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

Holiday Rentals in Chappaquiddick Island

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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, (371 reviews)
"The New Seabury resort is beautiful & has excellent customer service. The 4/5 stars is because the unit we stayed in needs some updating. However, the layout, cleanliness, & location is good."
United States
Kathleen
The price is €150
includes taxes & fees
8 Nov - 9 Nov
The Club at New Seabury

2. 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, (99 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
The price is €434
includes taxes & fees
8 Nov - 9 Nov
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

3. Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard

Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard
Oak Bluffs
The price is €257
includes taxes & fees
10 Nov - 11 Nov
Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard

4. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"This place was just what we needed! Would definitely stay again. Cozy and feels very homey! Thanks!"
United States
Chris S.
The price is €607
includes taxes & fees
11 Nov - 12 Nov
Oak Bluffs 4BR • 5 Min Drive to Downtown

5. Vineyard Luxury "Yurt"

Vineyard Luxury "Yurt"
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"The yurt was clean and nice and served all of our needs."
United States
David C.
Vineyard Luxury "Yurt"

6. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is €762
includes taxes & fees
8 Nov - 9 Nov
Walk to Beach! Oak Bluffs Home & Studio

7. 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, (11 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 €462
includes taxes & fees
12 Nov - 13 Nov
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

8. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (31 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is €1,080
includes taxes & fees
18 Nov - 19 Nov
The Seashell Cove - Martha's Vineyard

9. 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, (45 reviews)
"Great place with kayaks and paddle boards, beach, close to Mashpee Commons. Host was great and place was clean and quaint."
United States
Michele M.
The price is €398
includes taxes & fees
8 Nov - 9 Nov
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

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

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
7.6 out of 10, Good, (14 reviews)
"The unit was clean and sufficient for 2 people. Outside could use some attention."
United States
Donna R.
The price is €343
includes taxes & fees
8 Nov - 9 Nov
Walk to Beach & Lighthouse: Oak Bluffs Studio!

11. 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, (98 reviews)
"Great location. Clear instructions"
United States
Sherise M.
The price is €424
includes taxes & fees
7 Nov - 8 Nov
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

12. 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, (13 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is €1,477
includes taxes & fees
15 Nov - 16 Nov
New 4 BR house near center and beaches with bikes

13. 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, (227 reviews)
"Great location "
United States
Stephanie B.
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

14. Coastal chic meets French Provençal in this newly renovated oceanfront home.

Coastal chic meets French Provençal in this newly renovated oceanfront home.
East Falmouth
10.0 out of 10, Exceptional, (101 reviews)
"Great views, beautiful setting . Scott was so attentive and easy to work with. We had a great time!"
United States
Ben L.
The price is €869
includes taxes & fees
19 Nov - 20 Nov
Coastal chic meets French Provençal in this newly renovated oceanfront home.

15. < 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 €817
includes taxes & fees
7 Nov - 8 Nov
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

16. Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
10.0 out of 10, Exceptional, (4 reviews)
"Very clean and comfy place, a short drive to Falmouth center! Communication was very easy and check-in simple."
United States
Harry H.
The price is €210
includes taxes & fees
8 Nov - 9 Nov
Charming studio in tranquil Falmouth with AC

17. Charming Guesthouse | Walk to Beach | Downtown

Charming Guesthouse | Walk to Beach | Downtown
Falmouth
10.0 out of 10, Exceptional, (1 review)
"The house was very convenient to the beach, Aldi’s, Walmart, and local restaurants & shops. I wasn’t sure how private it was being a guest house, but I never felt that we didn’t have privacy. Our dogs enjoyed the little fenced in yard. We appreciated the updated bathroom and kitchen. The weather was so pleasant a small outdoor area would have been nice, and we missed not having a washer & dryer and dishwasher, but overall it was clean and cozy. We would stay there again! We loved the Cape,...
United States
Kandy W.
The price is €511
includes taxes & fees
7 Nov - 8 Nov
Charming Guesthouse | Walk to Beach | Downtown

18. Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops
Falmouth
10.0 out of 10, Exceptional, (19 reviews)
"Jessica was absolutely amazing and so was the house! We stayed here for our family vacation and it was perfect. 5 stars all around!"
United States
Kelsey B.
The price is €734
includes taxes & fees
1 Dec - 2 Dec
Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

19. Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
10.0 out of 10, Exceptional, (3 reviews)
"Brenda and Derek were amazing hosts. They have a beautifully landscaped property with all the amenities needed for a relaxing family vacation. They are super responsive and take a lot of pride in giving their guests a top-notch experience. We will definitely consider staying at their properties again."
United States
Lamar A.
The price is €2,757
includes taxes & fees
30 Nov - 1 Dec
Beautiful Estate with salt water pool & pond with kayaks

20. Love Sand, Madaket on the Beach, Lovely Seaside Home

Love Sand, Madaket on the Beach, Lovely Seaside Home
Nantucket
9.8 out of 10, Exceptional, (58 reviews)
"Almost 270 degree views of the ocean — spectacular setting with lots of privacy, great amenities and miles of beach to explore. Very accessible to town. We loved our stay!"
United States
Marjorie A.
The price is €794
includes taxes & fees
16 Nov - 17 Nov
Love Sand, Madaket on the Beach, Lovely Seaside Home
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chappaquiddick Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chappaquiddick Island holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chappaquiddick Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chappaquiddick Island holiday rentals we have selected for you start as low as €150 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chappaquiddick Island rentals

At Expedia, we put the best Chappaquiddick Island holiday 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 holiday.

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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