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, (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 CA $242
CA $277 total
includes taxes & fees
Nov 2 - Nov 3
The Club at New Seabury

2. 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 CA $157
CA $370 total
includes taxes & fees
Nov 11 - Nov 12
Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard

3. 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 CA $215
CA $535 total
includes taxes & fees
Nov 1 - Nov 2
Walk to Beach & Lighthouse: Oak Bluffs Studio!

4. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
10.0 out of 10, Exceptional, (34 reviews)
"Fabulous property! Clean and very comfy."
United States
Claudia
Brand new! Lovely apartment-Vineyard Haven

5. 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 CA $377
CA $662 total
includes taxes & fees
Nov 1 - Nov 2
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

6. 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 CA $226
CA $337 total
includes taxes & fees
Nov 2 - Nov 3
Charming studio in tranquil Falmouth with AC

7. 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.
The price is CA $395
CA $734 total
includes taxes & fees
Nov 11 - Nov 12
Vineyard Luxury "Yurt"

8. 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 CA $220
CA $613 total
includes taxes & fees
Nov 5 - Nov 6
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

9. WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
Sandwich
10.0 out of 10, Exceptional, (4 reviews)
"We really enjoyed our stay at this property. The view was amazing and had our own private beach to lounge at!"
United States
Sean H.
The price is CA $210
CA $549 total
includes taxes & fees
Nov 2 - Nov 3
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

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, (11 reviews)
"Cute, Cozy, comfortable, clean and quiet small apartment with full kitchen, a comfortable king bed with views of the lake from the kitchen/living room area and bedroom. It also had a nice spot outside on a deck with two chairs and table where we read, and watched the boats go by! Our host Stephen was very nice and helpful he responded quickly to our texts! The apt is near the bus route which is fabulous on the vineyard it goes to all the major spots you’d want to go! And it’s free!! It is also...
United States
Liz C.
The price is CA $419
CA $712 total
includes taxes & fees
Nov 8 - Nov 9
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

11. 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 CA $253
CA $835 total
includes taxes & fees
Nov 5 - Nov 6
Charming Guesthouse | Walk to Beach | Downtown

12. 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 CA $376
CA $1,015 total
includes taxes & fees
Nov 11 - Nov 12
Oak Bluffs 4BR • 5 Min Drive to Downtown

13. LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Nantucket Town
10.0 out of 10, Exceptional, (202 reviews)
"Great stay again"
United States
Ray S.
The price is CA $314
CA $751 total
includes taxes & fees
Nov 14 - Nov 15
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

14. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
7.0 out of 10, Good, (12 reviews)
"Loved this spot. Perfect central island location. Fantastic owner with an incredible response time. Would recommend this property to all5 stars"
United States
Eli R.
The price is CA $368
CA $860 total
includes taxes & fees
Nov 1 - Nov 2
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

15. 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 CA $330
CA $1,251 total
includes taxes & fees
Nov 16 - Nov 17
Love Sand, Madaket on the Beach, Lovely Seaside Home

16. Wilton Home - Sunny Retreat, Bike to Beach, Central AC

Wilton Home - Sunny Retreat, Bike to Beach, Central AC
Barnstable
The price is CA $152
CA $715 total
includes taxes & fees
Nov 10 - Nov 11
Wilton Home - Sunny Retreat, Bike to Beach, Central AC

17. Charming 3-bedroom house in lovely Barnstable

Charming 3-bedroom house in lovely Barnstable
Barnstable
9.6 out of 10, Exceptional, (5 reviews)
"Excellent stay! Loved the home! "
United States
Cailee B.
Charming 3-bedroom house in lovely Barnstable

18. 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, (225 reviews)
"Great location "
United States
Stephanie B.
The price is CA $252
CA $731 total
includes taxes & fees
Nov 5 - Nov 6
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

19. 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, (10 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

20. Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach

Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach
Sandwich
The price is CA $279
CA $549 total
includes taxes & fees
Nov 2 - Nov 3
Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach
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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