20 Fantastic Martha’s Vineyard Rentals for the Perfect Summer Vacation

Colorful houses Oak Bluffs Marthas Vineyard Massachusetts

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Looking for Martha’s Vineyard rentals for your upcoming vacation? This small island off the southeastern shore of Massachusetts is an incredibly popular summer vacation destination, so you’ll find plenty of options for vacation rentals all across the island.

However, you also want to book yours early — as a popular destination, the best places book up very quickly!

Before you book, check out our guide to the Martha’s Vineyard towns to get the lay of the land.

If you prefer a little more pampering, check out our guide to a variety of Martha’s Vineyard hotels instead.

If you’re bringing your fur-baby, here are the best pet-friendly hotels and rentals on Martha’s Vineyard.

The Top Martha’s Vineyard Vacation Rentals

Vacation Rentals in Aquinnah

Beachroad Hideout

The Beachroad Hideout is one of the few Martha’s Vineyard vacation rentals in Aquinnah on the western side of the Vineyard.

The home is great to rent for families or friends since it has three bedrooms, a full kitchen, and plenty of living space. 

It also comes with a fire pit, a grill, a sunroom, and a large living room with plenty of seating for spending quality time with friends and family. 

And, when you’re ready to get out and explore the island, the beach is a quick walk away.

There are beach towels at the house for guest use as well.

Aquinnah Cliffs and Gay Head Light in Aquinnah Marthas Vineyard Massachusetts

Chilmark Vacation Rentals

Peaceful Chilmark Farmhouse by Menemsha Beach

One of Chilmark’s best MV vacation rentals is the Peaceful Chilmark Farmhouse

The house is great for bigger groups or a multi-family stay, as it has four bedrooms with a combination of twin and queen beds, plus a futon in the sunroom. 

Menemsha is less than a half-mile away from the house, where you’ll find a beach, a harbor, restaurants, shopping, and a fish market. 

This is also one of the best sunset spots on the Vineyard!

When you return to the house after a fun day, there is a TV, a fireplace, books, board games, a deck, a grill, and a fully equipped kitchen for you to enjoy. 

Sunset crowds at Menemsha Beach in Menemsha Chilmark Marthas Vineyard Massachusetts

Chilmark Charm

Chilmark Charm is one of the great homes for rent in Martha’s Vineyard for smaller families. 

The house has two bedrooms and one bathroom, plus a full kitchen and an outside deck perfect for enjoying the summer weather.

Even though it has fewer bedrooms, the house has an open layout and a lot of natural light, so the inside is great for spending time together and truly relaxing. 

From the house, it’s easy to get to both beaches and hiking trails. 

The Bird’s Nest

The Bird’s Nest is another great option for vacation rentals in Chilmark. 

The best part of the house is the partial ocean views it offers.

Since you are close to the water and the beach, it is the perfect place to stay if you want to boat, swim, or watch the sunset over the water. 

Inside, the home is cozy with a skylight, a screened-in porch, and a grill, so you have everything you need for a comfortable, enjoyable stay.

Hillside Oak

Hillside Oak is one of the best Martha’s Vineyard house rentals if you want to spend some time on the island hiking. 

While the beaches are the obvious draw, the Vineyard also offers outdoor enthusiasts plenty of other fun things to do!

The house itself is actually situated in the forest, and you are only a few minutes away from plenty of hiking trails and paths. 

There is also a private beach 10 minutes walking distance from the house, and you can see the ocean from the house. 

It’s the perfect combination!

The house is quite open, so you can enjoy the forest views even when you are inside, and the house is equipped with everything you need for a great stay. 

Menemsha Beach sunset in Menemsha Chilmark Marthas Vineyard Massachusetts

Edgartown Vacation Rental Options 

Wooded Oasis

Wooded Oasis is one of the most peaceful and simple rentals on Martha’s Vineyard, perfect for larger families since it has three bedrooms. 

The house is in the woods, so it is good for a quiet getaway, but you are still near beaches, a wildlife sanctuary, golfing, and hiking. 

There is also a deck so you can enjoy your time at the rental surrounded by nature and wildlife. 

Harbor Cove Cottage 

Harbor Cove Cottage in Edgartown is one of the cutest Martha’s Vineyard cottage rentals. 

The cottage is in the perfect location, right by the beaches, as well as golf courses and plenty of restaurants. 

And families will love it since it has a lot of space to spend time together, plus a playground for the kids and a deck with a grill for easy dinners at home together.

The Entering Edgartown sign Marthas Vineyard Massachusetts

Pretty on Prada

Pretty on Prada is another one of Edgartown’s lovely houses for rent. 

You have a lot of privacy in this four-bedroom home, but you are also close to the town, the beach, and bike paths. 

There is a grill for guest use outside on the deck.

Alternatively, head to town where there are plenty of restaurants to choose from. 

Charming Martha’s Vineyard Home

This Charming Martha’s Vineyard Home is in the perfect location no matter what you want to do on the island. 

There are two bedrooms in the house plus additional sleeping space for up to 6 adults to stay.

You’ll also enjoy a large, airy living area and a large deck outside for gathering together indoors or out. 

When you’re ready to get out and explore, you have access to the Pennywise Trail from the backyard as well as proximity to multiple beaches, bike rentals, and wildlife areas. 

A view of Edgartown Harbor Lighthouse in Edgartown Marthas Vineyard Massachusetts

Rentals in Oak Bluffs

Oak Bluff Bungalow Bliss

One of the best-rated rentals on Martha’s Vineyard is the Oak Bluff Bungalow

The house is one of the biggest available, with five bedrooms, three and a half bathrooms, a large living and dining area, a patio, a large porch, and a children’s play area outside. 

Beyond just being able to house a larger group, this home boasts lots of other great bonus options!

Don’t worry about bad weather, you can all gather inside at the house’s indoor movie theater.

Or spend your evenings playing in the game room with a pool table and darts.

You’ll all love spending time together in this spacious home creating special memories.

Farmhouse Fantasy

Another one of the popular Martha’s Vineyard houses to rent in Oak Bluffs is Farmhouse Fantasy

There are three beaches just over a mile away, and the house has a great yard and deck for hanging outside. 

The home has three bedrooms, a bright living space, and an open floor plan with plenty of space for your family and friends!

With its 19-century farmhouse charm plus such easy access to the island fun on the Vineyard, this home offers an idyllic stay.

Marthas Vineyard Sandbar outdoor dining Oak Bluffs Marthas Vineyard Massachusetts

Island Inn Condominiums

Island Inn Condominiums (30 Island Inn Road, Oak Bluffs) offers a resort-style stay in vacation condos.

Complete with luxury amenities, such as an outdoor swimming pool with sun loungers, an outdoor terrace to enjoy, and fully-equipped apartments to stay in, the Island Inn is a great place to stay.

Each vacation unit is outfitted with a full kitchen, flat-screen satellite TV, full living room area, and private bathroom.

You can also find a washing machine, dining area, and seating area in each apartment.

The modern suites are decorated in muted coastal tones which makes for a stylish and comfortable stay.

The Island Inn Oak Bluffs offers a premium stay with great amenities for those looking to visit for a couple of days or for an extended period on Martha’s Vineyard.

Colorful houses Oak Bluffs Marthas Vineyard Massachusetts

Martha’s Vineyard Apt Near Inkwell Beach

For something smaller than a rental home but still in a great location, check out this Martha’s Vineyard Apartment.

There are two bedrooms in the apartment, plus more sleeping space in the living areas for up to 6 adults to stay. 

The apartment is close to beaches, particularly popular Inkwell Beach, as well as all the attractions and restaurants in Oak Bluffs. 

Even though it is smaller than a vacation home, the apartment has ample space for a family.  

White Pearl

The last vacation home in Oak Bluff that we highly recommend is the White Pearl

The three-level, three-bedroom home is full of beautiful white furniture and decor, making it great for an adults-only trip to Martha’s Vineyard. 

The house is in a quiet neighborhood, and you have a firepit and a furnished deck with a grill to enjoy dining al fresco together in the evenings. 

There is plenty of living space inside the home, including a nice kitchen and dining room, plus fast internet to back up all your beautiful beach photos each day. 

You can easily get to beaches, golf courses, and nature areas from the house. 

Plus, there are beach chairs at the home you can use during your stay!

Entering Oak Bluffs sign Marthas Vineyard Massachusetts

Vineyard Haven/Tisbury Rentals

Vineyard Escape

Thanks to its location, Vineyard Escape is one of the best houses for rent in Martha’s Vineyard in Vineyard Haven. 

The house is close to the water, where you can enjoy water activities like fishing, kayaking, surfing, and more. 

Also nearby is a golf course.

The home is convenient to the center of Vineyard Haven, which is full of shops, restaurants, and entertainment. 

Be sure to visit the Martha’s Vineyard Museum (151 Lagoon Pond Rd) to learn local history while you’re here!

Marthas Vineyard Museum and sign in Vineyard Haven Marthas Vineyard Massachusetts

Island Home

If you are looking at smaller vacation rentals on Martha’s Vineyard, you should consider this Island Home.

It has two bedrooms and is really cute with a fireplace, a farmhouse vibe, and a lot of bright light. 

There’s also a nice outdoor deck at the back of the house for outdoor space.

You can walk to the beach as well as town from this home, making for easy exploring and relaxing during your vacation.

North Bluff Bungalow 

North Bluff Bungalow is one of the highest-rated Martha’s Vineyard vacation rentals. 

The house is perfect for stays with kids since there are four bedrooms, a play area, a large backyard, and plenty of indoor space. 

Near the home is the beach and a playhouse, which both kids and adults will love! 

The East Chop Lighthouse and Telegraph Hill sign Vineyard Haven Marthas Vineyard Massachusetts

West Tisbury Vacation Rental Homes

Lambert’s Cove Estate

One of the largest houses in Martha’s Vineyard is Lambert’s Cove Estate, which has four bedrooms and many indoor and outdoor living spaces. 

At the house, you can enjoy beautiful views from one of two porches, a large yard, an outdoor grill, and a lot of natural light. 

And, you are less than a mile away from the beach!

Spend your day in the sea and sand, and then rinse off with an outdoor shower back at the house.

Island Forest Retreat 

Another one of West Tisbury’s nice Martha’s Vineyard rentals is the Island Forest Retreat, which has four bedrooms and two and a half bathrooms.

The home has a cozy vibe with a fireplace, wooden panel walls, and a comfy living space. 

It’s a great place to stay in the summer since it has a large deck with a grill, and it is convenient to all the island fun, including a bike path, a beach, and mini-golf.

You can also easily reach Edgartown, Vineyard Haven, and Oak Bluffs from here with your own car. 

Oyster Pond Paradise 

Our final recommended Martha’s Vineyard vacation rental is Oyster Pond Paradise.

The home is one of the larger ones, with five bedrooms and three and a half bathrooms accommodating up to 13 people.

Two of the home’s main attractions are the rooftop deck and the private hot tub, which people of all ages will enjoy. 

The home’s location is great since you are by the beach, as well as trails for hiking and biking, and a forest. 

Inside the home is a large living room with a sleeper sofa, a full kitchen, and a large dining area that will fit your whole family or all your friends. 

Front of Alleys General Store in West Tisbury Marthas Vineyard Massachusetts

Final Words

We hope this list of Martha’s Vineyard vacation rentals has helped you plan your summer getaway! Let us know if we missed your favorite spot in the comments below.

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