An aerial view of a coastal area with a lighthouse, a sandy beach, and a marina.

Chappaquiddick Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Chappaquiddick Island vacation rentals

A coastal hotel with multiple beachside rooms, a large covered area, and a beach with umbrellas.

1. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (370 reviews)
"The New Seabury resort is beautiful & has excellent customer service. The 4/5 stars is because the unit we stayed in needs some updating. However, the layout, cleanliness, & location is good."
United States
Kathleen
$215 nightly
The price is $246
Oct 11 - Oct 12
Total with taxes and fees
The Club at New Seabury
A modern living room with a sofa, chairs, a coffee table, and a dining area.

2. New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (90 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
$268 nightly
The price is $307
Sep 30 - Oct 1
Total with taxes and fees
New Seabury Cape Condo + Pool & Beach Escape
A boat docked at a concrete pier with a sandy shore in the background.

3. Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
Seconsett Island
10.0 out of 10, Exceptional, (44 reviews)
"Great stay!"
United States
Kian S.
$376 nightly
The price is $430
Sep 27 - Sep 28
Total with taxes and fees
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
A bedroom with a bed, a dresser, a sofa, and a painting on the wall.

4. Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and comfy place, a short drive to Falmouth center! Communication was very easy and check-in simple."
United States
Harry H.
$207 nightly
The price is $237
Sep 27 - Sep 28
Total with taxes and fees
Charming studio in tranquil Falmouth with AC
A living room with a flat-screen TV on a stand, a black leather chair, and a sofa. There are two windows with curtains, one of which offers a view of the sea.

5. 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, (96 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
$450 nightly
The price is $503
Oct 4 - Oct 5
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

6. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"This place was just what we needed! Would definitely stay again. Cozy and feels very homey! Thanks!"
United States
Chris S.
$711 nightly
The price is $794
Sep 27 - Sep 28
Total with taxes and fees
Oak Bluffs 4BR • 5 Min Drive to Downtown
A residential area with a well-maintained lawn, a stone retaining wall, and a two-story house with a blue door.

7. New 4 BR house near center and beaches with bikes

New 4 BR house near center and beaches with bikes
Katama
9.8 out of 10, Exceptional, (11 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
$1,235 nightly
The price is $1,380
Sep 27 - Sep 28
Total with taxes and fees
New 4 BR house near center and beaches with bikes
A modern kitchen with a large window overlooking a lake, a dining area with chairs, and a living room with a sofa.

8. WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
Sandwich
10.0 out of 10, Exceptional, (4 reviews)
"We really enjoyed our stay at this property. The view was amazing and had our own private beach to lounge at!"
United States
Sean H.
$378 nightly
The price is $433
Sep 27 - Sep 28
Total with taxes and fees
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
A deck with a fire pit, outdoor seating, and a blue umbrella.

9. Cozy Cottage walk to Menauhant Beach

Cozy Cottage walk to Menauhant Beach
East Falmouth
8.8 out of 10, Excellent, (8 reviews)
"It was a great weekend spot. Had everything we needed, nicely decorated, and in a great and private location"
United States
Grace P.
$625 nightly
The price is $716
Sep 30 - Oct 1
Total with taxes and fees
Cozy Cottage walk to Menauhant Beach
A view through a window with a wooden frame, overlooking a garden with various plants and a body of water in the background.

10. Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Tisbury
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful view of the lagoon; ideal place for a couple or single. Leisurely walk to town and close to public transportation."
United States
Adrienne W.
$443 nightly
The price is $495
Oct 12 - Oct 13
Total with taxes and fees
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
A modern kitchen with white cabinets, a central island with blue drawers, and stainless steel appliances.

11. Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (7 reviews)
"This is a new, beautiful and tastefully decorated 2 bedroom one bathroom house with a really nice big yard. Owner was very responsive and We had everything we needed for an enjoyable stay!"
United States
Elizabeth O.
$997 nightly
The price is $1,114
Oct 1 - Oct 2
Total with taxes and fees
Brand New Guest house
A wide sandy beach with footprints leading to the water, a clear sky, and distant buildings.

12. Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Barnstable
9.0 out of 10, Wonderful, (11 reviews)
"Nice location, quiet neighborhood, comfortable, and clean with a feeling of newness. Nice time of year to enjoy the porch and there was plenty of room for our group of seven. Three couches in the basement! Easy to get to town or beaches, etc. Host was helpful and communicative."
United States
Jen M.
$425 nightly
The price is $470
Sep 27 - Sep 28
Total with taxes and fees
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
A compact living space with a kitchen, dining area, and seating area.

13. 1 Mi to Ferry: 'Sea Street Cottage' in Hyannis

1 Mi to Ferry: 'Sea Street Cottage' in Hyannis
Hyannis
9.0 out of 10, Wonderful, (22 reviews)
"Perfect weekend getaway- super location. Cozy spot! Loved the area "
United States
Jill S.
$306 nightly
The price is $350
Oct 2 - Oct 3
Total with taxes and fees
1 Mi to Ferry: 'Sea Street Cottage' in Hyannis
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

14. Walk to Beach & Lighthouse: Oak Bluffs Studio!

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
8.0 out of 10, Very good, (11 reviews)
"The unit was clean and sufficient for 2 people. Outside could use some attention."
United States
Donna R.
$530 nightly
The price is $592
Sep 29 - Sep 30
Total with taxes and fees
Walk to Beach & Lighthouse: Oak Bluffs Studio!
A beach with a boat labeled MS1284HB and a covered area.

15. Secluded-Entire 2nd floor Suite with Private Bath

Secluded-Entire 2nd floor Suite with Private Bath
Barnstable
9.2 out of 10, Wonderful, (5 reviews)
"Great, very close to downtown hyannis. Charming and a nice owner. "
United States
sam s.
$198 nightly
The price is $227
Sep 27 - Sep 28
Total with taxes and fees
Secluded-Entire 2nd floor Suite with Private Bath

16. Charming Guesthouse | Walk to Beach | Downtown

Charming Guesthouse | Walk to Beach | Downtown
Falmouth
10.0 out of 10, Exceptional, (1 review)
"The house was very convenient to the beach, Aldi’s, Walmart, and local restaurants & shops. I wasn’t sure how private it was being a guest house, but I never felt that we didn’t have privacy. Our dogs enjoyed the little fenced in yard. We appreciated the updated bathroom and kitchen. The weather was so pleasant a small outdoor area would have been nice, and we missed not having a washer & dryer and dishwasher, but overall it was clean and cozy. We would stay there again! We loved the Cape,...
United States
Kandy W.
$530 nightly
The price is $607
Sep 28 - Sep 29
Total with taxes and fees
Charming Guesthouse | Walk to Beach | Downtown
A beach with a sandy shore and calm water.

17. Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
Oak Bluffs
8.8 out of 10, Excellent, (9 reviews)
"Loved our little cottage"
United States
Linda T.
$750 nightly
The price is $838
Sep 28 - Sep 29
Total with taxes and fees
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
A circular stone patio with Adirondack chairs and a small table in a forested area.

18. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
6.6 out of 10, (11 reviews)
"We had a perfect pre-/off-season stay with plenty of sleeping space. The location is fantastic—right between Vineyard Haven and Edgartown—making it easy to bike to both, plus there’s a beach across the street. The WiFi wasn’t working when we first arrived, but the owner was incredibly responsive and went above and beyond to fix it quickly. We’ll definitely be back!"
United States
Bethann N.
$604 nightly
The price is $675
Sep 29 - Sep 30
Total with taxes and fees
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

19. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (9 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
$1,154 nightly
The price is $1,289
Oct 1 - Oct 2
Total with taxes and fees
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A modern living room with a grey sofa, a wooden coffee table, and a television mounted on the wall.

20. LUX on Main | Downtown | Parking | Sleeps 6, #201

LUX on Main | Downtown | Parking | Sleeps 6, #201
Falmouth
10.0 out of 10, Exceptional, (6 reviews)
"This was the perfect location for our Cape Cod getaway. It was very central to everything we were doing while down there, very effortless to get to Martha’s Vineyard as well! The location was perfect with a bunch of different restaurants, shops and other stores all in walking distance. We will definitely consider staying here again in the future!"
United States
Zack D.
$655 nightly
The price is $750
Sep 28 - Sep 29
Total with taxes and fees
LUX on Main | Downtown | Parking | Sleeps 6, #201
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

Summercamp

Summercamp

10/10 Excellent
"Great, A+!"
Brendan 2-night trip
Posted 2 hours ago
Summercamp

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 $246 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

At Expedia, we put the best Chappaquiddick Island vacation 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 vacation.

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.

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