Chappaquiddick Island Vacation Rentals

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Our top choices for Chappaquiddick Island vacation rentals

Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!

Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!
Edgartown
9.8 out of 10, Exceptional, (16 reviews)
"Overall great experience"
United States
Scott P.
The price is CA $962
CA $1,445 total
includes taxes & fees
May 9 - May 10
Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (355 reviews)
"Our stay was great and Amy at the front desk is a god send she was absolutely the best."
United States
Jasmine
The price is CA $315
CA $361 total
includes taxes & fees
May 11 - May 12
The Club at New Seabury

Sea Mist Resort

Sea Mist Resort
3.0 star property
Mashpee
8.6 out of 10, Excellent, (154 reviews)
"Yes, everything was great in the property and its surroundings."
United States
Nilza
Sea Mist Resort

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

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
The price is CA $195
CA $494 total
includes taxes & fees
May 31 - Jun 1
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
New Seabury
8.6 out of 10, Excellent, (91 reviews)
"This was the perfect home for our weekend getaway! Joyce was wonderful to work with. Perfect location and beautiful home, just what we needed!"
United States
Courtney R.
The price is CA $408
CA $843 total
includes taxes & fees
May 9 - May 10
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Nantucket - edge of town

Nantucket - edge of town
Nantucket
9.6 out of 10, Exceptional, (89 reviews)
"Host was very responsive and helpful. Great location. "
United States
Barbara Z.
The price is CA $295
CA $722 total
includes taxes & fees
May 10 - May 11
Nantucket - edge of town

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
10.0 out of 10, Exceptional, (7 reviews)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
United States
Swathanthra M.
The price is CA $749
CA $1,649 total
includes taxes & fees
May 10 - May 11
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (26 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is CA $612
CA $1,130 total
includes taxes & fees
May 10 - May 11
The Seashell Cove - Martha's Vineyard

Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is CA $543
CA $1,128 total
includes taxes & fees
May 27 - May 28
Charming Vacation Home in Oak Bluffs.

New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
Barnstable
10.0 out of 10, Exceptional, (31 reviews)
"It was a great stay and clean home. Recommend people to stay here"
United States
Charbel T.
The price is CA $953
CA $1,690 total
includes taxes & fees
May 10 - May 11
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Tisbury
10.0 out of 10, Exceptional, (16 reviews)
"We had an amazing time at this beautiful home. Great, clean space to spend an evening visit with friends and family. Great location with easy access around the island. Would highly recommend! "
United States
Jennifer T.
The price is CA $682
CA $1,479 total
includes taxes & fees
May 8 - May 9
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

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, (88 reviews)
"The location of this property cannot be beat! Our second time staying here."
United States
Ashley S.
The price is CA $552
CA $902 total
includes taxes & fees
May 8 - May 9
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Edgartown Designer Cottage between Town & Beach.

Edgartown Designer Cottage between Town & Beach.
Katama
10.0 out of 10, Exceptional, (25 reviews)
"Wonderful week in MV! The cottage had everything we needed and was a great location to bike into town or to the beach. Would love to come back and stay again!"
United States
Lauren B.
The price is CA $456
CA $895 total
includes taxes & fees
May 10 - May 11
Edgartown Designer Cottage between Town & Beach.

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 $293
CA $651 total
includes taxes & fees
Jun 4 - Jun 5
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

Waterfront Gem: Hot Tub, Fire Pit & Private Beach! 3 Bed, 1.5 Baths, Sleeps 6

Waterfront Gem: Hot Tub, Fire Pit & Private Beach! 3 Bed, 1.5 Baths, Sleeps 6
Popponesset
10.0 out of 10, Exceptional, (188 reviews)
"great stay! fantastic location."
United States
Emily P.
The price is CA $680
CA $1,496 total
includes taxes & fees
May 23 - May 24
Waterfront Gem: Hot Tub, Fire Pit & Private Beach! 3 Bed, 1.5 Baths, Sleeps 6

Sal's Place

Sal's Place
2.0 star property
Hyannis
The price is CA $802
CA $1,081 total
includes taxes & fees
May 10 - May 11
Sal's Place

Waterfront Hyannis Home Near Ferry

Waterfront Hyannis Home Near Ferry
Barnstable
9.4 out of 10, Exceptional, (11 reviews)
"Walk to Hyannis restaurants & bars. Walk to ferry. "
United States
Dina M.
The price is CA $393
CA $957 total
includes taxes & fees
May 10 - May 11
Waterfront Hyannis Home Near Ferry

Beach Pass Included!

Beach Pass Included!
Barnstable
The price is CA $802
CA $1,049 total
includes taxes & fees
May 10 - May 11
Beach Pass Included!

Water Access 5-bed 2-bath Retreat

Water Access 5-bed 2-bath Retreat
2.0 star property
Hyannis
The price is CA $696
CA $1,441 total
includes taxes & fees
May 14 - May 15
Water Access 5-bed 2-bath Retreat

Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
New Seabury
10.0 out of 10, Exceptional, (8 reviews)
"Great place"
United States
Aaron Q.
The price is CA $856
CA $1,564 total
includes taxes & fees
May 10 - May 11
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to 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.