Chappaquiddick Island Vacation Rentals from CA $190: Short-Term Rentals for 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chappaquiddick Island vacation rentals

A golf course with a clubhouse, a lake, and surrounding trees.

1. The Club at New Seabury

New Seabury

Kathleen

CA $236 total

includes taxes & fees

Nov 9 - Nov 10

A room with a view of the sea through large windows, a wooden deck, and a pier with structures.

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

Oak Bluffs

Cassandra

CA $680 total

includes taxes & fees

Nov 8 - Nov 9

3. Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard

Oak Bluffs

CA $392 total

includes taxes & fees

Nov 10 - Nov 11

A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

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

Oak Bluffs

Chris S.

CA $942 total

includes taxes & fees

Nov 13 - Nov 14

A modern kitchen with a large island, a dining area with a table and chairs, and a view of a green garden through large windows.

5. Vineyard Luxury "Yurt"

Oak Bluffs

David C.

CA $612 total

includes taxes & fees

Nov 10 - Nov 11

An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

6. Walk to Beach! Oak Bluffs Home & Studio

Oak Bluffs

CA $1,172 total

includes taxes & fees

Nov 9 - Nov 10

A view through a window with a wooden frame, overlooking a garden with various plants and a body of water in the background.

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

Tisbury

Adrienne W.

A spacious living area with wooden beams, a dining table, and a sofa.

8. The Seashell Cove - Martha's Vineyard

Katama

Eric C.

CA $1,483 total

includes taxes & fees

Nov 8 - Nov 9

A boat docked at a concrete pier with a sandy shore in the background.

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

Seconsett Island

Michele M.

CA $613 total

includes taxes & fees

Nov 9 - Nov 10

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

Oak Bluffs

Donna R.

CA $549 total

includes taxes & fees

Nov 22 - Nov 23

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

Oak Bluffs

Sherise M.

CA $678 total

includes taxes & fees

Nov 7 - Nov 8

A modern kitchen with white cabinetry, a dining area with a wooden table and white chairs, and a large window providing natural light.

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

Katama

Susan M.

CA $2,329 total

includes taxes & fees

Nov 16 - Nov 17

A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

13. Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Falmouth

Stephanie B.

CA $731 total

includes taxes & fees

Nov 9 - Nov 10

A covered outdoor seating area with a view of the ocean, a ceiling fan, and a flat-screen TV on the wall.

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

East Falmouth

Ben L.

CA $1,359 total

includes taxes & fees

Nov 19 - Nov 20

A spacious living room with a wooden staircase, a fireplace, and a leather sofa.

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

Oak Bluffs

"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...

Kate K.

CA $1,247 total

includes taxes & fees

Nov 9 - Nov 10

A bedroom with a bed, a dresser, a sofa, and a painting on the wall.

16. Charming studio in tranquil Falmouth with AC

Falmouth

Harry H.

CA $321 total

includes taxes & fees

Nov 8 - Nov 9

17. Charming Guesthouse | Walk to Beach | Downtown

Falmouth

"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,...

Kandy W.

CA $796 total

includes taxes & fees

Nov 7 - Nov 8

A spacious kitchen with a large island, wooden flooring, and a dining area with chairs and a table.

18. Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

Falmouth

Kelsey B.

CA $1,153 total

includes taxes & fees

Dec 1 - Dec 2

A two-story house with a stone facade, a covered patio, and a well-maintained garden.

19. Beautiful Estate with salt water pool & pond with kayaks

Oak Bluffs

Lamar A.

CA $4,233 total

includes taxes & fees

Nov 30 - Dec 1

A two-story house with a balcony, a front porch with columns, and a sign that reads 'LIVE SWIM'.

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

Nantucket

Marjorie A.

CA $1,250 total

includes taxes & fees

Nov 16 - Nov 17

View all properties

Find vacation rentals that suit your style

Top Chappaquiddick Island Hotel Reviews

A bedroom with a bed, bedside tables, a chair, a table, and a view of the outdoors.

The Coonamessett

Falmouth

10/10 Excellent

We stayed for 2 nights in early Aug 2015. When we checked in we were told we had an upgrade due to a large group staying at the hotel. We ended up with a huge suite! It was very quiet, peaceful and relaxing. There is a great restaurant and bar right in the inn and also a fun pub next door that features live music, lots of fun! The bed and linens were excellent and the room size was very large. A bit of a "grand old dame", but well-maintained and very clean. Staff helped with taking the...

HJTours Inc

A bedroom with a large bed, a view of the outdoors through sliding glass doors, and a balcony with a white railing.

Faraway Martha's Vineyard

Edgartown

10/10 Excellent

Alicia

A man sitting at a table with a laptop, overlooking a pool area with chairs and tables.

Hyannis Travel Inn

Hyannis

10/10 Excellent

The reviews are true, this is a great place to stay. We based ourselves here as we explored the Cape. It’s a 10 minute walk to the port where you catch the ferries to Nantucket and the Vineyard. Main st Hyannis is the next street over. You really can’t beat the location. The staff is friendly and extremely helpful. The breakfast was good and there was always plenty. The rooms are very basic, nothing fancy at all, no bells and whistles. Just a basic room with all the necessities for a decent...

Cristina

A large, multi-story house with a covered porch and a well-maintained lawn.

Shore Haven Inn

Falmouth

10/10 Excellent

Jamie

A two-story house with a brick pathway leading to the front door, surrounded by a well-maintained lawn and green Adirondack chairs.

The Franklin Hotel Martha's Vineyard

Edgartown

10/10 Excellent

Martha

A cozy, well-lit room with a fireplace, comfortable seating, and large windows offering views of the outdoors.

Nantucket Resort Collection

Nantucket Town

10/10 Excellent

My husband and I stayed at the Regatta Inn on Tuesday and Wednesday night, Oct 14 and 15. My husband treated me to this as a 40th anniversary gift. The staff were so helpful and nice, Sofia and Teasha. The room was very clean and well equipped. The bed, pillows and linens were top quality. We loved the breakfast offered and the cookies at 4 pm were really good. I would highly recomnend this hotel and if we return, hopefully, we will stay here again. Sofia also upgraded us from a queen room to a...

John

A modern hotel room with a large bed, a separate bathroom with a bathtub, and a blue rug.

Admiralty Inn & Suites - a Red Collection Hotel

East Falmouth

8/10 Good

Sherif

A spacious living room with a sofa, chairs, a coffee table, and a staircase.

Morgan Hotel

Oak Bluffs

10/10 Excellent

Fred Di

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chappaquiddick Island vacation rentals we have selected for you start as low as CA $190 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 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.

Chappaquiddick Island Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chappaquiddick Island vacation rentals

1. The Club at New Seabury

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

3. Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard

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

5. Vineyard Luxury "Yurt"

6. Walk to Beach! Oak Bluffs Home & Studio

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

8. The Seashell Cove - Martha's Vineyard

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

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

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

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

13. Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

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

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

16. Charming studio in tranquil Falmouth with AC

17. Charming Guesthouse | Walk to Beach | Downtown

18. Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

19. Beautiful Estate with salt water pool & pond with kayaks

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

Find vacation rentals that suit your style

Top Chappaquiddick Island Hotel Reviews

The Coonamessett

10/10 Excellent

Find out more about Chappaquiddick Island

Chappaquiddick Island vacation rentals: An excellent choice for every season

How to find incredible deals on Chappaquiddick Island rentals

Explore a world of travel with Expedia