Chappaquiddick Island Holiday Rentals

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Holiday Rentals in Chappaquiddick Island

The Club at New Seabury

3.5 star property
Mashpee
9.0 out of 10, Wonderful, (336)
"Great stay! Didn't notice it being dated or dirty at all like some reviews said. We loved it!"
United States
Rachael
The Club at New Seabury

Water Access 5-bed 2-bath Retreat

2.0 star property
Hyannis
The price is NZ$1,674
includes taxes & fees
17 Nov - 18 Nov
Water Access 5-bed 2-bath Retreat

Sal's Place

2.0 star property
Hyannis
The price is NZ$1,021
includes taxes & fees
20 Nov - 21 Nov
Sal's Place

Secluded-Entire 2nd floor Suite with Private Bath

Barnstable
10.0 out of 10, Exceptional, (1)
"Great, very close to downtown hyannis. Charming and a nice owner. "
United States
sam s.
The price is NZ$281
includes taxes & fees
15 Nov - 16 Nov
Secluded-Entire 2nd floor Suite with Private Bath

The Seashell Cove - Martha's Vineyard

Katama
9.8 out of 10, Exceptional, (23)
"My family and I had a great stay in this lovely home!! The house had everything we needed and was a great starting point for all island adventures. Charles was so helpful throughout the entire trip. We would most certainly stay here again!"
United States
Caryn I.
The price is NZ$1,014
includes taxes & fees
8 Dec - 9 Dec
The Seashell Cove - Martha's Vineyard

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

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
The price is NZ$918
includes taxes & fees
19 Nov - 20 Nov
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

Nantucket Town
10.0 out of 10, Exceptional, (176)
"Great place to stay! Walking distance to town and lovely yard to relax in."
United States
Danielle J.
The price is NZ$880
includes taxes & fees
1 Dec - 2 Dec
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

Love Sand, Madaket on the Beach, Lovely Seaside Home

Nantucket
10.0 out of 10, Exceptional, (55)
"Beautiful location. Views are amazing and the sound from the ocean so soothing!"
United States
Jennifer M.
The price is NZ$1,718
includes taxes & fees
24 Nov - 25 Nov
Love Sand, Madaket on the Beach, Lovely Seaside Home

Newly Renovated Martha's Vineyard Vacation Rental!

Katama
9.6 out of 10, Exceptional, (47)
"Very nice house that served our needs. Well located. Nicely appointed. The bedroom downstairs with twin beds accommodated my elderly mother who has trouble with stairs. No real maintenance issues other than, the gfci outlets in the bathrooms did not work."
United States
Silvia B.
The price is NZ$1,051
includes taxes & fees
14 Nov - 15 Nov
Newly Renovated Martha's Vineyard Vacation Rental!

Hyannis Hideaway in Cape Cod

Barnstable
10.0 out of 10, Exceptional, (2)
"We had a great time at Hyannis Hideaway! The location was PERFECT! We were no more than 6 minutes to the beach. 2 minutes from stores and restaurants! AC units in every room to keep us cool. The house was so clean and spacious for our big group. We can’t wait to go back!"
United States
Ashleigh I.
The price is NZ$1,099
includes taxes & fees
24 Nov - 25 Nov
Hyannis Hideaway in Cape Cod

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

Oak Bluffs
9.4 out of 10, Exceptional, (88)
"We loved our stay! It was the perfect location, loved the view, it was sparce but clean. Check in/out was easy and owner was responsive. "
United States
Tracy M.
The price is NZ$880
includes taxes & fees
14 Nov - 15 Nov
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Charming studio in tranquil Falmouth with AC

Falmouth
The price is NZ$366
includes taxes & fees
25 Nov - 26 Nov
Charming studio in tranquil Falmouth with AC

Nantucket - edge of town

Nantucket
9.6 out of 10, Exceptional, (88)
"Very easy, comfortable and accessible to beaches and town!"
United States
Jacqueline D.
The price is NZ$857
includes taxes & fees
1 Dec - 2 Dec
Nantucket - edge of town

Cape Cod Hyannis Rendezvous'

Barnstable
9.8 out of 10, Exceptional, (6)
"We enjoyed our stay. The house was spotless -- in fact, it seems like it was newly renovated which was delightful. Each room was comfortable and cozy and had its own TV, an amenity we really appreciated.Perhaps this is coming, but the addition of some mirrors in the bedrooms or hall , and a dining table to play games and have family meals on would be great. Again, we really enjoyed our stay."
United States
Valerie O.
The price is NZ$1,086
includes taxes & fees
24 Nov - 25 Nov
Cape Cod Hyannis Rendezvous'

3-bedroom house in charming Barnstable with WiFi, AC,Walking distance to Main st

Barnstable
10.0 out of 10, Exceptional, (1)
"Excellent property with a great location"
United States
David B.
The price is NZ$654
includes taxes & fees
1 Dec - 2 Dec
3-bedroom house in charming Barnstable with WiFi, AC,Walking distance to Main st

Remodeled historical Gosnold Cottage.300 yards to the beach.

HYANNIS
10.0 out of 10, Exceptional, (8)
"We had an outstanding time at this property. It was as advertised and for a cottage, the amenities were new and worked well. The location is quiet and removed from the road with easy parking. We had no problems during our time and the owner was easily reachable. "
United States
Mark
The price is NZ$1,328
includes taxes & fees
14 Nov - 15 Nov
Remodeled historical Gosnold Cottage.300 yards to the beach.

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

Falmouth
10.0 out of 10, Exceptional, (207)
"The house was even nicer than the pictures. We came in March for a long weekend with some friends and had a really great time. Walking distance to so many fun things- great house for all ages!"
United States
Briget R.
The price is NZ$876
includes taxes & fees
16 Nov - 17 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Spring Escape in Hatchville – Sleeps 6 + Dogs!

Falmouth
10.0 out of 10, Exceptional, (11)
"We LOVED our stay. The home is gorgeous and comfortable with everything we needed. The kids loved the game barn. Nicely located. We loved the deck. Would stay again!"
United States
Enid G.
The price is NZ$1,275
includes taxes & fees
14 Nov - 15 Nov
Spring Escape in Hatchville – Sleeps 6 + Dogs!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Oak Bluffs
10.0 out of 10, Exceptional, (7)
"This home is truly that, a welcoming escape nestled in the woods. It’s elevated beach-style furnishings feel hand-picked. We traveled with a 14 month old — the house had high-quality baby must haves, pack and play and high chair. We had the pleasure of a responsive host and caretaker. Close to trails, YMCA and the island’s top attractions … !highly recommend!"
United States
Kerry-Ann H.
The price is NZ$2,141
includes taxes & fees
21 Nov - 22 Nov
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Barnstable
10.0 out of 10, Exceptional, (4)
"Great property for families- loved the downstairs pool table and outside area with fire pit and volleyball net. Super clean. Highly recommend. "
United States
Erica C.
The price is NZ$1,179
includes taxes & fees
15 Nov - 16 Nov
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
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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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, 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 NZ$880 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.