Holiday Rentals in Chappaquiddick Island

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Holiday Rentals in Chappaquiddick Island

Our top choices for Chappaquiddick Island holiday rentals

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

10.0 out of 10, Exceptional, (35)
"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

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

9.0 out of 10, Wonderful, (4)
"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

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (178)
"Great location and helpful staff"
InnSeason Resorts Captain's Quarters

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (333)
"Very relaxing, loved the different clubs available; beach, pool, tennis, playground for the little ones, bars and food. Some shops were closed due to being off season, but still enjoyed our stay. Looking forward to booking again "
The Club at New Seabury

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

10.0 out of 10, Exceptional, (85)
"Great stay! "
The price is €934
includes taxes & fees
30 Sept - 1 Oct
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (129)
"The house is a perfect place to stay. Close to the beach and the town of Hyannis. An ideal location for discovering the Cape Cod area. We felt relaxed and comfortable when we were there."
Steps to the beach with an ocean view,

Sea Mist Resort

3.0 star property
8.6 out of 10, Excellent, (136)
"Great resort with suites, very cosy with great amenities, close to excellent beach and shopping."
The price is €139
includes taxes & fees
30 Sept - 1 Oct
Sea Mist Resort

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (223)
"Perfect for a couple and two kids"
Steps to the Ocean! Perfect Location!!!

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

10.0 out of 10, Exceptional, (168)
"Beautiful cottage , great location. Would love to stay again "
The price is €670
includes taxes & fees
12 Oct - 13 Oct
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

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

6.4 out of 10, (30)
"The weather was perfect and our crew made the best of our trip."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

9.4 out of 10, Exceptional, (88)
"The location of this property cannot be beat! Our second time staying here."
The price is €482
includes taxes & fees
1 Oct - 2 Oct
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

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

9.4 out of 10, Exceptional, (89)
"Close to buses, restaurants and ferries. 10/10, we would stay again."
The price is €433
includes taxes & fees
1 Oct - 2 Oct
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Renovated Cottage off Main Street- Great Location

10.0 out of 10, Exceptional, (159)
"Super cute place and close to town! Really responsive host. We enjoyed our stay. "
Renovated Cottage off Main Street- Great Location

Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

10.0 out of 10, Exceptional, (110)
"Great outdoor spaces. Loved the kayaks, beach and fire pit. Our 2 year old grandson loved the outdoor shower. Our dog had a ball chasing squirrels in the fenced backyard. We would definitely stay again. Close to everything in Falmouth including Woodneck beach, our low tide favorite. "
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (99)
"Great location! Nice property! "
Beachside Village Resort

Love Sand, Madaket on the Beach, Lovely Seaside Home

10.0 out of 10, Exceptional, (54)
"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 €711
includes taxes & fees
25 Sept - 26 Sept
Love Sand, Madaket on the Beach, Lovely Seaside Home

The Costal Corner - Martha's Vineyard

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

Gorgeous Cottage steps from the beach

8.4 out of 10, Very good, (22)
"Location to town & beach was great. Cottage was listed accurate online. Communication with owner was welcoming. The cottage was a nice weekend get away."
Gorgeous Cottage steps from the beach

Cozy Beach Cottage

10.0 out of 10, Exceptional, (53)
"This was the perfect property for our visit to Martha’s Vineyard. The owners were so responsive and gave us a seamless experience. I would definitely stay at the Cozy Cottage again! "
Cozy Beach Cottage

Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK

8.6 out of 10, Excellent, (64)
"This property is wonderful. It is situated at the end of a very quiet dead-end street, right on the water. The home was extremely clean and nicely furnished. The kitchen was well appointed and had everything that you need for a family vacation."
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK
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

Find out more about Chappaquiddick Island

Everything you need to know about Chappaquiddick Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chappaquiddick Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chappaquiddick Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chappaquiddick Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chappaquiddick Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chappaquiddick Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chappaquiddick Island holiday rentals we have selected for you start as low as €139 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chappaquiddick Island rentals

At Expedia, we put the best Chappaquiddick Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chappaquiddick Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chappaquiddick Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chappaquiddick Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.