How to Find a Perfect Rental on Martha’s Vineyard 2019

Looking for the perfect home to rent on Martha’s Vineyard for summer 2019? Have a look at our 9-step guide to finding the perfect luxury rental. And assess which of the 5 tribes of Martha’s Vineyard is yours. Then check out some of the specific fun facts and good things to know that we’ve uncovered, as well as some specific properties that are currently for rent that caught our eye. Summer’s almost here!

martha’s vineyard basics

Bathed in beauty, the island of Martha’s Vineyard is roughly four times the size of Manhattan and divided into “up-island” and “down-island.”

As with most long-held vernacular traditions, the term is a bit misleading and does not actually refer to North and South. Rather it is a vestige of the Vineyard’s whaling days where heading “up” in nautical terms takes you west.

Up-island encompasses the rural farms and pastoral towns of West Tisbury, Chilmark and Aquinnah. Down-island is the decidedly more bustling residential and commercial heart of the island and includes the towns of Edgartown, Oak Bluffs and Vineyard Haven.

Edgartown, Martha’s Vineyard

Martha’s Vineyard is home to 15,000 people year round, including The Aquinnah Wampanoag Tribe of Gay Head who have called the island their home for over 10,000 years.

But from Memorial Day through Labor Day, the Vineyard transitions from a quiet fishing haven into a vibrant, star-studded vacation destination.

Despite the glamour element, though, the Vineyard remains untouched by the kind of rampant commercialism found in other beach towns. There’s not a single chain restaurant or cookie-cutter motel in sight.  Rather, you’ll find cozy inns and small restaurants focused on truly local farm to table cuisine. The vibe is nonchalant, friendly and unpretentious. That’s one of the reasons that it’s become a preferred getaway of Presidents and celebrities alike.

Oak Bluffs, Martha’s Vineyard

Below, we’ve highlighted the three Up-island and three Down-island towns and included a couple of our favorite rentals that still have some summer weeks available at the time of writing. Plus the hotels and restaurants we love in each.

If it helps you narrow down which town you’d like to stay in, here’s an insider tip: the Vineyard is “dry,” except for Edgartown and Oak Bluffs.


1. Edgartown 

Edgartown has emerged from its whaling past to become the most upscale town on the island. Throughout the center of town, you’ll find the stately well-preserved homes of 18th and 19th-century whaling captains, surrounded by manicured lawns and gardens. Further out, there are secluded properties surrounded by woods, some with private beaches. The nearby public beaches include a few quiet hidden gems, as well as the always popular South Beach, on the Atlantic in the Katama section. And the dining choicesare excellent.

Available Rentals:  

We want to rent this elegant, waterfront captains home with 5 bedrooms, chef’s kitchen and pool with 4 of our best girlfriends for a summer escape. For families, this 5 bedroom gem is set on 3-private acres with nearby walking trails and access to canoeing the calm waters of Oyster Pond. If you’re a couple looking to be in the heart of Edgartown, this well-appointed 2 bedroom apartment looks to be a wonderful home base to have a romantic beach week.


The Harbor View; WinnetuCharlotte InnVineyard Square ; The Christopher, The Hob Knob Hotel


AtriaThe Port Hunter19 Raw Oyster Bar; The Newes From America Pub, The Covington, Right Fork Diner, l’etoile


2. Oak Bluffs

Oak Bluffs is one of the two ferry ports on the Vineyard, and home to the historic Victorian cottages of the Methodist Campground, Illumination Night, the charming Ocean Park, and Circuit Avenue with its shops and restaurants. It’s also the historic center of the black community’s long residence on the island, and the beloved Bay-side beach, The

Available Rentals:

Rustically charming, this 4-bedroom home looks like an overgrown tree house. It would be perfect for a family with young children as it’s only a 5-minute walk to the beach. For multiple families and larger groups of friends, check out this whimsically decorated 6-bedroom historic home, with its own private dock and beach. And here’s your chance to stay in one of Oak Bluffs’ famous Victorian Gingerbread cottages. With 4-bedrooms, it is only 2 blocks away from Inkwell Beach.


Summercamp; Pequot Hotel; The Oak Bluffs Inn; Dockside Inn


Sweet Life Cafe20ByNineGiordano’s; Red Cat Kitchen

Oak Bluffs

3. Vineyard Haven

Vineyard Haven is the main port of entry to Martha’s Vineyard if you arrive by ferry.  Although the year-round population is only about 2,000 people, its population increases substantially in the summer. You’ll find great restaurants, bookstores and other fun shoppingin this busy harbor town.

Available Rentals: 

We wouldn’t mind sitting in the spacious, enclosed porch of this classic 5-bedroom home with our favorite book all day while the kids play on the private beach below. If you’re dreaming of a solo getaway, this cozy 1-bedroom guesthouse is immaculate and tastefully decorated. This sprawling and open 5-bedroom home overlooks the harbor with steps down to a private beach and is located 1-mile from town.


The Mansion HouseThorncroft Inn; Crocker House Inn; Nobnocket Boutique Inn


The Net ResultBeach RoadThe Black Dog Tavern; Grace Episcopal Church Lobster Rolls (Yes, you read that right.  Available Fridays only); Little House Café

Vineyard Haven


1. Aquinnah 

At just six square miles, Aquinnah is the smallest town on Martha’s Vineyard and is best known for the Gay Head Cliffs, colorful clay cliffs that stretch for a mile over Moshup Beach. Jackie Kennedy and her family maintained a large residence there for many years, and the Native American population on the island is centered here, too.

Available Rentals: 

This brand new construction with 5-bedrooms has endless views of the Vineyard Sound and beyond. We’d happily soak up the serene Scandinavian vibes of this 4-bedroom home with a pool all summer long. Atop one of the highest points on the island, this updated 3-bedroom farmhouse is a perfectly secluded retreat that is situated on 6 acres and surrounded by nature paths. If you are looking for quiet inspiration, look no further than this traditional waterfront location.


Outermost Inn


Outermost Inn Restaurant; Aquinnah Shop Restaurant


2. Chilmark 

Chilmark is where President Obama and his family spent most of their August vacations while he was in office. This part of the island is rugged and rural with hilltop water views, picturesque sandy beaches and ancient stone walls framing the landscape.  Property rental within Chilmark allows you access to two of Martha’s Vineyard’s best Atlantic beaches: Lucy Vincent and Squibnocket. The sunsets here are staggeringly beautiful – people plan entire afternoons around securing a great spot from which to view them.

Available Rentals:

Located on Chilmark Pond, this traditionally decorated 4-bedroom home is newly constructed and offers renters the key to Hancock Beach, a private beach that never gets crowded and is a great place for swimming. If you’re looking to get a few families and friends together but still want some alone time, this unique property is constructed of several cottages joined together by multiple common rooms and light-filled hallways. It has 6-bedrooms with deeded private beach access. For those enjoying a summer romance, check out this sweet 1-bedroom cottage with residential access to Lucy Vincent and Squibnocket beaches.


Menemsha Inn & Cottages; Beach Plum Inn


The Homeport; Beach Plum Inn Restaurant; Chilmark Tavern


3. West Tisbury 

Home to acres of bucolic rolling farmland, state forests, and scenic beaches, in West Tisbury you’ll find serenity and a neighborly sense of community. It’s also the site of the wonderful annual Agricultural Fair in mid-August.


Feast your eyes on this stately 4-bedroom home that features a kitchen with two gas burning cooktops and two ovens. Invite your friends who love to cook and bake while you sneak away to swim in the pool! This contemporary 3-bedroom cottage with open, vaulted living room and kitchen ceilings, feels like the perfect spot to spend quality time with your family. Full of character, this recently renovated 1810 farmhouse still retains its old wood beams, pine floors and fireplaces. With 6-bedrooms, it can accommodate a rotating roster of guests who will surely want to come to visit.


Lambert’s Cove Inn


State Road Restaurant7a

West Tisbury

There you have it. A quick walk through the various ways to spend blissful summer days on the Vineyard. Happy house hunting! We’ll see you at Morning Glory Farm.

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Crediting her training as a cultural anthropologist at Wellesley College, Julie has immersed herself in various industries in the last 15 years including fashion design, event planning, fitness and even investigating police misconduct. Julie lives in NYC where she loves trying every ramen and dumpling restaurant with her husband and three children. She finds joy in bold prints, biographies of fierce women, kickboxing and spending way too long finding the perfect polish color to express her mood.

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