Chappaquiddick Island vacation rentals

We found 946 vacation rentals — enter your dates for availability

Uncover the serene beauty of Chappaquiddick Island, where stunning beaches and historic lighthouses beckon travelers to unwind and explore. This idyllic destination is perfect for group adventures, offering outdoor activities like biking and kayaking in a tranquil setting. Stay in charming cottages or modern condos that provide the comfort and local charm needed for a memorable getaway. With the added convenience of spacious accommodations, you’ll feel right at home while creating lasting memories together.

Holiday rentals with weekly discounts - Chappaquiddick Island

Showing deals for:Dec 18 - Dec 25

Sun room off the kitchen.
Exterior
Outdoor relaxing!
Double sinks for busy kitchens.
Exceptional
(6 reviews)

WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!

Edgartown

9% off
$3,267
$22,868 for 7 nights
All fees included
WALK TO VILLAGE LOCATION, NEW POOL, FAMILY COMPOUND!
Kitchen with panoramic west-facing window
Open concept living space on the second floor with custom octagonal ceiling
Back of house
Outdoor relaxation
Exceptional
(30 reviews)

Luxury Chappaquiddick Getaway with Oceanviews

Edgartown

8% off
$702
$4,914 for 7 nights
All fees included
Luxury Chappaquiddick Getaway with Oceanviews
Living area
Dining
Exterior
Interior
Exceptional
(5 reviews)

Beach Getaway - Spacious Katama Beach House

Edgartown

9% off
$3,346
$23,424 for 7 nights
All fees included
Beach Getaway - Spacious Katama Beach House
Exterior
Living area
Dining
Living area
Exceptional
(17 reviews)

THE PARK ESTATE! Your Martha's Vineyard Getaway!

Oak Bluffs

9% off
$7,335
$51,342 for 7 nights
All fees included
THE PARK ESTATE! Your Martha's Vineyard Getaway!
Interior
Living area
Dining
Private kitchen
Exceptional
(6 reviews)

Spacious home for entertaining, centrally located to beach, ferry, and airport.

Edgartown

9% off
$3,018
$21,127 for 7 nights
All fees included
Spacious home for entertaining, centrally located to beach, ferry, and airport.
Interior
Interior
Private kitchen
Outdoor dining
Exceptional
(51 reviews)

Luxury Loft Historic Center Oak Bluffs

Oak Bluffs

20% off
$592
$4,144 for 7 nights
All fees included
Luxury Loft Historic Center Oak Bluffs
Interior
Terrace/patio
Private kitchen
Exterior
Exceptional
(7 reviews)

BRAND NEW!

Oak Bluffs

9% off
$1,019
$7,135 for 7 nights
All fees included
BRAND NEW!
Your closest neighbors are a family of Osprey!
This unique home was
carefully renovated to maintain its original character.
Laughter and stories are guaranteed as you
get together on the West Porch.
Choose from a variety of seating areas
overlooking the ocean and harbor.
Exceptional
(28 reviews)

Oceanfront, Private Dock and Harthaven Private Beach - Walk to Noman's, Inkwell

Oak Bluffs

9% off
$4,561
$31,925 for 7 nights
All fees included
Oceanfront, Private Dock and Harthaven Private Beach - Walk to Noman's, Inkwell
Private kitchen
Living area
Living area
Property grounds
Excellent
(36 reviews)

A Vineyard Home Perfect For Family Gatherings

Vineyard Haven

8% off
$641
$4,490 for 7 nights
All fees included
A Vineyard Home Perfect For Family Gatherings
Exterior
Terrace/patio
Dining
Living area
Exceptional
(14 reviews)

Charming Katama Home in Prime Edgartown Location!

Edgartown

17% off
$830
$5,808 for 7 nights
All fees included
Charming Katama Home in Prime Edgartown Location!
Kitchen
Front of main house at 47 Cooke St Edgartown MA
Front view of main entrance
Hot tub and heated pool
Exceptional
(56 reviews)

Edgartown close to beach and town 6BD with Pool and Hot Tub

Edgartown

9% off
$2,078
$14,548 for 7 nights
All fees included
Edgartown close to beach and town 6BD with Pool and Hot Tub
Private kitchen
Outdoor dining
Exterior
Living area
Exceptional
(129 reviews)

On HGTV! New w/ Hot Tub, Bocce Court, AC, WALK to Town & Beach!

Edgartown

8% off
$508
$3,556 for 7 nights
All fees included
On HGTV! New w/ Hot Tub, Bocce Court, AC, WALK to Town & Beach!
Living area
Outdoor shower with over-sized rainfall shower head.
Kitchen with new hardwood floors
New chairs for 2023
Exceptional
(95 reviews)

Charming, Clean And Well Maintained Home Walking Distance To Town And Beach

Vineyard Haven

8% off
$435
$3,042 for 7 nights
All fees included
Charming, Clean And Well Maintained Home Walking Distance To Town And Beach
Living room / Dining area
Approach to our home
Kitchen
Loft area
Exceptional
(16 reviews)

Katama Edgartown... bike to South Beach, bike to Town

Edgartown

8% off
$474
$3,318 for 7 nights
All fees included
Katama Edgartown... bike to South Beach, bike to Town
Living area
Outdoor dining
Living area
Exterior
Exceptional
(16 reviews)

Guest House In Edgartown

Edgartown

8% off
$388
$2,718 for 7 nights
All fees included
Guest House In Edgartown
Terrace/patio
Sunroom with games & books & everything fabulous for a long, sweet morning!
Interior
Interior
Exceptional
(38 reviews)

Beautiful Historic Hilltop Haven -Walk to Town & Water

Vineyard Haven

8% off
$486
$3,401 for 7 nights
All fees included
Beautiful Historic Hilltop Haven -Walk to Town & Water
Living area
Outdoor dining
Private kitchen
Exterior
Exceptional
(8 reviews)

Charming 4-bedroom house with AC and WiFi in beautiful Edgartown

Edgartown

9% off
$356
$2,491 for 7 nights
All fees included
Charming 4-bedroom house with AC and WiFi in beautiful Edgartown
Room
Dining
Property grounds
Private kitchen
Exceptional
(9 reviews)

Lovely Home Prvt Apt- 2 bedrms1.5 baths full kitch living /dining rm 2 car prkng

Oak Bluffs

5% off
$414
$2,895 for 7 nights
All fees included
Lovely Home Prvt Apt- 2 bedrms1.5 baths full kitch living /dining rm 2 car prkng
Exterior
Living area
Living area
Private kitchen
Exceptional
(13 reviews)

Chappaquiddick Getaway with stunning Ocean Views, walk to the beach

Edgartown

8% off
$872
$6,103 for 7 nights
All fees included
Chappaquiddick Getaway with stunning Ocean Views, walk to the beach
Room
Dining room
front entrance
Exterior detail
Exceptional
(73 reviews)

Classic Downtown Property

Vineyard Haven

8% off
$523
$3,661 for 7 nights
All fees included
Classic Downtown Property
Dining
Exterior
Living area
Interior
Exceptional
(8 reviews)

Oak Bluffs Retreat! Spacious Vineyard Home Near Beaches & Downtown

Oak Bluffs

8% off
$615
$4,306 for 7 nights
All fees included
Oak Bluffs Retreat! Spacious Vineyard Home Near Beaches & Downtown
Kitchen
House exterior
Bedroom with queen bed
Outdoor shower
Exceptional
(20 reviews)

Charming Family Home in the Heart of Martha's Vineyard

Vineyard Haven

8% off
$597
$4,178 for 7 nights
All fees included
Charming Family Home in the Heart of Martha's Vineyard
Garden Patio
Guest parking for Garden Level unit
Kitchen
Cozy up with a blanket
Exceptional
(43 reviews)

Downtown Oasis, Walk to Beach: Vineyard Vacation Houses Welcomes You!

Oak Bluffs

9% off
$953
$6,669 for 7 nights
All fees included
Downtown Oasis, Walk to Beach: Vineyard Vacation Houses Welcomes You!
Private kitchen
Living area
Living area
Outdoor dining
Exceptional
(31 reviews)

The Seashell Cove - Martha's Vineyard

Edgartown

13% off
$799
$5,595 for 7 nights
All fees included
The Seashell Cove - Martha's Vineyard
  • 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, serene beaches perfect for relaxation and outdoor activities.
  • Historic Lighthouses: Explore iconic lighthouses that offer a glimpse into the island's maritime history.
  • Outdoor Adventures: Enjoy various recreational activities like biking, kayaking, and hiking in a tranquil setting.
  • Charming Accommodations: Stay in cozy cottages or modern condos that provide comfort and local charm.
  • Proximity to Martha's Vineyard: Easily access nearby Martha's Vineyard for additional exploration and cultural experiences.

Popular types of accommodation around Chappaquiddick Island

If you're looking for the perfect getaway on Chappaquiddick Island, you're in the right place. Our most popular accommodations include cozy houses, charming cottages, and modern condos. Whether you seek a peaceful rental cottage or a spacious Chappy rental, we have a variety of options to suit your needs. Discover the beauty and tranquility of Chappaquiddick with our curated selection of vacation rentals today.

  • Houses: The top choice for visitors, these homes offer spacious and comfortable accommodations, ideal for families or groups looking to enjoy a home-like experience.
  • Cottages: Quaint and charming, cottages provide a cozy retreat, perfect for a peaceful getaway by the water.
  • Condos: Offering modern amenities and convenient locations, condos are a great option for those seeking a blend of comfort and accessibility.
  • Apartments: Ideal for solo travelers or couples, apartments offer a homey feel with all the essentials for a pleasant stay.
  • Cabins: Rustic and inviting, cabins allow guests to immerse themselves in nature while enjoying a relaxing vacation.**

Top attractions in and around Chappaquiddick Island

Chappaquiddick Island is a perfect destination for outdoor and beach vacations, offering stunning scenery and cultural experiences. Visitors can explore beautiful beaches, historic lighthouses, and the ferry terminal, making it ideal for adventure seekers. Whether you're interested in Cape Cod vacations or island adventures, Chappaquiddick provides a unique getaway filled with natural beauty and local charm.

  • Chappaquidick Dike Bridge: This monument offers a glimpse into the rich culture of Chappaquiddick Island, serving as a scenic connection between landscapes and a peaceful spot for reflection.
  • Inkwell Beach: A beautiful beach known for its vibrant atmosphere, Inkwell Beach is perfect for sunbathing, swimming, and soaking up the local beach vibes.
  • Oak Bluffs Harbor: Just a short distance away, Oak Bluffs Harbor boasts stunning views, making it an ideal spot for leisurely strolls and enjoying the seaside ambiance.

Things to do recommended for couples

For a romantic getaway on Chappaquiddick Island, indulge in a round at the luxurious Cape Cod Country Club, located 18 miles away. Enjoy stunning views and a serene atmosphere, perfect for couples looking to unwind and reconnect amidst beautiful surroundings.

Things to do recommended for families

Families will love exploring the scenic beaches of Chappaquiddick Island, especially the serene East Beach. Kids can enjoy biking along the island’s trails, while the iconic Dike Bridge offers great views and photo opportunities. Don’t miss the opportunity to spot local wildlife during your visit.

Things to do recommended for groups

Explore the stunning landscapes of Chappaquiddick Island by biking along scenic trails, or gather your group for a fun day of beachcombing at Wasque Beach. Don't miss a visit to the historic Dyke Bridge for breathtaking views and great photo opportunities.

*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

When planning your trip, whether you're traveling with a group, family, pets, or seeking longer accommodations, be sure to use the appropriate filters to meet your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chappaquiddick Island with a group: Think about how many bedrooms you'll require and any additional features like a full kitchen or outdoor area for group gatherings. Luckily, Vrbo allows you to filter for these options and much more.
  • Traveling to Chappaquiddick Island with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chappaquiddick Island: For many families, a vacation isn't truly satisfying unless their furry companion is along for the ride. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chappaquiddick Island: If you're seeking vacation rentals with 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. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Chappaquiddick Island

Chappaquiddick Island offers a serene retreat for those seeking a peaceful beach vacation. With its stunning natural scenery and relaxed atmosphere, visitors can explore picturesque beaches and enjoy outdoor excursions. Nearby Martha's Vineyard enhances the experience with charming neighborhoods and friendly locals. Whether you're looking for quiet relaxation or recreational activities, Chappaquiddick is the perfect destination for an unforgettable island getaway.

  • Martha's Vineyard: This picturesque island, located approximately 9 miles from Chappaquiddick Island, is renowned for its stunning beaches, lush landscapes, and vibrant outdoor activities. Visitors flock to Martha's Vineyard to experience its charming towns, scenic bike paths, and beautiful coastline. Popular attractions include live music concerts, luxurious resorts, and world-class golf courses. With its family-friendly beaches and captivating views of the Cape, Martha's Vineyard is a perfect destination for relaxation and exploration.
  • Edgartown: As the city where Chappaquiddick Island is situated, Edgartown offers a rich blend of history and modern amenities. Known for its stunning beaches and outdoor activities, Edgartown is a haven for beachgoers and nature lovers alike. Visitors can enjoy shopping in quaint boutiques, exploring local galleries, and playing golf at scenic courses. The area's charming streets are lined with beautifully preserved historic homes, making it a delightful place to wander and soak in the scenery.
  • Oak Bluffs: Located around 7 miles from Chappaquiddick Island, Oak Bluffs is a lively city known for its colorful gingerbread cottages and vibrant marina. This family-friendly destination is perfect for those seeking outdoor adventures, with access to beautiful beaches and water sports. Visitors can enjoy shopping at local stores, engaging in educational experiences, or hitting the links at nearby golf courses. The charming atmosphere, along with its stunning coastal views, makes Oak Bluffs a must-visit spot on your vacation.

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 simple

Are you hoping to save on your upcoming trip? Consider being flexible with your travel dates, as this can often lead to better prices. Additionally, booking a longer stay can result in substantial savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board feature is designed to enhance your travel planning experience. It provides you with a dedicated area to start new trips, pick up right where you left off, or organize your existing plans. You can easily access the properties you've saved or booked, now categorized under Potential, Upcoming, or Current Trips. To explore 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.

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