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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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, (367 reviews)
"Overall, very good. Pool and beach area were not the most convenient to access. Short drive required."
United States
Grayson
$225 nightly
The price is $257
Sep 7 - Sep 8
Total with taxes and fees
The Club at New Seabury
A modern kitchen with a marble countertop, a central island, and a hanging light fixture.

2. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
9.8 out of 10, Exceptional, (30 reviews)
"Lovely and all brand new accommodation's that are clean and comfy! A quiet location too! "
United States
Nancy K.
$404 nightly
The price is $451
Sep 7 - Sep 8
Total with taxes and fees
Brand new! Lovely apartment-Vineyard Haven
A wooden deck with a white railing, two chairs, and a small table.

3. Make Lasting Memories In This Adorable Vineyard Cottage!

Make Lasting Memories In This Adorable Vineyard Cottage!
Oak Bluffs
9.8 out of 10, Exceptional, (155 reviews)
"Cute, compact, and had everything we needed for ourstay. I'd definitely stay there again."
United States
Karen C.
$457 nightly
The price is $510
Sep 2 - Sep 3
Total with taxes and fees
Make Lasting Memories In This Adorable Vineyard Cottage!
A gravel driveway leading to a house surrounded by trees and a garden.

4. Lovely two bedroom apartment with indoor fireplace

Lovely two bedroom apartment with indoor fireplace
Oak Bluffs
10.0 out of 10, Exceptional, (8 reviews)
"Great stay, flexible and responsive host. Difficult location, however, as it was not centrally located or easy to access transportation, etc."
United States
Aviva M.
$671 nightly
The price is $750
Sep 7 - Sep 8
Total with taxes and fees
Lovely two bedroom apartment with indoor fireplace
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, (94 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
$480 nightly
The price is $536
Sep 10 - Sep 11
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
A modern living room with a sofa, chairs, a coffee table, and a dining area.

6. New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (87 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
$295 nightly
The price is $338
Sep 2 - Sep 3
Total with taxes and fees
New Seabury Cape Condo + Pool & Beach Escape
A modern kitchen with white cabinets, a central island with blue drawers, and stainless steel appliances.

7. Brand New Guest house

Brand New Guest house
Oak Bluffs
10.0 out of 10, Exceptional, (6 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.
$912 nightly
The price is $1,019
Sep 7 - Sep 8
Total with taxes and fees
Brand New Guest house
A modern kitchen with white cabinets, a wooden dining table, and black chairs.

8. Walk to Town/Golf Club - Renovated Edgartown Home

Walk to Town/Golf Club - Renovated Edgartown Home
Edgartown
10.0 out of 10, Exceptional, (47 reviews)
"Great house in a great location—just a short, easy walk to downtown Edgartown"
United States
Steven M.
$945 nightly
The price is $1,055
Sep 2 - Sep 3
Total with taxes and fees
Walk to Town/Golf Club - Renovated Edgartown Home
A spacious living area with a high ceiling, a dining table, and a kitchen area.

9. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (9 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
$760 nightly
The price is $849
Sep 11 - Sep 12
Total with taxes and fees
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

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

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
8.4 out of 10, Very Good, (9 reviews)
"Very accommodating early check in and great communication "
United States
Katelyn K.
$557 nightly
The price is $622
Aug 31 - Sep 1
Total with taxes and fees
Walk to Beach & Lighthouse: Oak Bluffs Studio!
A view through a window with a wooden frame, overlooking a garden with various plants and a body of water in the background.

11. 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, (7 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.
$476 nightly
The price is $532
Sep 6 - Sep 7
Total with taxes and fees
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
A residential area with a well-maintained lawn, a stone retaining wall, and a two-story house with a blue door.

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

New 4 BR house near center and beaches with bikes
Katama
9.6 out of 10, Exceptional, (9 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
$1,293 nightly
The price is $1,444
Sep 7 - Sep 8
Total with taxes and fees
New 4 BR house near center and beaches with bikes
A bedroom with a bed, a dresser, a sofa, and a painting on the wall.

13. Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and comfy place, a short drive to Falmouth center! Communication was very easy and check-in simple."
United States
Harry H.
$181 nightly
The price is $208
Sep 23 - Sep 24
Total with taxes and fees
Charming studio in tranquil Falmouth with AC
A two-story house with a swimming pool, a covered patio, and a fenced backyard.

14. Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool
Chilmark
9.6 out of 10, Exceptional, (25 reviews)
"This is a great property for an individual or a couple looking to explore the island!"
United States
Jillian G.
$480 nightly
The price is $536
Sep 28 - Sep 29
Total with taxes and fees
Cozy efficiency apartment/heated pool
A cozy living room with a wooden ceiling, a stone fireplace, a leather sofa, and a dining area with a table and chairs.

15. < 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
Oak Bluffs
7.4 out of 10, Good, (3 reviews)
"House was neat architectural wise and family history of home ownership was very cool. However, listing noted there was a washer/dryer and there was not. House also noted that there was a fire pit and it was rusted through. Screen door handles were broken, windows need repair, and house has animals living in the downstairs bathroom wall. House needs updates to charge what was being charged a night. In addition, there was a Nor’easter that hit the island and we attempted to contact the host to let...
United States
Kate K.
$710 nightly
The price is $793
Aug 31 - Sep 1
Total with taxes and fees
< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs
A circular stone patio with Adirondack chairs and a small table in a forested area.

16. 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.
$635 nightly
The price is $709
Aug 31 - Sep 1
Total with taxes and fees
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A beach with large rocks and waves.

17. Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!

Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!
Oak Bluffs
9.8 out of 10, Exceptional, (59 reviews)
"We had the best girls weekend here! The space was perfect size for us. Great spaces for sitting and chatting, both inside and on the balcony. The location was perfect, right across from the ocean waves and shells on the beach. Walking distance to town and easy access to biking. It had everything we needed."
United States
Rachael C.
$824 nightly
The price is $920
Sep 24 - Sep 25
Total with taxes and fees
Beautiful Beachfront “Oasis by the Sea” in the Heart of Oak Bluffs!
A spacious living area with wooden beams, a dining table, and a sofa.

18. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (29 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
$1,080 nightly
The price is $1,206
Sep 6 - Sep 7
Total with taxes and fees
The Seashell Cove - Martha's Vineyard
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, (8 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
$1,251 nightly
The price is $1,397
Sep 7 - Sep 8
Total with taxes and fees
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

20. Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
$742 nightly
The price is $829
Sep 27 - Sep 28
Total with taxes and fees
Charming Vacation Home in Oak Bluffs.
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

Comfort Inn Hyannis - Cape Cod

Comfort Inn Hyannis - Cape Cod

8/10 Good
"The bathroom needed some renovations it was not in a better condition"
Olwethu 1-night trip
Posted 1 hour ago
Comfort Inn Hyannis - Cape Cod

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 $257 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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