Holiday Rentals in Chappaquiddick Island

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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 €906
includes taxes & fees
8 Feb - 9 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 €159
includes taxes & fees
15 Feb - 16 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, (197 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 €126
includes taxes & fees
8 Feb - 9 Feb
InnSeason Resorts Captain's Quarters

Sal's Place

Sal's Place
2.0 star property
Hyannis
The price is €491
includes taxes & fees
18 Feb - 19 Feb
Sal's Place

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 €172
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 €527
includes taxes & fees
28 Feb - 1 Mar
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

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 €966
includes taxes & fees
8 Feb - 9 Feb
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

Beautiful Home in Falmouth Village

Beautiful Home in Falmouth Village
Falmouth
10.0 out of 10, Exceptional, (10 reviews)
"Great house and good location. "
United States
Jeannie E.
Beautiful Home in Falmouth Village

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 €1,015
includes taxes & fees
8 Feb - 9 Feb
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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.
Love Sand, Madaket on the Beach, Lovely Seaside Home

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 €2,137
includes taxes & fees
8 Feb - 9 Feb
Beautiful 5BR with Pool. 3 Renovated Levels of Luxury. Walk to Town or 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 €451
includes taxes & fees
1 Mar - 2 Mar
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

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 €914
includes taxes & fees
8 Feb - 9 Feb
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Gorgeous home in town 3Bed 3 bath. screened porch- 3 levels of living & parking

Gorgeous home in town 3Bed 3 bath. screened porch- 3 levels of living & parking
Nantucket Town
10.0 out of 10, Exceptional, (40 reviews)
"Great house and location! Will definitely return. Has everything one needs at a rental property. "
United States
Debra D.
The price is €1,220
includes taxes & fees
8 Feb - 9 Feb
Gorgeous home in town 3Bed 3 bath. screened porch- 3 levels of living & parking

Cape Cod Escape at Casa de Leo!

Cape Cod Escape at Casa de Leo!
Falmouth
Cape Cod Escape at Casa de Leo!

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.
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

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 €548
includes taxes & fees
8 Feb - 9 Feb
Cape Cod Hyannis Rendezvous'

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 €419
includes taxes & fees
8 Feb - 9 Feb
Located Steps Away To Main Street And .7 Miles From Surf Drive 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 €567
includes taxes & fees
11 Feb - 12 Feb
Oak Bluffs - Quiet neighborhood

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 €532
includes taxes & fees
8 Feb - 9 Feb
Hyannis Hideaway in Cape Cod
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, 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 €126 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.