Chappaquiddick Island Holiday 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 holiday 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)
"The hosts are excellent people, great communicators who want VBRO guests to have an outstanding experience. Chappy is a wonderful retreat from the rest of the world. That is my only word of caution, it requires a ferry to eat out or shop. Otherwise this is a great place to read write meditate beach and let go of everyday worries. It has a higher price tag because your paying for a premium location, guest service experience and higher quality accomodation."
United States
SparkleCappy
The price is HK$5,522
HK$8,298 total
includes taxes & fees
18 Feb - 19 Feb
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, (349 reviews)
"Everything was superb, accommodations, check in service, check out service!!"
United States
Dianna
The price is HK$1,280
HK$1,465 total
includes taxes & fees
17 Feb - 18 Feb
The Club at New Seabury

InnSeason Resorts Captain's Quarters

InnSeason Resorts Captain's Quarters
3.5 star property
Falmouth Heights
9.8 out of 10, Exceptional, (199 reviews)
"This is my go to hotel when I’m in Falmouth. Always clean and the staff are very friendly. The one bedroom units are very nice!"
United States
Jeff
The price is HK$1,013
HK$1,160 total
includes taxes & fees
12 Feb - 13 Feb
InnSeason Resorts Captain's Quarters

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, (3 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 HK$1,300
HK$3,170 total
includes taxes & fees
19 Feb - 20 Feb
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette

Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
Falmouth
8.2 out of 10, Very good, (24 reviews)
"Wonderful stay, had everything we needed, Joy was very receptive to our messages. Thanks so much!"
United States
Alex K.
The price is HK$766
HK$1,566 total
includes taxes & fees
28 Feb - 1 Mar
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette

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)
"Property needs a refresh."
United States
Paul B.
The price is HK$2,345
HK$4,795 total
includes taxes & fees
14 Mar - 15 Mar
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

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, (56 reviews)
"We had an absolutely amazing stay at Love Sand. The views from every angle are breathtaking and the house is extremely comfortable. Definitely recommend renting a Wrangler (or other off road vehicle) . We're already looking at our calendars to book another stay! "
United States
Lilian D.
The price is HK$1,384
HK$6,381 total
includes taxes & fees
1 Mar - 2 Mar
Love Sand, Madaket on the Beach, Lovely Seaside Home

Falmouth Oasis

Falmouth Oasis
Falmouth
The price is HK$1,126
HK$3,499 total
includes taxes & fees
12 Feb - 13 Feb
Falmouth Oasis

Entire Hyannis Home Near Downtown & Beaches

Entire Hyannis Home Near Downtown & Beaches
Barnstable
The price is HK$903
HK$3,199 total
includes taxes & fees
26 Feb - 27 Feb
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, (212 reviews)
"This beautiful well-appointed home was the perfect spot for a girlfriend’s getaway. Walkable to the shops and restaurants, nice big rooms for chats, and a great kitchen island to congregate around for breakfast. We loved our time here!"
United States
Annemarie G.
The price is HK$1,267
HK$3,883 total
includes taxes & fees
12 Feb - 13 Feb
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

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, (91 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
The price is HK$2,345
HK$4,192 total
includes taxes & fees
1 Mar - 2 Mar
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Sal's Place

Sal's Place
2.0 star property
Hyannis
The price is HK$3,126
HK$4,516 total
includes taxes & fees
17 Feb - 18 Feb
Sal's Place

Beautiful 5BR with Pool. 3 Renovated Levels of Luxury. Walk to Town or Beach.

Beautiful 5BR with Pool. 3 Renovated Levels of Luxury. Walk to Town or Beach.
Nantucket
10.0 out of 10, Exceptional, (1 review)
"Wonderful house, plenty of space, gorgeous peaceful view out back. Very responsive host!"
United States
Leslie B.
The price is HK$11,723
HK$19,852 total
includes taxes & fees
24 Feb - 25 Feb
Beautiful 5BR with Pool. 3 Renovated Levels of Luxury. Walk to Town or Beach.

Oak Bluffs - Quiet neighborhood

Oak Bluffs - Quiet neighborhood
Oak Bluffs
9.4 out of 10, Exceptional, (43 reviews)
"perfect for our needs"
United States
Ed V.
The price is HK$2,345
HK$5,240 total
includes taxes & fees
20 Feb - 21 Feb
Oak Bluffs - Quiet neighborhood

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 HK$2,064
HK$5,226 total
includes taxes & fees
12 Feb - 13 Feb
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Spring Escape in Hatchville – Sleeps 6 + Dogs!

Spring Escape in Hatchville – Sleeps 6 + Dogs!
Falmouth
10.0 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay. Everything was clean and well kept. "
United States
Lynn S.
The price is HK$2,252
HK$5,709 total
includes taxes & fees
12 Feb - 13 Feb
Spring Escape in Hatchville – Sleeps 6 + Dogs!

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 HK$2,735
HK$6,984 total
includes taxes & fees
24 Feb - 25 Feb
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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 HK$2,625
HK$4,669 total
includes taxes & fees
12 Feb - 13 Feb
Hyannis Hideaway in Cape Cod

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 HK$4,918
HK$8,940 total
includes taxes & fees
15 Feb - 16 Feb
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

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 HK$3,908
HK$8,477 total
includes taxes & fees
24 Feb - 25 Feb
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
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

Search for holiday rentals in Chappaquiddick Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Chappaquiddick Island using one of the methods below:

  • View our selection of featured holiday rentals in Chappaquiddick Island
  • Use the map to find apartments and other holiday homes in the Chappaquiddick Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chappaquiddick Island while they last

Look no further and take a look at our great range of rental properties in Chappaquiddick Island!