Chappaquiddick Island Holiday Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
1 Sept - 2 Sept
Tomorrow
2 Sept - 3 Sept
This weekend
5 Sept - 7 Sept
Next weekend
12 Sept - 14 Sept

Holiday Rentals in Chappaquiddick Island

Charming 2-bedroom house on Chappy with pool, Tennis, pickleball, WiFi and AC
Outdoor dining

Charming 2-bedroom house on Chappy with pool, Tennis, pickleball, WiFi and AC

10.0 out of 10, Exceptional, (1)
"Awesome house, very comfortable and a lot of fun. Thanks so much for the hospitality!!"
Charming 2-bedroom house on Chappy with pool, Tennis, pickleball, WiFi and AC
Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach
Property grounds

Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach

10.0 out of 10, Exceptional, (33)
"We loved our stay here. It is a private and peaceful location. Christian was a great and responsive host. The house was exactly as listed and very comfortable and clean."
Chappaquiddick retreat-outdoor shower, hot-tub, decks, central AC-close to beach
The Club at New Seabury
Private beach nearby, beach bar

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (327)
"Nice amenities. "
The Club at New Seabury
InnSeason Resorts Captain's Quarters
On the beach, white sand

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (176)
"Just a quick weekend away. Great location for beach lovers. Also excellent retaurants "
InnSeason Resorts Captain's Quarters
Sea Mist Resort
Exterior

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (135)
"Great resort with suites, very cosy with great amenities, close to excellent beach and shopping."
The price is HK$1,116
HK$1,278 total
includes taxes & fees
30 Sept - 1 Oct
Sea Mist Resort
Steps to the Ocean! Perfect Location!!!
Beach nearby, sun-loungers

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (219)
"Perfect for a couple and two kids"
Steps to the Ocean! Perfect Location!!!
Coastal chic meets French Provençal in this newly renovated oceanfront home.
5 bedrooms, desk, iron/ironing board, travel cot

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (85)
"Great stay! "
The price is HK$4,670
HK$10,073 total
includes taxes & fees
30 Sept - 1 Oct
Coastal chic meets French Provençal in this newly renovated oceanfront home.
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Outdoor dining

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

10.0 out of 10, Exceptional, (162)
"Beautiful cottage , great location. Would love to stay again "
The price is HK$5,798
HK$9,385 total
includes taxes & fees
26 Sept - 27 Sept
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Steps to the beach with an ocean view,
On the beach, sun-loungers, beach towels

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (127)
"Nice home, great views and very relaxing stay."
Steps to the beach with an ocean view,
Beachside Village Resort
Seasonal outdoor pool

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (99)
"Great location! Nice property! "
Beachside Village Resort
Beautifully Renovated Main Street Cottage- Great Location
Exterior

Beautifully Renovated Main Street Cottage- Great Location

10.0 out of 10, Exceptional, (118)
"We were thrilled to arrive at our property with everything as pictured but actually more charming in person. It is easily walkable to town and restaurants. Communication with the owner was easy and I can recommend it to anyone who wants to stay on Nantucket. "
Beautifully Renovated Main Street Cottage- Great Location
Charming 2-bedroom cottage with AC, WiFi in serene Barnstable
Property grounds

Charming 2-bedroom cottage with AC, WiFi in serene Barnstable

10.0 out of 10, Exceptional, (3)
"This was the perfect home base for our Cape weekend! The host was responsive, the space was clean, and everything was easily accessible. "
Charming 2-bedroom cottage with AC, WiFi in serene Barnstable
Renovated Cottage off Main Street- Great Location
Exterior

Renovated Cottage off Main Street- Great Location

10.0 out of 10, Exceptional, (158)
"The cabin was perfect. It was on more of a busy road than we anticipated, but everything else was wonderful. We enjoyed ourselves so much!!"
Renovated Cottage off Main Street- Great Location
Love Sand, Madaket on the Beach , Lovely Seaside Home
Exterior

Love Sand, Madaket on the Beach , Lovely Seaside Home

10.0 out of 10, Exceptional, (52)
"We thoroughly enjoyed our two nights and are sad to leave. The property is iconically Nantucket. Its location - and the views- is spectacular. It is well equipped for a relaxing family or couples vacation. Hope we can make it back. "
The price is HK$5,519
HK$11,878 total
includes taxes & fees
29 Sept - 30 Sept
Love Sand, Madaket on the Beach , Lovely Seaside Home
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath
Beach nearby

Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

8.6 out of 10, Excellent, (21)
"So turn key and perfect for Month, Joy is an exceptional host and I’d recommend her place anytime"
The price is HK$624
HK$1,384 total
includes taxes & fees
2 Sept - 3 Sept
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath
Southcape Resort Mashpee a Ramada by Wyndham
Exterior

Southcape Resort Mashpee a Ramada by Wyndham

3.0 star property
8.6 out of 10, Excellent, (201)
"Enjoyed our stay."
Southcape Resort Mashpee a Ramada by Wyndham
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
TV, DVD player

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.4 out of 10, (26)
"The property is quiet, spacious and was within a walkable mile of downtown Oak Bluffs. The beds were comfortable. Plenty of clean linens and towels. The house could use some updating. The coffee maker, drinking glasses, and silverware need to be replaced with cleaner ones. And the torn portions of the sectional couch should be fixed. I would definitely stay at the property again."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Smart TV

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

9.4 out of 10, Exceptional, (84)
"Close to buses, restaurants and ferries. 10/10, we would stay again."
The price is HK$2,339
HK$4,171 total
includes taxes & fees
1 Oct - 2 Oct
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..
Property grounds

Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..

8.6 out of 10, Excellent, (46)
"Great place for a summer vacation"
Renovated Nantucket Style 2 Bed/2 Bath Cottage, Steps to Private Beach, Market..
The Costal Corner - Martha's Vineyard
Microwave, oven, stovetop, dishwasher

The Costal Corner - Martha's Vineyard

2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was great for our golf trip. The 3 bedrooms were exceptional "
The Costal Corner - Martha's Vineyard
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
Sign in
Sign up, it's free

Top Chappaquiddick Island Hotel Reviews

Find out more about Chappaquiddick Island

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!