Choose from 47 vacation rentals located in Chappaquiddick Island, Massachusetts. Top filters in Chappaquiddick Island include Internet / Wifi, Kitchen / Kitchenette, and TV. Prices range from $247 to $10,000 per night. Our most popular vacation rental types near Chappaquiddick Island are Hotel and RV.

Top vacation rentals in Chappaquiddick Island

Living area
4.7
Outstanding(34 Reviews)
House
 in Edgartown
Sleeps 12, amazing view, tennis court, basketball court, beaches
12 guests · 6 bedrooms · 5 baths
Garden · Pets allowed · Kitchen / Kitchenette

Nestled in Chappaquiddick Island, this House is perfect for your next vacation. Enjoy Sleeps 12, amazing view, tennis court, basketball court, beaches's top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
vrbo logo
View deal
Lounge on the private wrap-around deck.
4.8
Outstanding(37 Reviews)
House
 in Edgartown
BEST OF CHAPPY-SPECTACULAR WATERVU --FERRY TX-WALK/BCH- KAYAKS/BIKES -3 WKS LEFT
8 guests · 4 bedrooms · 3 baths
Garden · Kitchen / Kitchenette · Internet / Wifi

Are you ready to indulge in a relaxing getaway? Our House in Chappaquiddick Island has everything you need for a rejuvenating stay. Treat yourself to BEST OF CHAPPY-SPECTACULAR WATERVU --FERRY TX-WALK/BCH- KAYAKS/BIKES -3 WKS LEFT's exceptional amenities, such as Dishwasher, Internet / Wifi and Laundry.

$$$$
vrbo logo
View deal
Front of house
5.0
Outstanding(27 Reviews)
House
 in Chappaquiddick
Luxury Chappaquiddick Getaway with Oceanviews
8 guests · 4 bedrooms · 3 baths
Garden · Kitchen / Kitchenette · Air conditioner

Looking for a House in Chappaquiddick Island, this House for $635 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

$$$$
vrbo logo
View deal
View from the deck
short walk to the beach
5.0
Outstanding(28 Reviews)
House
 in Edgartown
Classic Chappy Beach House, big water views, near the water
8 guests · 4 bedrooms · 1 bath
Garden · Pets allowed · Kitchen / Kitchenette

Experience vacation in Chappaquiddick Island with our House, Classic Chappy Beach House, big water views, near the water. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal

Search by property type

Search by amenity

Explore vacation rentals with the most popular amenities in Chappaquiddick Island

Vacation rentals with internet & wifi in Chappaquiddick Island

Welcome!
4.7
Outstanding(13 Reviews)
House
 in Edgartown
Oceanviews, Walk to Beaches, Nature Preserves,
8 guests · 4 bedrooms · 3 baths
Garden · Kitchen / Kitchenette · Internet / Wifi

Experience the best of Chappaquiddick Island with this House available for $605. This property is equipped with amenities including Dishwasher, Internet / Wifi and Laundry, and more.

$$$$
vrbo logo
View deal
Cape Poge, Chappaquiddick
4.8
Outstanding(13 Reviews)
Cottage
 in Edgartown
Chappy relaxation and fun!
5 guests · 2 bedrooms · 3 baths
Garden · Kitchen / Kitchenette · Internet / Wifi

Cottage in Chappaquiddick Island, for $330 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
Sitting Room with fireplace
5.0
Outstanding(17 Reviews)
House
 in Edgartown
Beautiful Post and Beam. Built in 2013. Sleeps 6-8
8 guests · 3 bedrooms · 4 baths
Garden · Kitchen / Kitchenette · Internet / Wifi

Business stays, family stays, couples stay, getaway vacation, and rental in Chappaquiddick Island at Beautiful Post and Beam. Built in 2013. Sleeps 6-8 for $464 for your next trip.

$$$$
vrbo logo
View deal
Beautiful designer kitchen with stainless appliances
4.9
Outstanding(12 Reviews)
House
 in Edgartown
Newly Renovated Chappy House with State of the Art Living ,
8 guests · 3 bedrooms · 2 baths
Pets allowed · Kitchen / Kitchenette · Internet / Wifi

Nestled in Chappaquiddick Island, this House is perfect for your next vacation. Enjoy Newly Renovated Chappy House with State of the Art Living ,'s top-rated amenities, including Dishwasher, Internet / Wifi and Laundry, and more.

$$$$
vrbo logo
View deal
city photo
Chappaquiddick Island

Chappaquiddick Island travel guide

Let us help you plan your perfect Chappaquiddick Island vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Chappaquiddick Island, and more.

Frequently asked questions

What do I need to know before visiting Chappaquiddick Island, MA?

Before visiting Chappaquiddick Island, MA, you should know that:

  • It is accessible via a bridge from Edgartown.
  • It's a popular area for fishing and boating.
  • It is home to a few beaches, trails, and other outdoor attractions.

In order to fully enjoy the island, it is recommended that you bring the necessary items for a day trip such as a bathing suit, sunscreen, and insect repellent.

What are the must-visit tourist attractions in Chappaquiddick Island, MA?

Chappaquiddick Island, MA is a beautiful destination for tourists, offering a variety of attractions to explore and enjoy. Here are some of the must-visit spots on the island:

  • Mytoi Japanese Garden
  • Edgartown Lighthouse
  • Chappaquiddick Beach
  • Chappaquiddick Community Center

Whether you’re looking for a relaxing day on the beach or a historical tour, Chappaquiddick Island, MA has something for everyone. Make sure to check out these amazing attractions while you’re there!

How can I get around in Chappaquiddick Island, MA?

You can get around Chappaquiddick Island, MA in a few different ways:

  • By car
  • By bike
  • By foot

The island is small enough that all three of these methods are viable and enjoyable options for exploring the island.

Where can I find affordable accommodation in Chappaquiddick Island, MA?

Chappaquiddick Island, MA offers a variety of affordable accommodation options for visitors. Here are just a few of the best:

  • The Chappy Inn: This quaint hotel offers comfortable rooms at unbeatable prices.
  • The Beach House: This charming beachfront cottage is perfect for a romantic getaway.
  • The Inn at Chappaquiddick: Enjoy stunning views and luxurious amenities at this luxurious inn.
  • The Chappy Lodge: This family-friendly lodge offers a variety of activities for all ages.

No matter your budget, Chappaquiddick Island, MA has something for everyone!

What is the culture like in Chappaquiddick Island, MA?

Chappaquiddick Island, MA is a small island located off the coast of Martha's Vineyard. It is known for its laid back atmosphere and strong sense of community. Here are five key aspects of the culture on Chappaquiddick Island:

  • Family-oriented: Residents of Chappaquiddick Island are very close-knit, and family is highly valued. Many families have lived on the island for generations.
  • Outdoor activities: The island is home to many outdoor activities such as fishing, boating, and swimming. There are also several nature trails for hiking and biking.
  • Historic sites: Chappaquiddick Island is home to several historic sites, including the Kennedy Compound and the Mytoi Japanese Garden.
  • Arts and culture: The island is home to several art galleries and museums, as well as a thriving music and theater scene.
  • Local cuisine: The island is home to many restaurants serving up fresh seafood and other local delicacies.

Is Chappaquiddick Island, MA safe to travel to?

Chappaquiddick Island, MA is generally considered safe to travel to. Here are some tips for staying safe while in the area:

  • Avoid travelling alone at night.
  • Be aware of your surroundings.
  • Familiarize yourself with the island before visiting.

What are the popular shopping destinations in Chappaquiddick Island, MA?

Chappaquiddick Island, MA is a popular destination for shopping. Here are some of the highlights:

  • The Chappaquiddick Island General Store, which offers a variety of unique items and souvenirs.
  • The Chappaquiddick Island Trading Post, which offers a wide selection of clothing, jewelry, and other items.
  • The Chappaquiddick Island Crafts Fair, which sells handmade items from local artisans.

What are the best neighborhoods to visit in Chappaquiddick Island, MA?

The best neighborhoods to visit in Chappaquiddick Island, MA are:

  • Katama Bay
  • Chappaquiddick Beach
  • Mytoi Gardens

Katama Bay is a great spot for swimming, fishing, and boating. Chappaquiddick Beach is a beautiful beach with white sand and crystal clear water. Mytoi Gardens is a peaceful spot with Japanese-style gardens and paths.

Where is Chappaquiddick Island, MA?

Chappaquiddick Island, MA is an island off the coast of Massachusetts. It is part of the town of Edgartown, and is connected to the mainland via a small bridge. It is a popular tourist destination due to its beautiful beaches and rich history.

What are the most popular vacation rental amenities in Chappaquiddick Island, MA?

The most popular vacation rental amenities in Chappaquiddick Island, MA include:

  • Spacious outdoor areas
  • Fully-equipped kitchen
  • High-speed internet access
  • Air-conditioning
  • Flat-screen TVs

Additional popular amenities include a private pool, hot tub, fire pit, and outdoor furniture. Many vacation rental properties also offer amenities such as a washer and dryer, beach access, and a private dock.

What are the top things to do in Chappaquiddick Island, MA?

Chappaquiddick Island, MA is a great place to visit for a variety of activities. Here are some of the top things to do:

  • Take a scenic walk along the Chappaquiddick Beach
  • Explore the Mytoi Japanese Garden
  • Visit the Edgartown Lighthouse
  • Go fishing or kayaking in the Chappaquiddick Harbor

No matter what you choose to do, Chappaquiddick Island, MA is sure to provide a great experience.

What is the price range for rentals in Chappaquiddick Island?

Vacation rentals in Chappaquiddick Island have a price range between $247-$10,000. The average price for rentals in Chappaquiddick Island is $635 per night.

What are the most popular vacation rental amenities in Chappaquiddick Island?

  • Internet / Wifi
  • Kitchen / Kitchenette
  • TV

Explore near Chappaquiddick Island

Rentals near top attractions

Related vacation destinations

Nearby vacation destinations

Travel inspiration

Keep exploring