Discover a selection of 1,000 vacation rentals in Chappaquiddick Island, Edgartown 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 $227 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
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.

What are the top vacation rentals in Chappaquiddick Island?

From high-end condos to inexpensive cottages, Vrbo has properties to fit all budgets and tastes. Here are some of the top vacation rentals in Chappaquiddick Island:

  • "Private Chappy House - Walk To Beach": If you're looking for a comfy space in Edgartown, this rental won't disappoint. It comes with 3 bedrooms and amenities like an oven and an iron and ironing board.
  • "3 Bedroom Chappy Cottage, Newly Renovated": Book a few nights or more at this escape in Edgartown and you'll have access to an electric kettle, a separate dining area and more. It has 3 bedrooms to accommodate your family and friends.

For even more great options, use the search bar at the top of the page to find the perfect Chappaquiddick Island vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in Chappaquiddick Island?

If you need an escape and a change of scenery, we've got the answer. Return home feeling like a new person after a weekend getaway in Chappaquiddick Island at one of these top-rated rentals:

  • "Chappy Cottage": Two or three days away at this Edgartown stay will have you feeling fresh as a daisy. Convenient amenities here include a garden and outdoor furniture. When it's time to go exploring, Englewood Beach and Ropes Beach are among the natural attractions in the area.
  • "Private Beach House. Now Available Late August": With conveniences including games and a kitchen, you're guaranteed to feel right at home at this Edgartown getaway. Outdoorsy travelers will love checking out the local sights, like Bayview Beach and Lambert's Cove Beach.

Can I find studio apartments for rent in Chappaquiddick Island?

Usually conveniently located and at a price that won't break the bank, studio apartments offer style and privacy with the comforts of home. Book one of these studio apartments for rent in Chappaquiddick Island and use it as a base to explore what's around you:

  • "1 Bedroom Condo With A Balcony And Covered Parking Less Than Two Blocks From The Slopes" in Edgartown puts you within close reach of some of the area's top cultural attractions, including Harwood Museum of Art and Henningsen Fine Arts. High-speed internet services and an oven are a couple of the amenities you'll have at hand here.
  • Located in Postira, "Apartment Puli - 200m From Sea: Nela1 - 2" is another terrific base for your adventure. When you're not out exploring highlights like Archaeological Museum and Jaman Gallery, make use of a garden and an iron and ironing board back at your apartment.

Can I find short term rentals in Chappaquiddick Island?

Yes, so forget about holing up in a lifeless hotel or paying to sleep in someone's spare room. Select one of our short-term rentals in Chappaquiddick Island and live large in your own private hideaway. Here are two options we think you'll love:

  • You'll be close to central Edgartown when you stay at "Chappy Cottage". Make the most of your whirlwind adventure by exploring the nearby sights, starting with Edgartown Lighthouse and South Beach.
  • Experience the best Edgartown has to offer from "Private Beach House. Now Available Late August". If you book this vacation rental, Edgartown Lighthouse and Lighthouse Beach are some highlights to put on your itinerary.

What are the best romantic weekend getaways in Chappaquiddick Island?

Whether you've been together for a couple of months, a year or an eternity, nothing beats a romantic weekend getaway to keep the flames of love burning. If you're after someplace idyllic to spend a few days with your boo, you'll fall hard for these retreats:

  • "Private Chappy House - Walk To Beach" in Edgartown sets the scene for romantic interludes. It's full of nice touches, including a nearby bay and winery tours.
  • Alternatively, spend a few days sipping Champagne and cuddling up at "3 Bedroom Chappy Cottage, Newly Renovated". A nearby bay and a dining table add to the atmosphere of this property in Edgartown.

What are the best large group vacation rentals in Chappaquiddick Island?

When it comes to who you go on vacation with, the more people the merrier. If you're searching for a property with ample space to fit the entire family, one of these large group vacation rentals in Chappaquiddick Island could be your perfect pad:

  • "Secluded Chappy 2023 Peak Season Weeks Available": Featuring 5 bedrooms, this popular option in Edgartown has more than enough room for you and the whole gang. Amenities like a kitchen and a garden will keep everyone happy.
  • "Gracious Victorian On Chappy": Located in Edgartown, this roomy option has 7 bedrooms and is another favorite for a big family get-together. There's plenty to keep guests both comfortable and entertained, such as a garden and a fireplace.

What are the best houses for rent with a pool in Chappaquiddick Island?

Take your pick and cannonball right in. Here are a couple of top-rated house rentals in Chappaquiddick Island where happiness is a day at the pool:

  • Parents, kids, uncles, aunts — everyone will love relaxing by the pool at "Private Chappy House - Walk To Beach". Treat the whole family on a trip to this Edgartown rental house which also features childrens activities and a travel crib.
  • "Private Beach House. Now Available Late August" in Edgartown is also popular with guests. There's so much to love about this place apart from its pool, such as beach sun loungers and outdoor furniture.

What are the best large family vacation rentals in Chappaquiddick Island?

Start sending out those invites, because Vrbo has lots of family vacation rentals in Chappaquiddick Island that'll put out the welcome mat for your gang. Try these on for size:

  • "Private Chappy House - Walk To Beach" in Edgartown will make your family trip a memorable one. It has 3 bedrooms sleeping up to 8 guests and a range of amenities, including nearby birdwatching activities and a dishwasher.
  • Alternatively, book your family trip at "Private Beach House. Now Available Late August". This Edgartown property has 5 bedrooms and can accommodate up to 9 people. Take advantage of beach sun loungers and a fridge during your stay.

Are there one-bedroom vacation rentals in Chappaquiddick Island?

From cozy B&Bs to sprawling houses and everything in between, we've got properties in all sizes and shapes. If you don't need a lot of space, one of our one-bedroom vacation rentals will be just the thing:

  • Spend a few nights or more at "Elegant Designer Cottage In Edgartown" and discover why this one-bedroom rental in Katama is a favorite with many visitors. A kitchen and a garden are just a couple of the conveniences that help make this stay a standout.
  • Or, put your bags down and make yourself comfortable at "New Build | Private Locale On 16 Acres | Central Ac And Outdoor Shower". An electric car charging station and a kitchen are just two of the amenities that are available at this option in City Centre Regensburg.

Can I find two-bedroom vacation rentals in Chappaquiddick Island?

From rustic cabins to ritzy houseboats, Vrbo has two-bedroom vacation rentals to suit all budgets and styles. Here are a couple of our top picks in Chappaquiddick Island:

  • Invite some of your friends to share in the good times at "Chappy Cottage". As well as two bedrooms, this Edgartown retreat has everything you need for a relaxing stay, including a garden and a fireplace.
  • Or, create unforgettable memories with your favorite people at "Chappaquiddick - Hidden Gem On Chappy". This popular option in Edgartown comes with a kitchen and a garden.