Bed & bath: 4 bedrooms, 3 baths
Top amenities: Private beach access
Nearby attractions: 100 acres of conservation land

Sometimes it's good to have separate spaces when you’re traveling with family or as a group. This listing has both a three-bedroom main house and a one-bedroom guest cottage. The best part? This house abuts Sherriff’s Meadow, 100 acres of conservation land that is great for hiking during the day and supremely tranquil after dark.

Bed & bath: 4 bedrooms, 3.5 baths
Top amenities: A pool, renovated entertainment barn, and indoor-outdoor Bluetooth sound systems
Nearby attractions: Bad Martha Farmers Brewery

Being walking distance from all that Edgartown has to offer makes this spacious home a great choice for groups—no need to fuss over taxis or rental cars. And you know how sometimes a few members of the group want to go to bed early, while others want to keep the party going? This property solves that problem, with a detached “entertainment barn,” complete with beanbag chairs and table tennis.

Bed & bath: 4 bedrooms, 2 baths
Top amenities: Backyard with a barbecue area for alfresco dining
Nearby attractions: Downtown Oak Bluffs, the beach

On an island where everything feels charming, this Victorian beach house more than delivers, with classic lace trim and a pink exterior, plus a funky interior with turquoise floors and eclectic furniture. It’s located in the historic Copeland District of Oak Bluffs, with both town and beach just steps from the front door. Walk to everything—or take in the sights and people watch from the comfort of your own wraparound porch.

Bed & bath: 3 bedrooms, 2 baths
Top amenities: A literal sailboat, all to yourself
Nearby attractions: Vineyard Haven Harbor

Ever dream of overnighting on a working sailboat? Now’s your chance—and in the summers, this vessel is anchored in Vineyard Haven Harbor, so you can enjoy Below Deck style accommodations with all the convenience of Vineyard Haven at your fingertips.

Bed & bath: 3 bedrooms, 1 bath
Top amenities: A large yard with lawn games and a grill
Nearby attractions: Bike rentals, a library, mini-golf

Any cottage cheekily titled “Not Your Great Aunt’s Island Cottage” sounds like a winner to us. The interiors are tastefully updated and decorated with nautical-inspired decor, and there’s an elegant, large backyard that’s simply yearning for lawn games that go from day to night—and a grill for cookouts, too.

Bed & bath: 3 bedrooms, 1.5 baths
Top amenities: A fully stocked kitchen and a fenced yard for children and pets
Nearby attractions: Unbelievable sunsets off the island’s west end beaches

Many come to the Vineyard for the charming Victorian houses and old New England flair, but don’t sleep on the prospect of staying in a more modern house—this one has an enormous wall of windows off the kitchen and living room that really brings the outside in. If you’re traveling with little ones (of the human or animal variety), this property has a great fenced-in yard so they can run free.

Bed & bath: 4 bedrooms, 3 baths
Top amenities: Spacious patio complete with lounge furniture and grill
Nearby attractions: Menemsha village

The cozy proportions of this intimate cottage are just right for a getaway, and filled with old-school details like shiplap walls and antique furniture. The mostly-white interiors are bathed in natural light, making for a soothing atmosphere even on chillier days. Can’t you just imagine cozying up on the deck furniture with your coffee each morning?

Bed & bath: 1 bed, 1 bath
Top amenities: The owner lives in the (separate) main house, and is just a text or door knock away if needed
Nearby attractions: Miles of hiking and biking trails right by your front door

This studio is a solid option for the solo traveler or even a couple. Located a short cab ride from the ferry terminal, the intimate studio space abuts over 30 acres of conservation lands, yet is just minutes from several beaches and restaurants. Spend afternoons going for a bike ride or meandering around nearby trails.

Bed & bath: 4 bedrooms, 3 baths
Top amenities: A reverse-style design with spacious, open-plan second floor perfect for entertaining
Nearby attractions: Located on 1.6 quiet acres near Long Point Beach and Long Point Wildlife Refuge

This unique property features a “reverse-style” design where bedrooms are on the ground floor and common spaces are on the second floor. So when you’re together as a group, cooking in the open kitchen or playing boardgames in the sitting area, there is an abundance of natural light and surrounding trees that contribute to a sense of privacy.

Bed & bath: 4 bedrooms, 2 baths
Top amenities: A secluded, (basically) private beach
Nearby attractions: Menemsha village

While some might consider the Victorian-style cottages quintessentially Martha’s Vineyard, locals know that retro, midcentury spaces are equally as indicative of this area. This cute cottage is no exception—with colorful kitchen cabinets, turquoise painted floors, and knotty pine paneled walls. Enjoy water views, as well as a private staircase down to a secluded part of the beach which seldom has visitors.

Bed & bath: 3 bedrooms, 1 bath
Top amenities: New furniture, newly renovated full kitchen and bath
Nearby attractions: Not much, which is why people choose Chappaquiddick

The island of Chappaquiddick—or “Chappy”—is not for every traveler. It’s located a two-minute ferry ride from downtown Edgartown but feels worlds away. It’s a secluded, private island with its own community of locals, and an even more relaxed and low-key vibe. If you’re looking to truly get away, be a little off-grid, and explore a more natural side to Martha’s Vineyard—where there are not even restaurants or grocery stores—consider booking this secluded cottage.

Bed & bath: 1 bed, 1 bath
Top amenities: Private deck for warm nights, fireplace for chilly nights
Nearby attractions: Seth’s Pond and Ice House Pond

On an island with no shortage of charming cottages, this Martha's Vineyard Airbnb is in a league of its own—near an organic garden, walking distance to freshwater swimming ponds, and with a real woodburning fireplace. When the surf is high, you can even hear waves crashing in the distance. It’s a pretty minimal setup with just a mini-fridge, coffee maker, and microwave on site (coffee and tea provided!), but this is the kind of cottage for people who prefer to do their own exploring anyway.

Bed & bath: Studio, 1 bath
Top amenities: Incredibly close harbor views
Nearby attractions: All the shops and restaurants Oak Bluffs has to offer—but especially Back Door Doughnuts

One of the best parts of visiting an island is observing daily life, and the comings and goings of its inhabitants. This studio, located on a pier in Oak Bluffs, is in the literal center of the action. If offers excellent harbor views—“You cannot get closer to the harbor unless you fell in,” reads the listing—and there’s even room service (of sorts): This studio is located on top of the Lobsterville Bar & Grille, which will deliver to you.