep 2 - Sep 3
Total with taxes and fees
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.
$999 nightly
The price is $1,116
Sep 2 - Sep 3
Total with taxes and fees
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.
$914 nightly
The price is $1,021
Sep 7 - Sep 8
Total with taxes and fees
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.
$651 nightly
The price is $727
Aug 26 - Aug 27
Total with taxes and fees
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
$856 nightly
The price is $956
Sep 8 - Sep 9
Total with taxes and fees
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.
$1,072 nightly
The price is $1,197
Sep 6 - Sep 7
Total with taxes and fees
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, (7 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
$1,249 nightly
The price is $1,395
Sep 6 - Sep 7
Total with taxes and fees
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)
"We loved this property and would love to return!"
United States
Clifford L.
$485 nightly
The price is $542
Sep 8 - Sep 9
Total with taxes and fees
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.
$470 nightly
The price is $537
Aug 19 - Aug 20
Total with taxes and fees
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.
$232 nightly
The price is $266
Aug 24 - Aug 25
Total with taxes and fees
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

Everything you need to know about Chappaquiddick Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chappaquiddick Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chappaquiddick Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chappaquiddick Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chappaquiddick Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chappaquiddick Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $289 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chappaquiddick Island rentals

At Expedia, we put the best Chappaquiddick Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chappaquiddick Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chappaquiddick Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chappaquiddick Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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