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Chappaquiddick Island Vacation Rentals

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In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Chappaquiddick Island vacation rentals

Private beach nearby, beach bar
The Club at New Seabury

Condo resort in New Seabury

3.5 star property
9.0 out of 10, Wonderful, (339)
"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 "
United States
Jose O.
$136 nightly
The price is $156
Dec 28 - Dec 29
Total with taxes and fees
The Club at New Seabury
On the beach, white sand
InnSeason Resorts Captain's Quarters

Aparthotel in Falmouth Heights

3.5 star property
9.8 out of 10, Exceptional, (192)
"Great property! Would definitely stay again."
United States
Brad
$125 nightly
The price is $142
Dec 15 - Dec 16
Total with taxes and fees
InnSeason Resorts Captain's Quarters
Fridge, microwave, oven, stovetop
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

Vacation Home in Barnstable

10.0 out of 10, Exceptional, (30)
"House is beautiful and well equipped, and located in a lovely quiet neighborhood. Host was quickly responsive to all of our inquiries. Overall a great spot for a family vacation. "
United States
Sheila B.
$851 nightly
The price is $974
Dec 11 - Dec 12
Total with taxes and fees
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
Fridge, microwave, oven, stovetop
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

Vacation Home in New Seabury

10.0 out of 10, Exceptional, (8)
"Nice house! Great area. Close to nice beach !"
United States
Cally G.
$954 nightly
The price is $1,092
Dec 11 - Dec 12
Total with taxes and fees
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
Dining
Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !

Vacation Home in Barnstable

10.0 out of 10, Exceptional, (1)
"My family and I thoroughly enjoyed our week long stay at the beautiful property. There were 12 of us and we were extremely comfortable, with plenty of space to gather and sleep. The property sits on a quiet pond, that was perfect for swimming and canoeing. We had our own little piece of paradise. There are canoes for use, several decks for lounging and was within a short distance to various shops and a grocery store just a few minutes away. The host was in constant contact with us, making sure...
United States
Madilynn B.
$891 nightly
The price is $1,019
Dec 11 - Dec 12
Total with taxes and fees
Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !
Interior
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Vacation Home in Oak Bluffs

10.0 out of 10, Exceptional, (7)
"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.
$1,053 nightly
The price is $1,176
Dec 11 - Dec 12
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Property grounds
Remodeled historical Gosnold Cottage.300 yards to the beach.

Vacation Home in HYANNIS

10.0 out of 10, Exceptional, (8)
"Place was beautiful and immaculate. We really enjoyed our stay. "
United States
Cathy G.
$657 nightly
The price is $752
Dec 11 - Dec 12
Total with taxes and fees
Remodeled historical Gosnold Cottage.300 yards to the beach.
Family House, Private Bathroom, Pool View | Shared kitchen
Sal's Place

Vacation Home in Hyannis

2.0 star property
$400 nightly
The price is $440
Dec 11 - Dec 12
Total with taxes and fees
Sal's Place
Outdoor dining
Spacious Lake House for Large Groups w Private Acre+ short path to Lake

Vacation Home in Barnstable

9.0 out of 10, Wonderful, (4)
"Had a great stay here - the hosts were flexible with our early check in and made the whole trip a smooth process! "
United States
Ally D.
$951 nightly
The price is $1,088
Dec 11 - Dec 12
Total with taxes and fees
Spacious Lake House for Large Groups w Private Acre+ short path to Lake
Paper towels
Hyannis Hideaway in Cape Cod

Vacation Home in Barnstable

10.0 out of 10, Exceptional, (2)
"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.
$545 nightly
The price is $623
Dec 11 - Dec 12
Total with taxes and fees
Hyannis Hideaway in Cape Cod
Pool
Great Harbors Summer Home

Vacation Home in Falmouth

$982 nightly
The price is $1,150
Jan 1 - Jan 2, 2026
Total with taxes and fees
Great Harbors Summer Home
Outdoor pool, a heated pool
Cozy efficiency apartment/heated pool

Apartment in Chilmark

9.6 out of 10, Exceptional, (21)
"We loved this property and would love to return!"
United States
Clifford L.
$410 nightly
The price is $458
Dec 31 - Jan 1, 2026
Total with taxes and fees
Cozy efficiency apartment/heated pool
Beach
Secluded-Entire 2nd floor Suite with Private Bath

Apartment in Barnstable

10.0 out of 10, Exceptional, (1)
"Great, very close to downtown hyannis. Charming and a nice owner. "
United States
sam s.
$149 nightly
The price is $171
Dec 14 - Dec 15
Total with taxes and fees
Secluded-Entire 2nd floor Suite with Private Bath
Exterior
Falmouth Oasis

Vacation Home in Falmouth

2.0 star property
$381 nightly
The price is $436
Dec 11 - Dec 12
Total with taxes and fees
Falmouth Oasis
5 bedrooms, desk, iron/ironing board, travel crib
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Vacation Home in East Falmouth

10.0 out of 10, Exceptional, (88)
"Great stay! "
United States
Michael M.
$781 nightly
The price is $893
Dec 11 - Dec 12
Total with taxes and fees
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Beach nearby
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Vacation Home in Barnstable

8.6 out of 10, Excellent, (8)
"This was an amazing property and our host was awesome and checked in to make sure everything was going well. Would definitely stay here again! Thank you! "
United States
Kim
$470 nightly
The price is $521
Dec 16 - Dec 17
Total with taxes and fees
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Terrace/patio
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Vacation Home in Barnstable

10.0 out of 10, Exceptional, (4)
"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.
$583 nightly
The price is $667
Dec 11 - Dec 12
Total with taxes and fees
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
Fridge, microwave, oven, stovetop
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Vacation Home in Tisbury

10.0 out of 10, Exceptional, (16)
"The house is clean, peaceful and perfectly appointed with everything you need for a great week on the Vineyard."
United States
Celeste P.
$971 nightly
The price is $1,085
Dec 23 - Dec 24
Total with taxes and fees
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Interior
Cape Cod Escape at Casa de Leo!

Vacation Home in Falmouth

2.5 star property
$1,228 nightly
The price is $1,405
Dec 11 - Dec 12
Total with taxes and fees
Cape Cod Escape at Casa de Leo!
Fridge, oven, stovetop, dishwasher
Sal's Place-Close to Tourism, Private Yard, Pool!

Vacation Home in Barnstable

$317 nightly
The price is $363
Dec 11 - Dec 12
Total with taxes and fees
Sal's Place-Close to Tourism, Private Yard, Pool!
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

Mansion House Inn And Spa

Mansion House Inn And Spa

10/10 Excellent
"Warm and friendly greeting at Front Desk. Room was clean and inviting- nice surprise!"
Thomas 1-night trip
Posted 2 days ago
Mansion House Inn And Spa

Find out more about Chappaquiddick Island

Everything you need to know about Chappaquiddick Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chappaquiddick Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chappaquiddick Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chappaquiddick Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $142 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chappaquiddick Island rentals

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