12 Summer Vacation Homes for Rent on Martha’s Vineyard That Even Your Mother-in-Law Will Approve of

If you’re looking for a great summer getaway, what could beat a hotel stay on Martha’s Vineyard? How about renting an entire house and bringing the whole family?

If you’re looking for a great summer getaway, what could beat a hotel stay on Martha’s Vineyard? How about renting an entire house and bringing the whole family?

There are plenty of amazing vacation homes for rent on Martha’s Vineyard. Here are 12 of the very best spots available to rent this summer.

Best Summer Vacation Rentals on Martha’s Vineyard

1. Darling cottage with a sundeck in Chappaquiddick (Edgartown)

This three-bedroom cottage in Chappaquiddick offers gorgeous views of Katama Bay and sleeps 6. It has a spacious, open floor plan with sliders that lead to a sundeck and large yard.

Just a short distance to a private, sandy, warm-water beach, it’s a perfect vacation space for families.

2. Artist-friendly sanctuary with a modern flair (West Tisbury)

Set on lush grounds with walking paths and plenty of greenery, this artist-friendly property features light-filled, modern living spaces that include a studio.

With three bedrooms and two baths (one with a claw-foot tub), this newly listed rental in West Tisbury is ideal for anyone who enjoys natural settings.

A lovely deck overlooks the idyllic yard. It sleeps 5.  

3. Contemporary home on a private wooded lot, near preserve (Edgartown) 

Enjoy the seclusion of this contemporary rental property nestled within a quiet, wooded lot. It’s near Felix Neck Wildlife Sanctuary and convenient to Edgartown.

Inside, cathedral ceilings add to the spacious feel of this four-bedroom rental.

Plan some outdoor adventures, biking or hiking, or just relax in the hammock beneath the pines. 

4. Waterfront home with lagoon views, dock, and tennis (Oak Bluffs) 

With peaceful views of a freshwater pond suitable for both swimming and fishing, this beautiful waterfront home has all the makings of a perfect vacation.

From the cathedral ceiling to the gorgeous hardwood floors, it offers every creature comfort. This includes granite countertops and high-end appliances in the kitchen.

A spacious deck, salt-water dock, and association tennis courts complete this four-bedroom property. It comfortably sleeps 6. 

5. Cute 3-bedroom cottage with private beach access (Aquinnah)

This adorable cottage in Aquinnah has both front and back decks, and a 16-foot sliding glass door to create a spacious effect.

Set within a private lot, it features three bedrooms and a well-equipped kitchen. In addition, guests enjoy exclusive access to Gay Head Beach.

6. Classic Cape with historic details & modern conveniences (Edgartown) 

This four-bedroom updated classic is rich in historic details, like the antique wallpaper and beloved library collection. Yet, it provides all the modern amenities.

Located close to the village center and just a ten-minute walk to the beach, it’s on a lovely sloped yard beside the Sheriff’s Meadow nature preserve.

The town dock and Chappaquiddick Ferry are also nearby. Sleeps 5 and has two bathrooms.

7. Condo with unobstructed water views, balcony (Oak Bluffs)  

Enjoy incredible views of Nantucket Sound from the comfort of this contemporary condominium in Oak Bluffs. In the Copeland District, this rental property features an open floor plan, two spacious bedrooms, and two bathrooms. It sleeps 5.

A private balcony and almost every room offer a stunning, unobstructed water view. Plus, it’s a short walk to the beach, shopping, ferry, and Flying Horses carousel.

This property is equipped with elevator service, too.

8. Vineyard style cottage with panoramic views on high (Oak Bluffs)  

Take in panoramic water views of the lagoon and breathtaking sunsets, and Nantucket Sound from this unique three-bedroom rental in Oaks Bluffs. It’s perched 25’ high on a bluff and includes 110’ of private sandy beach.

Guests can kayak, canoe, windsurf, or sail from the cottages’ mooring. Enjoy spectacular views through floor-to-ceiling windows or while dining alfresco on the flagstone patio.

This light-filled, comfortable home has an open floor plan and three well-appointed bedrooms to sleep 5.

9. New England charm in a whaling captain’s home (Edgartown) 

See what it’s like to stay in a Whaling Captain’s home in Edgartown in this stately historic colonial that sleeps 8. This property has been renovated and professionally decorated with attention to preserving its historic charm.

An open floor plan living space features cathedral ceilings, state-of-the-art appliances, and a working fireplace. Each bedroom includes its own en suite bath.

Accommodations provide access to the sauna and fitness center at the inn next door, includes complimentary parking. Daily housekeeping and laundry services are available at this charming colonial in historic Edgartown Village. 

10. Affordable Cape house, quiet neighborhood (Vineyard Haven) 

On a quiet street in Vineyard Haven, this cute four-bedroom, two-bathroom cottage with a screened-in porch is within walking distance of the local shops on Main Street. It features a beautiful lawn and gardens, as well.

11. Upscale property with steam room, sleeps 20 (West Tisbury)

This upscale property between Vineyard Haven and Up-Island offers top-tier appliances, extra amenities, and sleeps 20.

From the expansive kitchen and elegant living spaces to six well-appointed bedrooms, 4.5 bathrooms, a steam room, and two enclosed outdoor showers, guests will enjoy a luxury lifestyle.

This home is on a beautifully manicured property alongside the state forest.  

12. Exclusive home in a gated community with ocean views, fishing (Chilmark)

For the ultimate experience of exclusivity and privacy, enlist this luxurious home in Squibnocket. This rental poised alongside the Atlantic Ocean features an expansive living room with a fireplace, a fully equipped chef’s kitchen, and a master bedroom with an ensuite bath.

Accented by vaulted ceilings and hardwood floors throughout, this four-bedroom, ten-bathroom home sleeps 6 in pure comfort.

Only 10 other properties in this gated community share 1000+ acres of dunes and beaches. The private, undisturbed shores are renowned for excellent striped bass fishing. Enjoy fine food and farm-to-table dining in unassuming venues nearby.

Final thoughts on Martha’s Vineyard rentals for families

No matter which of these twelve properties you choose, you’ll have booked one of the best vacation homes for rent on Martha’s Vineyard! To find a different rental that’s closer to perfect for you, browse additional properties here.