Search Vacation Homes in Chappaquiddick Island

  • 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 homes

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 AED 2,595
AED 3,900 total
includes taxes & fees
15 May - 16 May
Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!

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 AED 1,054
AED 2,257 total
includes taxes & fees
3 May - 4 May
Nantucket - edge of town

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Barnstable
8.6 out of 10, Excellent, (8 reviews)
"This was an amazing property and our host was awesome and checked in to make sure everything was going well. Would definitely stay here again! Thank you! "
United States
Kim
The price is AED 526
AED 1,871 total
includes taxes & fees
3 May - 4 May
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

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 AED 731
AED 2,585 total
includes taxes & fees
17 May - 18 May
Waterfront Gem: Hot Tub, Fire Pit & Private Beach! 3 Bed, 1.5 Baths, Sleeps 6

Charming 3 bed room with magnificent views & large deck

Charming 3 bed room with magnificent views & large deck
Barnstable
8.0 out of 10, Very Good, (3 reviews)
"We had a great stay in Hyannis! The location is great for catching a ferry to Nantucket or the vineyard, and Main Street is within walking distance. The backyard is also very peaceful for a cup of coffee in the morning! "
United States
Meghan H.
The price is AED 606
AED 1,564 total
includes taxes & fees
3 May - 4 May
Charming 3 bed room with magnificent views & large deck

Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is AED 1,466
AED 3,044 total
includes taxes & fees
26 May - 27 May
Charming Vacation Home in Oak Bluffs.

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 AED 2,020
AED 4,452 total
includes taxes & fees
7 May - 8 May
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Falmouth Oasis

Falmouth Oasis
Falmouth
The price is AED 661
AED 1,808 total
includes taxes & fees
6 May - 7 May
Falmouth Oasis

Entire Hyannis Home - Near Downtown & Beaches

Entire Hyannis Home - Near Downtown & Beaches
Barnstable
10.0 out of 10, Exceptional, (1 review)
"We had a fantastic stay! The property was extremely clean from top to bottom, which immediately made us feel comfortable settling in. The beds and linens were incredibly comfortable and we all slept great.The location was also a huge plus. It is close to great restaurants, local events and plenty to do in the area, making it easy to get around and enjoy everything nearby.The host was extremely communicative and responsive, which made the whole experience smooth and stress free from booking...
United States
Bethany P.
The price is AED 698
AED 1,850 total
includes taxes & fees
5 May - 6 May
Entire Hyannis Home - Near Downtown & Beaches

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, (216 reviews)
"Great place to stay for Christmas with our family. Cozy place with a convenient location. "
United States
Gail B.
The price is AED 735
AED 2,018 total
includes taxes & fees
19 May - 20 May
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Dream beach home on Lewis Bay with ocean views & amazing outdoor areas

Dream beach home on Lewis Bay with ocean views & amazing outdoor areas
West Yarmouth
Dream beach home on Lewis Bay with ocean views & amazing outdoor areas

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 AED 1,837
AED 3,984 total
includes taxes & fees
3 May - 4 May
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
The price is AED 826
AED 3,397 total
includes taxes & fees
10 May - 11 May
4-bedroom house in lovely Edgartown..Centrally located

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.4 out of 10, Exceptional, (3 reviews)
"This house was perfect for our getaway. Rebecca, the host, was extremely responsive and helpful during our trip. The house was as advertised. It was clean, well equipped, and the location was perfect as well "
United States
Louis R.
The price is AED 1,286
AED 3,249 total
includes taxes & fees
15 May - 16 May
A NOSTALGIC SPACE! 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 AED 2,479
AED 4,103 total
includes taxes & fees
3 May - 4 May
The Seashell Cove - Martha's Vineyard

Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
Barnstable
10.0 out of 10, Exceptional, (5 reviews)
"Very nice property in a quiet and convenient location. Private backyard with outdoor shower. Interior was completely updated with very nice furnishings and appliances. All in all a great home that we will definitely return to. "
United States
Jim C.
The price is AED 970
AED 2,451 total
includes taxes & fees
3 May - 4 May
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

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 AED 2,571
AED 4,561 total
includes taxes & fees
9 May - 10 May
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

Hyannis Hideaway in Cape Cod

Hyannis Hideaway in Cape Cod
Barnstable
10.0 out of 10, Exceptional, (2 reviews)
"Awesome private property, close to Main Street and Craigsville beach. My friends and I stay in Hyannis every 4th of July and this home was super accommodating for groups and close to everything. Great stay would recommend. "
United States
Hunter W.
The price is AED 1,306
AED 2,272 total
includes taxes & fees
3 May - 4 May
Hyannis Hideaway in Cape Cod

Oak Bluffs - Quiet neighborhood

Oak Bluffs - Quiet neighborhood
Oak Bluffs
9.4 out of 10, Exceptional, (43 reviews)
"Perfectly situated!"
United States
Damani B.
The price is AED 1,469
AED 2,929 total
includes taxes & fees
15 May - 16 May
Oak Bluffs - Quiet neighborhood

Cape Cod Hyannis Rendezvous'

Cape Cod Hyannis Rendezvous'
Barnstable
9.8 out of 10, Exceptional, (6 reviews)
"Nice stay close to town"
United States
Daniel m.
The price is AED 1,283
AED 2,250 total
includes taxes & fees
4 May - 5 May
Cape Cod Hyannis Rendezvous'
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