Chappaquiddick Island Holiday Rentals

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Holiday Rentals in Chappaquiddick Island

Sleeps 12, amazing view, tennis court, basketball court, beaches

Edgartown
9.6 out of 10, Exceptional, (40)
"It was a great place to hangout with family members. I lot of places to plop down with a book, a lot of things to do to keep people busy - just a great time."
United States
mark s.
Sleeps 12, amazing view, tennis court, basketball court, beaches

The Club at New Seabury

3.5 star property
Mashpee
9.0 out of 10, Wonderful, (336)
"Great stay! Didn't notice it being dated or dirty at all like some reviews said. We loved it!"
United States
Rachael
The Club at New Seabury

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

East Falmouth
10.0 out of 10, Exceptional, (88)
"This is a lovely property for a family beach vacation! The property has a wonderful view of the ocean, easy access to a beach, and is close to many great restaurants and things to do. Our host was very responsive and accommodating throughout our stay. I would highly recommend. "
United States
Andrew H.
The price is NZ$1,797
includes taxes & fees
8 Dec - 9 Dec
Coastal chic meets French Provençal in this newly renovated oceanfront home.

InnSeason Resorts Captain's Quarters

3.5 star property
Falmouth Heights
9.8 out of 10, Exceptional, (192)
"Absolutely beautiful room amenities and view. Hands down the best place we have ever stayed at on the Cape. Definitely going back!!"
United States
Keith
InnSeason Resorts Captain's Quarters

Sea Mist Resort

3.0 star property
Mashpee
8.6 out of 10, Excellent, (140)
"We had a fabulous visit!"
United States
Joelle
Sea Mist Resort

Steps to the Ocean! Perfect Location!!!

Barnstable
10.0 out of 10, Exceptional, (231)
"I absolutely loved my stay at this charming cottage in Hyannis! The place was cozy, spotless, and beautifully maintained. A perfect mix of comfort and Cape Cod charm. The location was great, close to the beach and local shops, yet quiet enough to relax and unwind."
United States
Maria
Steps to the Ocean! Perfect Location!!!

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

Nantucket Town
10.0 out of 10, Exceptional, (176)
"Great place to stay! Walking distance to town and lovely yard to relax in."
United States
Danielle J.
The price is NZ$880
includes taxes & fees
1 Dec - 2 Dec
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

Newly Renovated Near Amazing Sunset Beach

Falmouth
9.8 out of 10, Exceptional, (73)
"The house is beautiful. It looks just like the pictures. The area around the house is very safe and quiet. The owners are very responsive. They even provided beach towels (which might not be in the description). "
United States
Debbie B.
Newly Renovated Near Amazing Sunset Beach

Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

West Tisbury
9.0 out of 10, Wonderful, (35)
"The peaceful woodland setting is just beautiful! Enjoyed a quiet stay in this spacious one bedroom house. The porch wraps around entire house and gave our morning coffee and breakfast a very special vacation feel."
United States
Maryann B.
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

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

East Falmouth
10.0 out of 10, Exceptional, (112)
"The place was beautiful, clean, spacious and the perfect location. There were so many options, from hanging out on the porch, by the fire, on the water front, or inside around the upstairs living room/billiards area downstairs. The owner was an amazing communicator, as she answered all of my questions promptly. I highly recommend this place to anyone!Thank you for an awesome and memorable stay! "
United States
natalia A.
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

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

Oak Bluffs
6.4 out of 10, (31)
"indoor and outdoor comfortable space"
United States
Delores C.
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Cozy getaway in a central location w/ a full kitchen & furnished deck

Oak Bluffs
6.6 out of 10, (25)
"The home was nice, a little outdated, but great for a family. Unfortunately it does not have AC and when we arrived we found 2 fans were broken. We immediately contacted Vacasa who said they would send maintenance. While waiting for maintenance, we also noticed within the first hour that one of the dining chair backs was broken/not attached, one of the bed posts fell off as it was not attached, and the fan in one of the bathrooms was stuck on. We planned to notify maintenance when they came but...
United States
Dawn R.
Cozy getaway in a central location w/ a full kitchen & furnished deck

Beachside Village Resort

3.0 star property
Falmouth
9.4 out of 10, Exceptional, (101)
"Very clean and quiet place to relax. Very friendly and professional! We will come back!"
United States
Emmanuelle Loriot
Beachside Village Resort

The quintessential MV home. Now booking for 2026!

Oak Bluffs
9.8 out of 10, Exceptional, (55)
"Beautiful home on quiet street within walking distance to Oak Bluffs. Well equipped kitchen and comfy family room. Beautiful primary suite with huge modern bathroom. Carrington was an excellent host and very responsive to anything that came up. "
United States
Jenny D.
The quintessential MV home. Now booking for 2026!

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

Oak Bluffs
9.4 out of 10, Exceptional, (91)
"Location, the water view, delicious restaurants nearby. Apt was comfy, clean. For 1 night only used the fridge. "
United States
Brenda M.
The price is NZ$881
includes taxes & fees
15 Nov - 16 Nov
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Steps to the beach with an ocean view,

Barnstable
10.0 out of 10, Exceptional, (139)
"Great stay."
United States
Richard D.
Steps to the beach with an ocean view,

Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people

Barnstable
8.8 out of 10, Excellent, (28)
"Very positive experience! Just steps to the beach. Really enjoyed our stay!"
United States
MICHELLE V.
Oceanside Cottage condo next to beach 2bedroom 1bath for 4-6 people

Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach

2.0 star property
Falmouth
10.0 out of 10, Exceptional, (1)
"The location was great and the pullouts were comfortable. The only downside is the walk through bathroom."
United States
Matthew
Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach

Renovated Cottage off Main Street- Great Location

Nantucket Town
10.0 out of 10, Exceptional, (164)
"Super cute place and close to town! Really responsive host. We enjoyed our stay. "
United States
Taylor N.
Renovated Cottage off Main Street- Great Location

Gorgeous Spacious Victorian Cape Cod Beach View Retreat

Falmouth
10.0 out of 10, Exceptional, (16)
"The house is a wonderful place for a slow and relaxing holiday! Close to everything but tucked away from anything too busy. "
United States
Alexandra M.
Gorgeous Spacious Victorian Cape Cod Beach View Retreat
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

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, 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 NZ$880 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.