Discover a selection of 1,000 vacation rentals in Chappaquiddick Island that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and air conditioning. Prices start at $188 per night, and houses and cottages are popular options for a stay in Chappaquiddick Island. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Chappaquiddick Island
Destination guide

Discover unspoiled Chappaquiddick Island

A little-developed spot situated east of historic Edgartown on Martha's Vineyard, Chappaquiddick Island serves up the chance to enjoy a truly unhurried getaway in the delightful Cape Cod region. Connected for much of the time to Martha's Vineyard by a narrow barrier beach between Katama and Wasque, and served by tiny 3-car ferries, travelers come to this isolated island to hike and cycle amid beautiful nature preserves, and to visit its tranquil Japanese garden. Chappaquiddick Island vacation rentals are small in number but big in character, offering travelers the perfect opportunity to enjoy this unspoiled destination.

Things to do

A touch of Japan on Chappaquiddick Island

A highlight for many visitors to Chappy is a wander through the Mytoi Japanese Garden, a tranquil 14-acre spot about 3 miles from the ferry port. Open daily from sunrise to sunset, this beautiful botanical garden counts walking trails and fragrant flower gardens among its highlights, though the star turn is Poucha Pond, a serene water feature where a quaint footbridge leads past the turtles and frogs in the water to a tiny island that's perfect for meditating. Parking is limited to just 15 cars, so it pays to be up and out of your rental nice and early if you plan to drive.


Exploring Chappaquiddick Island

A stay on Chappaquiddick Island, lovingly referred to by locals simply as "Chappy", offers a bit of peace and quiet in an otherwise frenzied world. Days here are often best spent on the seat of a bicycle, though you'll need to bring your own as the only commerce here is a small shop selling little more than milk. If you'd like someone in the know to show you around, Cape Poge tours, comprising a visit to the island's lighthouse and a spot of kayaking and seaside exploration, run daily from Memorial Day through to Columbus Day. Reservations are essential.


When to visit Chappaquiddick Island

Chappaquiddick Island vacation rentals are available all year round, but if you crave a little sun, the best month to visit is July, when you can expect the temperature to hover around 70 degrees and you'll avoid the patches of rain that typically arrive in August. Crowds are rarely an issue on the island, though if you plan to spend time exploring the attractions on Martha's Vineyard, you can expect a fair few people to be doing the same over the summer months. The fall months of September and October can be a good time to visit if you're hoping for a great deal on your rental.

Natural features

Natural appeal on Chappaquiddick Island

Miles of quiet paths flanked by overhanging trees, rugged beaches and more than 1,000 acres of preserved land makes a trip to Chappy a real treat for nature lovers. During your break in a Chappaquiddick Island vacation rental, be sure to head to the island's east where a pristine barrier island extends from Wasque Point to Cape Poge Gut. Along the way, a gull rookery and clusters of oystercatchers and piping plovers make Cape Poge Elbow particularly revered for its birdwatching opportunities. At Cape Poge Bay, striped bass and bluefish provide anglers with plenty of opportunities to reel in the catch of the day.

How to get there

Traveling to and around Chappaquiddick Island

The nearest airport is in Vineyard Haven, MA (MVY-Martha's Vineyard), located 7.4 mi (11.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Hyannis, MA (HYA-Barnstable Municipal), which is 21.7 mi (35 km) away.

How many vacation rentals are available around Chappaquiddick Island?

Our 2021 property listings offer a large selection of 779 vacation rentals around Chappaquiddick Island. From 686 house rentals to 55 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.