How to Find the Best Summer Rental Home on Martha’s Vineyard 2023

Looking for the perfect Summer luxury rental home on Martha’s Vineyard for summer vacation 2023? 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 2023 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.

summer on the vineyard is the perfect setting for a luxury vacation

But from Memorial Day through Labor Day, the Vineyard transitions from a quiet fishing haven into a vibrant, star-studded vacation destination. And with the premiere of the new Bravo show “Summer House: Martha’s Vineyard” this small island will be seen by a whole new audience. 

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

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 choices are excellent.

Available Rentals:  

Enjoy sweeping views of the harbor from this 4-bedroom house as well as from the two covered porches. Want to be right on the water? This 5-bedroom house is perfect for an ideal few weeks of summer as it has its own private dock. Watch the boats go by from the roof deck or a rainy night hang out in the media room or the exercise room!  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.

Best Hotels:

The Harbor View; Winnetu; Charlotte Inn; Vineyard Square ; The Christopher, The Hob Knob Hotel

Favorite Restaurants: 

Atria; The Port Hunter; 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 Inkwell Beach.

Available Rentals:

This 6-bedroom gingerbread house is classic Oak Bluffs with its architecture and welcoming lavender color.   Enjoy the water view of Vineyard Sound from the oversize wrap porch, the living room, or the master bedroom and then take a break on the rockers, porch swing, cafe table and wicker chairs on the porch. Perfect for a couple or two without kids this 3-bedroom house is right on the beach. The house is located on East Chop and is just a quick walk to the Oak Bluffs town center. This 4-bedroom house is perfect for a family who loves to be outside with its dock, deep water mooring, a private beach as well as deep water access and marina facilities close-by. You will have a great view Lagoon Pond with sunsets to boot. Gather in the large custom kitchen for long, relaxed meals together. 

Best Hotels:

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

Favorite Restaurants:

Sweet Life Cafe; Giordano’s; Red Cat Kitchen

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.

Available Rentals: 

Perfect for a small family or two couples this renovated 2-bedroom residence with open living, kitchen and dining area has a lovely yard with patio, outdoor seating and grill. Plus you are within walking distance of Vineyard Haven. 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.

Luxury Hotels: 

The Mansion House; Crocker House Inn; Nobnocket Boutique Inn

Favorite Restaurants: 

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

Up-island Martha’s Vineyard summer home rental options

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 beautiful Aqunnah retreat is a palatial house that can sleep 8! There are plenty of things to do inside the house but there is an also an outdoor shower, Herb and Veggie Garden’s you can pick and eat from, a fire pit and a patio for warm, long summer nights. 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.

Luxury Hotels: 

Outermost Inn

Favorite Restaurants: 

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:

For a truly unique experience consider this 5-bedroom, 3½ bath, newly renovated farmhouse with a backdrop of Chilmark stonewalls plus a key to the private South Shore Hancock Beach! When you aren’t at the beach sit out at the enclosed which leads to a lovely, private bluestone patio. Another amazing find in Chilmark is this 4-bedroom home in an original Yankee Barn located off South Road. With a cathedral living room as well as a wrap-around deck and an outdoor shower. You’ll need it as you can zip over to the beaches at Lucy Vincent, Menemsha and Squibnocket! For those enjoying a summer romance, check out this sweet 1-bedroom cottage with residential access to Lucy Vincent and Squibnocket beaches.

Luxury Hotels. 

Menemsha Inn & Cottages; Beach Plum Inn

Favorite Restaurants. 

Beach Plum Inn Restaurant; Chilmark Tavern

3. West Tisbury 

West Tisbury is 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.

Available Rentals:

This 4 bedroom-house will give you an amazing Vineyard summer. Complete with a covered porch, all teak furniture, loungers, gas grill, sundeck and out door shower. This 4-bedroom with an indoor pool is a true luxury abode. 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.

Luxury Hotels:

Lambert’s Cove Inn

Favorite Restaurants:

State Road Restaurant; 7a

Finding the Best Luxury Summer Rental Home on Martha’s Vineyard 2023

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.