Photo by Jason Kennedy

Chappaquiddick Island vacation rentals

We found 894 vacation rentals — enter your dates for availability

Vacation rentals with weekly discounts - Chappaquiddick Island

Showing deals for:May 22 - May 29

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Chappaquiddick Island

Why visit Chappaquiddick Island

  • Stunning Beaches: Chappaquiddick Island boasts beautiful beaches perfect for relaxation and sunbathing, including a unique nudist beach.
  • Historic Lighthouse: Explore the island's historic lighthouse, a charming landmark that adds to the coastal scenery.
  • Outdoor Activities: Enjoy various outdoor adventures, from hiking to kayaking, amidst the island's lush landscapes.
  • Charming Accommodations: Stay in cozy cottages or stylish condos, offering a comfortable retreat after a day of exploration.
  • Close to Oak Bluffs: Experience the vibrant atmosphere of nearby Oak Bluffs, enhancing your vacation with its friendly locals.

Popular types of accommodation around Chappaquiddick Island

Discover the charm of Chappaquiddick Island with our diverse vacation rental options. Whether you're seeking a cozy cottage, a spacious private vacation home, or a stylish condo, we have the perfect accommodation to suit your needs. With a variety of Chappaquiddick homes for rent, you can enjoy the beauty of Martha's Vineyard while relaxing in comfort. Start planning your getaway today and experience all that Chappaquiddick has to offer.

  • Houses: The top choice for visitors to Chappaquiddick Island, these homes offer spacious accommodations ideal for families, friends, or couples seeking comfort and privacy.
  • Cottages: A delightful second option, cottages provide a cozy, charming atmosphere perfect for a relaxing getaway.
  • Condos: The third most popular choice, condos offer modern amenities and are often located near local attractions.
  • Apartments: A practical fourth option, apartments provide convenient living spaces for travelers looking to enjoy their stay.
  • Cabins: Rounding out the list, cabins offer a rustic and tranquil retreat for those wanting to immerse themselves in nature.**

Top attractions near Chappaquiddick Island

Chappaquiddick Island is a picturesque destination perfect for outdoor enthusiasts and beach lovers. Visitors can explore its beautiful beaches, historic lighthouse, and even a nudist beach. Ideal for those seeking culture and adventure, the island offers a variety of attractions and activities, including stunning coastal scenery. Don't miss the chance to relax and enjoy the unique charm of Chappaquiddick's beaches during your vacation.

  • Inkwell Beach: A picturesque beach known for its vibrant atmosphere, Inkwell Beach is perfect for sunbathing and swimming. Enjoy the soft sands and gentle waves while soaking in the laid-back beach vibes just 7 miles from Chappaquiddick Island.
  • Edgartown Lighthouse: This historic lighthouse, located 2 miles away, offers a glimpse into the maritime heritage of the area. Explore the surrounding scenic views and learn about its rich history, all while enjoying the cultural vibes it radiates.
  • Martha's Vineyard Museum: Situated 8 miles from Chappaquiddick Island, this museum showcases the island's fascinating history and cultural heritage. Visitors can explore engaging exhibits and unique artifacts, making it a must-visit for history enthusiasts.

Things to do recommended for couples

For a romantic getaway on Chappaquiddick Island, try your hand at Island Cove Adventures for some fun mini golf, just 9 miles away. For a touch of luxury, head to Cape Cod Country Club, located 18 miles away, where you can relax and enjoy the beautiful surroundings.

Things to do recommended for families

Families will love the Flying Horses Carousel, just 7 miles away, with its charming outdoor atmosphere. For relaxation, visit Fulling Mill Brook Preserve and Mashpee River Reservation, located 12 and 18 miles away, respectively, both offering serene settings for wellness and family enjoyment.

Things to do recommended for groups

Experience the charm of Martha's Vineyard Film Center for a movie night with family vibes, enjoy a round of golf at Farm Neck Golf Club surrounded by nature, or shop and dine at Mashpee Commons for a lively group outing, all within a short drive from Chappaquiddick Island.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Chappaquiddick Island

If you're planning a trip with a group, traveling with family, bringing your pets along, or seeking extended stays, it's important to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Chappaquiddick Island with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group get-togethers. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Chappaquiddick Island with young kids: Traveling with young kids can present some challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering how close you are to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Chappaquiddick Island: For many families, a vacation wouldn't be the same without their furry companion. If that resonates with you, take a look at Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Chappaquiddick Island: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Be sure to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Chappaquiddick Island

Chappaquiddick Island offers a unique coastal getaway where natural beauty meets charming accommodations like cozy cottages. Explore the picturesque scenery and enjoy outdoor activities, making it a perfect destination for relaxation and recreation. Nearby Oak Bluffs adds to the experience with its vibrant atmosphere and friendly locals, inviting travelers to embark on memorable excursions. Discover the tranquil beaches and lush landscapes that make Chappaquiddick a must-visit spot in Massachusetts.

  • Martha's Vineyard: This picturesque island, located 9 miles from Chappaquiddick Island, is a haven for nature lovers and beach enthusiasts. Famous for its stunning outdoor scenery, Martha's Vineyard offers a range of experiences from relaxing on beautiful beaches to exploring the tranquil lakes. Visitors can enjoy vibrant music concerts and stay at luxurious resorts, or hit the greens at one of the island's acclaimed golf courses. The local attractions, including family-friendly beaches and scenic spots, make it an ideal getaway for families and couples alike.
  • Edgartown: As the city that encompasses Chappaquiddick Island, Edgartown offers a unique blend of charm and coastal beauty. Travelers are drawn here for its outdoor activities and breathtaking beach vistas. Golf enthusiasts can find several impressive golf courses and private country clubs to indulge in their favorite sport. The area is known for its family-friendly beaches and serene lakes, perfect for a relaxing day by the water. Edgartown's quaint streets are also lined with lovely shops and eateries, enhancing its allure for visitors.
  • Oak Bluffs: Located 7 miles from Chappaquiddick Island, Oak Bluffs is a vibrant city known for its lively beach scene and scenic landscapes. The area is popular for its bustling shopping areas and outdoor recreational options, making it an ideal spot for family fun. Golf courses abound for those looking to play a round, while the nearby marina offers opportunities for boating and fishing. With picturesque beaches and family-friendly attractions, Oak Bluffs is perfect for a day of exploration and relaxation under the sun.

Best time to go to Chappaquiddick Island

If you're planning a trip to Chappaquiddick Island, Edgartown, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from June to August, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.2°F (1.8°C)Light RainMostly SunnyLowModerately Low
February35.2°F (1.8°C)Light RainMostly SunnyLowModerately Low
March38.8°F (3.8°C)Light RainMostly SunnyLowModerately Low
April46.4°F (8.0°C)Light RainMostly SunnyAverageAverage
May54.5°F (12.5°C)Light RainMostly SunnyAverageAverage
June63.1°F (17.3°C)Light RainMostly SunnyHighModerately High
July71.1°F (21.7°C)Light RainMostly SunnyHighModerately High
August71.8°F (22.1°C)Light RainMostly SunnyHighModerately High
September66.7°F (19.3°C)Light RainMostly SunnyAverageAverage
October58.6°F (14.8°C)Light RainMostly SunnyAverageAverage
November49.1°F (9.5°C)Light RainMostly SunnyAverageAverage
December41.5°F (5.3°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often result in significant savings. To help you find the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

Plan your group getaway by booking an eligible Vrbo and earn OneKeyCash on your reservation. Being the organizer has its perks. When you join our travel rewards program, One Key, you'll gain immediate access to member discounts and the ability to earn and redeem OneKeyCash on qualifying bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly platform for planning your travels, allowing you to create new trips, continue from where you left off, and manage your itineraries with ease. You can easily find your saved or booked properties organized into categories such as Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Explore the waterfront setting in Chappaquiddick Island

Enjoy the monuments and other features of Chappaquiddick Island. Renowned for its island views, beaches and parks, this city welcomes all visitors. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

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 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.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Chappaquiddick Island?
According to our data, cottages are the most sought-after type of property in Chappaquiddick Island. But as you'd expect, everyone's idea of the perfect stay differs. Vrbo has vacation rentals in a variety of sizes and shapes, and we'll help you locate the perfect match.
How much does it cost to rent a vacation rental in Chappaquiddick Island?
Property type, length of stay and season are among the factors that can determine the price of a vacation home. Simply enter your dates of travel to find your perfect fit. From cozy chalets to plush villas, all Vrbo vacation rentals provide amazing value.
How much does it cost to rent a beach house in Chappaquiddick Island?
When you travel and the size and style of the property will help determine the cost of your beachside stay. Type in your Chappaquiddick Island travel dates to see your options on Vrbo. Did someone just say "hot tub"? Use the filters to select the features and amenities you need.
What are popular rental amenities in Chappaquiddick Island?
When it comes to rental amenities that people look for in Chappaquiddick Island, a swimming pool, a fireplace and a garden are at the top of the list. With Vrbo vacation homes, you'll discover options to match your taste and style, whether you're going on a trip with friends, relatives or even pets.
Can I find two-bedroom vacation rentals in Chappaquiddick Island?
Chappaquiddick Island has nine two-bedroom vacation properties that you can choose from. Go for a vacation home with all the privacy and space you need at a price that won't break the bank on Vrbo.
Are there vacation rentals with WiFi in Chappaquiddick Island?
You can pick from 16 vacation rentals with WiFi in Chappaquiddick Island. If you want to disconnect from daily life while on vacation, but still want to be connected to the web, these getaways are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How old do you have to be to rent a vacation rental in Chappaquiddick Island?
The minimum required age is generally 16, 18 or 21. It can differ from property to property on Vrbo, so look at the rules of your chosen Chappaquiddick Island vacation rental before booking.
How long can I rent a vacation rental in Chappaquiddick Island for?
The length of time you can rent a vacation rental in Chappaquiddick Island is up to the property. Just enter your chosen travel dates to display a list of options offering extended stays. With lots of features such as laundries and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to find someplace just right to call your home away from home in Chappaquiddick Island.
Does Vrbo offer discounts for vacation homes in Chappaquiddick Island?
Whether you've got your eye on one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you're sure to score some fabulous bargains and discounts on Vrbo. From weekend retreats to extended getaways, we've got the ideal place for your next Chappaquiddick Island escape.

More Vacation Ideas