Last Updated October 8, 2021 10/8/2021

Top 16 Martha’s Vineyard Vacation Rentals

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Martha’s Vineyard is one of the most iconic summer destinations on the East Coast and an awesome place to enjoy fresh seafood, lovely beaches, and a laid-back vibe. This is a fun place to explore on a bike and enjoy with someone you love for a little romance or with the kids and dog for a family vacation. To get the most out of the area, there are lots of cottages, guest houses, tiny houses, and other unique rental properties that you can book through Vrbo and Airbnb. Here are some of the best Martha’s Vineyard vacation rentals to look into right now.

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Elegant Farmhouse & Guest House - West Tisbury
Credit: Vrbo.com
All this could be yours on vacation

Elegant Farmhouse & Guest House - West Tisbury

Available to rent on Vrbo, this is one of the most sought-after vacation rentals for large groups up to 10 people in Martha’s Vineyard. It has five bedrooms (four bedrooms in the main house plus a guest house), six beds, and four full baths in a lovely pastoral setting. The home is located on 16 acres and just minutes from Lambert’s Cove Beach. Guests who stay here enjoy the nice decorations inside the home and also the landscaped yard and patio for your outdoor lifestyle in the summertime. Restaurants, farm stands, and West Tisbury Village are all close by when you plan your family reunion or special event here.

Oak Bluffs Gingerbread House with Wraparound Porch - Oak Bluffs
Credit: Vrbo.com
Such a charming entrance when you arrive

Oak Bluffs Gingerbread House with Wraparound Porch - Oak Bluffs

For up to four people, you can rent this adorable vacation rental home with two bedrooms and one bath. It’s an Oak Bluffs home with a charming gingerbread house design and a location that’s within walking distance of Town Beach. Guests also have a fenced backyard, wrap-around porch, and modern kitchen. The Vrbo hosts provide guests with Wi-Fi, beach chairs and toys for the kids, as well as access to street parking when they stay in this two-story rental home.

Adorable Vineyard Haven Cottage - Tisbury
Credit: Airbnb.com
Lovely flowers and a grill in the lawn

Adorable Vineyard Haven Cottage - Tisbury

You can walk to Main Street of Vineyard Haven and the ferry from this comfortable cottage that sleeps up to three people. It’s an Airbnb rental with a screened porch, kitchen, air conditioning, cable, grill, and outdoor shower. The home is also in walking distance from fish markets, beaches, and restaurants. Ample street parking is available in this area. The sleeping arrangements are a queen-size bed in one bedroom and single bed in the other. Pets are allowed to join you when staying in this rental cottage.

Guest House in Converted Barn - Tisbury
Credit: Vrbo.com
Guests give this rental home rave reviews

Guest House in Converted Barn - Tisbury

Available to rent for two people via Vrbo, this barn measures 696 square feet and has one bedroom and one bath for travelers to Martha’s Vineyard. The property is located in downtown Vineyard Haven on the historic grounds of the Captain John A. Swain House. It has a sleeping loft with a king-size bed on the second floor, above the open living, dining, and kitchen area on the first floor. You can get around on foot and by bike, so it’s not necessary to bring a car. Guests also enjoy the back deck and garden to spend time outdoors here.

Martha's Vineyard Getaway Cottage - Tisbury
Credit: Airbnb.com
There's nothing more perfect than an island cottage here

Martha's Vineyard Getaway Cottage - Tisbury

Five people can stay at this Martha’s Vineyard cottage in Tisbury that has two bedrooms and one bath. It’s on a private, wooded lot with lovely furnishings. The home has fireplaces, a kitchen, laundry machines, internet, TV with cable and streaming capabilities, and more amenities. One bedroom has a queen-size bed, and the other has two single beds. It’s easy to walk from here to the trails, beaches, and West Chop Lighthouse. The rates to stay here vary based on the season.

Perfect for Family, Friends, or a Romantic Getaway - Oak Bluffs
Credit: Vrbo.com
Charming decor your an authentic stay

Perfect for Family, Friends, or a Romantic Getaway - Oak Bluffs

With 1,600 square feet of space, four bedrooms, and two bathrooms, this Vrbo vacation rental sleeps seven people in Martha’s Vineyard. It’s an attractive house with beautiful landscaping and location less than a mile from town. Your stay here comes with walk-in closets, TVs, speakers, board games, and brick fireplace. The host even provides boogie boards to take to the beach, a gas grill, and picnic benches for outdoor dining. Children are welcome to stay here, so it’s a great base for a family getaway.

Vineyard Retreat: An All Season/Pet Friendly House - Tisbury
Credit: Airbnb.com
A large space for your whole group

Vineyard Retreat: An All Season/Pet Friendly House - Tisbury

Larger groups up to eight people can book this Airbnb vacation rental that has three bedrooms, five beds, and 2.5 baths. The home is a mile from Vineyard Haven, so it has a country vibe but is still close to town. Dogs love staying here with their owners. The space offers a modern kitchen, air conditioning, outdoor shower, walk-out basement, TVs and DVD players, and two large outdoor decks. Owen Little Way Beach is about a 0.6-mile walk away from the home. Book this property for a sunny and spacious home with the owners close by in case you need anything.

Ocean Park Victorian - Oak Bluffs
Credit: Airbnb.com
Take a seat and relax on your vacation

Ocean Park Victorian - Oak Bluffs

You can rent this private guest suite in a Victorian home and have your own private entrance to a sunny bedroom on the second floor. The Airbnb rental comes with a private bath with tub and a shared outdoor shower for after the beach. The host provides breakfast and coffee supplies, and you’ll be within easy walking distance of the beach, shops, restaurants, and ferries. The beach is just a three-minute walk away, and downtown Oak Bluffs is about five minutes away on foot. The room has a double-size bed and sleeps two people. Amenities offered include Wi-Fi, TV with cable, air conditioning, and free parking.

Martha's Vineyard Studio Cottage - Tisbury
Credit: Airbnb.com
Surrounded by trees and peacefulness

Martha's Vineyard Studio Cottage - Tisbury

This is one of the many adorable vacation rental cottages in Martha’s Vineyard and a studio space for two people. It’s an Airbnb rental on a quiet woodland property that’s a quarter mile from the main road. It’s just a five-minute walk from here to the Lagoon, and the bike path, YMCA, and performing arts center are all close by too. From here, you can drive to the local beaches in about 10 minutes. The interior of the cottage offers a kitchen, Wi-Fi, TV, and air conditioning. There’s a parking space in the driveway for your vehicle.

Martha's Vineyard Cozy Getaway near Picturesque Philbin Beach - Aquinnah
Credit: Vrbo.com
Walk to the beach from this peaceful rental

Martha's Vineyard Cozy Getaway near Picturesque Philbin Beach - Aquinnah

For your stay in Martha’s Vineyard, consider this 1,200-square-foot house that sleeps eight people. It’s a popular Vrbo rental with three bedrooms and two full baths. The home also has a walk-out basement, deck, fire pit, and outdoor games to play. It is a pet-friendly rental for well-behaved pets. Philbin Beach is about two miles away from this home, and the host provides beach chairs and a cooler you can use. It’s located in Aquinnah for a tranquil stay near the Gay Head Lighthouse. Children are also welcome here, and the home comes with laundry machines, internet heat, and air conditioning.

Classic Martha's Vineyard Cottage - Tisbury
Credit: Airbnb.com
A relaxing spot to unwind at the end of the day

Classic Martha's Vineyard Cottage - Tisbury

Up to three people can stay in this Martha’s Vineyard cottage that has a bedroom with a king-size bed, plus a pull-out sofa in the common area. It’s a great little getaway spot if you’re looking for quiet time and a private space. You’ll be just off the bike path and bus route for easy accessibility. The outside space has a patio, small deck, and outdoor shower. From the cottage, you can walk to Vineyard Haven’s Main Street in about 15 minutes. Shops, restaurants, and a small beach are all close by. Other perks of this rental are the kitchen, Wi-Fi, TV, and laundry machines.

Private Wooded Hillside New and Spacious Studio - Tisbury
Credit: Airbnb.com
A spacious place to spread out and enjoy

Private Wooded Hillside New and Spacious Studio - Tisbury

With this vacation rental, you’ll get a large studio apartment that has a country vibe but is still close to town. It’s in a private and wooded location on the ground level of the host’s home. You’ll have your own entrance, kitchen, and large deck. The hosts live upstairs, but it’s still quiet here. Book this Airbnb to have an open floor plan layout with a queen-size bed, large TV, yoga mats, and renovated space all to yourselves. It comfortably accommodates two guests and also has free parking.

Tiny House with Great Pond Access - Edgartown
Credit: Airbnb.com
How adorable is this tiny setup?

Tiny House with Great Pond Access - Edgartown

Located in Edgartown, this Martha’s Vineyard vacation rental is a unique tiny house that’s 250 square feet in size. While most local rentals are quaint cottages, this listing offers a fun opportunity to live the tiny lifestyle in a wooded location. It’s a place to disconnect and enjoy nature, which means no Wi-Fi. The space has a modern composting toilet, small kitchen with some appliances, indoor and outdoor showers, queen-size bed, and indoor eating area. There’s also an outside deck with a table, chairs, and grill. Bring some water shoes to protect your feet from the bottom of the pond if you want to use the complimentary kayaks on the pond. The tiny house sleeps two people and allows pets.

In Town Queen Room - Oak Bluffs
Credit: Airbnb.com
Take a step back in time with a stay here

In Town Queen Room - Oak Bluffs

Another unique way to experience Martha’s Vineyard is to stay in a room in the Attleboro House, which is a historic inn among the Gingerbread Cottages and on the Oak Bluffs harbor. It’s a prime place to be when you visit Martha’s Vineyard and was renovated in 2018, while still retaining many of its original details that date back to 1874. It’s fun to sit on the wrap-around porch to enjoy the views of the Nantucket Sound and harbor when you stay here. The room accommodates two people and comes with Wi-Fi and air conditioning.

Unique Vineyard Tiny House “The Banana Stand” - Edgartown
Credit: Airbnb.com
Switch up your stay with something unique and fun

Unique Vineyard Tiny House “The Banana Stand” - Edgartown

Another fun tiny house option in Martha’s Vineyard is this “Banana Stand” just two miles from downtown Edgartown. It has a private entrance and parking spot, as well as a kitchenette, outdoor shower, full-size sofa bed, Wi-Fi, and outdoor fireplace and grill. The bathroom has a composting toilet, and there’s an outdoor shower. The Airbnb hosts live on the same property as the tiny house year-around but give guests plenty of privacy and complete separation of spaces. This is a pet-friendly tiny house rental.

Cozy Cottage - West Tisbury
Credit: Airbnb.com
Feels just like home away from home

Cozy Cottage - West Tisbury

Here’s a highly rated vacation rental cottage for two people in West Tisbury. It’s in a quiet, country setting with a bus stop nearby. Guests have a double-size bed in a loft that requires climbing some stairs. There is also a single bed in the living room. The host lives in the cottage when there are not guests staying here. Book this rental property for a peaceful stay and all the comforts of home, including a kitchen, Wi-Fi, air conditioning, and TV with cable.

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