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

Chappaquiddick Island Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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, (368 reviews)
"A"
United States
Zachary
The price is CA $300
CA $344 total
includes taxes & fees
Sep 28 - Sep 29
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, (90 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
The price is CA $123
CA $450 total
includes taxes & fees
Sep 30 - Oct 1
New Seabury Cape Condo + Pool & Beach Escape

3. 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, (96 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
The price is CA $420
CA $747 total
includes taxes & fees
Oct 4 - Oct 5
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

4. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
10.0 out of 10, Exceptional, (31 reviews)
"This property is quiet yet close enough to the business areas. Very clean, well maintained lovely unit with balcony. The host Joziane commutated with us from minutes after the booking to the end of stay, very helpful."
United States
Unspecified U.
The price is CA $499
CA $915 total
includes taxes & fees
Sep 26 - Sep 27
Brand new! Lovely apartment-Vineyard Haven

5. 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, (10 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 CA $406
CA $730 total
includes taxes & fees
Oct 12 - Oct 13
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

6. 4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4 Mi to Bristol Beach! Coastal Retreat w/ Pond
East Falmouth
9.6 out of 10, Exceptional, (4 reviews)
"Oh were we ever excited to check-in to this Cape Cod style charming house! . It made us feel like we were Definitely visiting "The Cap"!. The decor was so nice and the outside patio area so comfortable. The location turned out to be perfect. We were concerned at first since we did not know the area but once we were out & about we realized we were in a good spot and on a beautiful street."
United States
Joyce G.
4 Mi to Bristol Beach! Coastal Retreat w/ Pond

7. Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (7 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 $504
CA $1,339 total
includes taxes & fees
Oct 1 - Oct 2
Brand New Guest house

8. 4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4 Mi to Bristol Beach! Coastal Retreat w/ Pond
3.0 star property
East Falmouth
4 Mi to Bristol Beach! Coastal Retreat w/ Pond

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

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
8.0 out of 10, Very good, (11 reviews)
"Very good experience Very clean owner very helpful My second time here"
United States
Diana
The price is CA $460
CA $867 total
includes taxes & fees
Sep 23 - Sep 24
Walk to Beach & Lighthouse: Oak Bluffs Studio!

10. Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
Oak Bluffs
8.8 out of 10, Excellent, (9 reviews)
"Loved our little cottage"
United States
Linda T.
The price is CA $552
CA $1,241 total
includes taxes & fees
Sep 28 - Sep 29
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

11. Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
10.0 out of 10, Exceptional, (3 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 $214
CA $323 total
includes taxes & fees
Oct 4 - Oct 5
Charming studio in tranquil Falmouth with AC

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, (11 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is CA $741
CA $2,044 total
includes taxes & fees
Sep 23 - Sep 24
New 4 BR house near center and beaches with bikes

13. 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, (43 reviews)
"Great stay!"
United States
Kian S.
The price is CA $245
CA $640 total
includes taxes & fees
Oct 1 - Oct 2
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

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

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
The price is CA $502
CA $1,177 total
includes taxes & fees
Sep 28 - Sep 29
Oak Bluffs 4BR • 5 Min Drive to Downtown

15. Cozy Cottage walk to Menauhant Beach

Cozy Cottage walk to Menauhant Beach
East Falmouth
8.8 out of 10, Excellent, (8 reviews)
"It was a great weekend spot. Had everything we needed, nicely decorated, and in a great and private location"
United States
Grace P.
The price is CA $268
CA $1,068 total
includes taxes & fees
Sep 30 - Oct 1
Cozy Cottage walk to Menauhant Beach

16. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
The price is CA $544
CA $1,289 total
includes taxes & fees
Sep 29 - Sep 30
Walk to Beach! Oak Bluffs Home & Studio

17. 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, (9 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
The price is CA $557
CA $1,905 total
includes taxes & fees
Oct 1 - Oct 2
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

18. 1 Mi to Ferry: 'sea Street Cottage' in Hyannis

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
8.0 out of 10, Very good, (1 review)
"The cottage is in a great location close to Main Street and the harbor. Easy parking at the cottage and it’s in a walkable area. Decor is cute and nautical, but it does feel like the cottage is missing a few things. It sleeps 4, but there is not enough seating for 4 in the living room. An additional comfortable chair would be nice. A stackable washer and dryer would also be great, but there is very little space for anything- we even had trouble finding spots for our luggage. The fridge door...
United States
Christa
The price is CA $239
CA $509 total
includes taxes & fees
Oct 2 - Oct 3
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

19. 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 $256
CA $571 total
includes taxes & fees
Oct 14 - Oct 15
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

20. 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 $275
CA $903 total
includes taxes & fees
Sep 23 - Sep 24
Charming Guesthouse | Walk to Beach | Downtown
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.
Save an average of 15% on thousands of hotels when you're signed in

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.

Explore a world of travel with Expedia