10 Best Vacasa Rentals In Martha's Vineyard, Massachusetts - Updated 2024

Sowmya
Sowmya  
Updated
| 6 min read

A beloved summer destination, Martha’s Vineyard is an island set off Cape Cod in Massachusetts. Visitors flock here to enjoy its laidback charm and gorgeous beaches. The island has six charming towns—Edgartown, Tisbury, West Tisbury, Oak Bluffs, Aquinnah and Chilmark. While beaches remain a top draw, there are several other interesting places to explore across these towns. For nature lovers, the stunning Aquinnah Cliffs and Felix Neck Wildlife Sanctuary are excellent options. Edgartown Harbor Light, Jaws Bridge and Gingerbread Houses are some of the must-visit landmarks in Martha’s Vineyard. Planning a vacation to this delightful destination and wondering where to stay? Our curated list of the best Vacasa rentals in Martha’s Vineyard, Massachusetts, will help you shortlist superb options, so read on.

We handpicked these listings carefully, considering (wherever possible) Superhost status. recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on February 09, 2024.

1. Hillside Oak (from USD 427)

Situated on the outskirts of Menemsha, this house offers a cosy vibe with warm home-like furnishings and vintage touches, such as a stone fireplace, beamed ceilings and hardwood flooring. The house is surrounded by woods, so you will be enveloped by greenery all around.

The two-story house offers a brightly lit open-concept living space that combines a lounge space and dining space, warmed by a wood stove. A small but fully stocked kitchen comes separately. Head to the family room for relaxed evenings. Entertainment options include books from the home library and board games.

A deck set up with a barbecue grill and patio furniture offers space for refreshing outdoor time. Washing equipment and WiFi are other facilities available. Please note that the property does not provide any air conditioning.

Stayed at this property?
Chilmark, MA
6 reviews  
8 Guests 4 Bedrooms 4 Bathrooms

2. Spacious estate with a hot tub (from USD 750)

You are sure to love the elegant ambience of this large property and the upscale facilities it offers. Located conveniently just 4 mi (6.4 km) from Long Point Beach, this rental is spread over three floors and has contemporary-style interiors.

High-beamed ceilings and large windows characterize its open-plan main living space, which includes a gourmet kitchen and a formal dining space. Adjoining is a screened-in porch where you can step out for some quiet time. You will find several more spots to enjoy the woodsy setting of this house. Head to the wooden deck set up with a gas grill and garden furniture or the rooftop deck with great countryside views. After a day on the beaches, you can take a dip in the hot tub to soothe those tired muscles.

Stayed at this property?
West Tisbury, MA
13 reviews  
10 Guests 4 Bedrooms 3 Bathrooms

3. Bright cottage with a well-equipped kitchen (from USD 114)

Bright and cheery with coastal-themed decor, this cottage is a delightful rental located right in the middle of Chappaquiddick Island. You will love its lovely interiors that feature quirky touches and colourful furnishings. The common area is warmed by a stove housed inside a stone fireplace and encompasses a seating area and a fully equipped kitchen.

Adjoining the house is a large wooden deck perfect for mellow evenings. This rental is particularly ideal for those looking to go off the grid as it does not offer facilities such as WiFi, air conditioning and televisions.

Stayed at this property?
Edgartown, MA
11 reviews  
4 Guests 4 Bedrooms 1 Bathroom

4. Vineyard Artist's Haven (from USD 394)

Tucked away within woodsy grounds, this two-story rental with sophisticated interiors has a country manor feel.

Spread over two levels, the house is expansive with generous-sized rooms, ensuring both privacy and sufficient common space for gatherings. Pick up a book from the large collection available and relax in the living area or head to the entertainment lounge on the upper level.

A fully equipped kitchen with eat-in facilities comes separately and has everything for those times you want to enjoy freshly cooked meals. Savour the quiet surroundings from the deck, which comes with outdoor furniture and a barbecue grill. Location wise, the property is very convenient as both the harbour and the town centre are a short walk away.

Stayed at this property?
Vineyard Haven, MA
34 reviews  
8 Guests 4 Bedrooms 3 Bathrooms

5. Wayland Victorian (from USD 500)

You will love the graceful vibe of this renovated property, which features a wonderful mix of classic Victorian charm and modern furnishings. The main living space on the ground level is flooded with natural light, making it a welcoming spot to cosy up with a book from the property’s home library or a TV show. Adjoining is a cute window seat that’s another nook ideal for relaxing.

A fully equipped kitchen is also on this floor, featuring all major appliances including a coffee machine and a dishwasher. Wayland Victorian has an advantageous location as both the ferry terminal and downtown Oak Bluffs are around 0.5 mi (0.8 km) away.

Stayed at this property?
Oak Bluffs, MA
8 reviews  
10 Guests 4 Bedrooms 2 Bathrooms

6. Casa de Reyna (from USD 532)

Nestled between pine trees just 1 mi (1.6 km) from Edgartown’s downtown, this three-level rental is a peaceful retreat ideal for large groups or families.

The house’s pleasing interiors feature chic decor and traditional touches, such as hardwood flooring and stonework. With spacious decks on each level, multiple cosy nooks with comfy furniture and a dedicated entertainment room, you will find ample space, whether for unwinding alone or spending quality time with your family or friends. Kids will love the snug attic space in particular, where they can curl up in privacy.

A full kitchen, equipped for all your cooking needs, is available as well, offering essential appliances such as a dishwasher. Outside, you’ll find a well-furnished flagstone patio surrounded by greenery, which comes set up with a fire pit, a gas grill and sufficient seating.

Please note that this house is available only during the summer season.

Stayed at this property?
Edgartown, MA
21 reviews  
8 Guests 3 Bedrooms 3 Bathrooms

7. Katama Woods (from USD 387)

Skylights and tall windows dot this house, giving it a refreshingly open feel. The living area is expansive and features vaulted ceilings and floor-to-ceiling windows. Here, you will find a seating area warmed by a fireplace, a fully equipped kitchen as well as two dining spaces.

This property’s woodsy setting can be best enjoyed from the screened-in covered porch or the adjacent deck. Enjoy al fresco meals and relaxed gatherings at the deck, which has been set up with barbecue equipment and patio furniture. Free WiFi, an outdoor shower, washing equipment and centralised air conditioning are the other useful facilities offered by this rental.

Stayed at this property?
Edgartown, MA
20 reviews  
6 Guests 3 Bedrooms 2 Bathrooms

8. Beautiful home with spectacular ocean views (from USD 248)

Prime location and distinctive architectural styling make this property special. Designed by a notable architect, this iconic house located five minutes from Menemsha beach offers mid-century decor and wooden interiors. Some of its features are the stunning ocean views from several windows, a private swimming pool and an expansive wraparound deck.

Lined with floor-length windows, the open-plan main living area is its heart. You can relax in the seating area with a TV and a fireplace. There’s also a full kitchen with major appliances, including a dishwasher and Nespresso machine. The house offers WiFi, but there’s no air conditioning.

Stayed at this property?
Chilmark, MA
15 reviews  
8 Guests 4 Bedrooms 2 Bathrooms

9. Serene retreat with a wraparound deck (from USD 300)

As you step into the open-plan main living room of this property, you will be struck by its chic mid-century vibe. Featuring a slanted wood ceiling, elegant furniture and floor-length windows, this open layout space encompasses a full kitchen, a dining area as well as a seating area with a fireplace.

The wraparound deck is sure to be your favourite space to hang out. Sit back with your morning coffee here and enjoy the wooded surroundings or go for an al fresco meal as it comes with a gas grill. An outdoor shower, free WiFi, washing equipment and partial air conditioning are other facilities guests enjoy.

Stayed at this property?
Chilmark, MA
8 reviews  
8 Guests 4 Bedrooms 2 Bathrooms

10. Peaceful home with a screened-in porch

Set overlooking the open fields, this rental has a simple home-style ambience that will charm you. Available only in the month of June, this property uniquely offers access to a semi-private dock as a part of the rental fee. Its open-plan living room features a skylight and large windows, making it an inviting space where you can relax after a busy day of sightseeing.

For restful lounging, the screened-in porch provides the best setting. But the rooftop deck is definitely the highlight of the rental. It’s where you can savour the panoramic views of the surrounding fields and even the ocean.

A fully equipped kitchen and WiFi are at your disposal, but no air conditioning is available.

Stayed at this property?
Chilmark, MA
4 reviews  
4 Guests 2 Bedrooms 1 Bathroom

Plan a memorable Martha's Vineyard vacation

A holiday in Martha’s Vineyard is something many of us dream about. With our list of the best Vacasa rentals in Martha’s Vineyard, Massachusetts, you will easily find accommodation options that will make your stay unforgettable.

Stayed at this property?
Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Writing and travelling both bring joy to Sowmya's life. Her favourite destination so far is Bhutan - a land of incredible beauty! And her favourite style of travelling is solo backpacking!...Read more

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