Looking for the perfect luxury rental home on Martha’s Vineyard for summer vacation 2022? Have a look at our 9-step guide to finding the perfect luxury rental. And assess which of the 5 social circles 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! Let’s make some plans. Here’s how to find the best luxury summer rental home on the island of Martha’s Vineyard for vacation 2022 for you, your family and friends.
martha’s vineyard basics to know before you choose your summer rental home
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.
what is “up-island?” and what is “down?”
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.
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.
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.
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.
Down-island Martha’s Vineyard summer home rental options
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 choices are excellent.
We want to rent this elegant home with 4 bedrooms, chef’s kitchen, pool and hot tub with 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.
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 Inkwell Beach.
This brand new 5-bedroom house with gorgeous ocean views would be perfect for an active family with access to paddleboards, kayaks and tennis courts. 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.
3. Vineyard Haven (aka Tisbury)
Vineyard Haven is the main port of entry to Martha’s Vineyard if you arrive by ferry. It boasts a really fun and diverse Cultural District with creative businesses including design, architecture, wooden shipbuilding, home goods, handcrafts, theater, music, film, and one-of-a-kind boutiques. It’s a charming historical area with a touch of bohemia.
We wouldn’t mind sitting in the spacious 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.
Up-island Martha’s Vineyard summer home rental options
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.
This brand new construction with 4-bedrooms has endless views of the Vineyard Sound and beyond. An outdoor shower, jacuzzi and sauna complete this spectacular, modern home.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.
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.
With miles of hiking trails and the best vineyard beach at your doorstep, this 4-bedroom house also has a 4ft “play” pool that’s perfect for the kiddos. 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.
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.
Old-world charm abounds at this Sea Captain home, a few steps to the famous Vineyard Farmer’s Market. 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. Set back off Main Street offering field and pond views with an abundance of privacy, this grand 5-bedroom home is perfect to gather with friends and family.
Finding the Best Luxury Summer Rental Home on Martha’s Vineyard 2022
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, and fitness. Julie lives in New York 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.
Join our community
For access to insider ideas and information on the world of luxury, sign up for our Dandelion Chandelier newsletter. And see luxury in a new light.