The town of Oak Bluffs lies on the island of Martha’s Vineyard and is a popular tourist destination during the summer months, home to the largest marina on the island. Choose from over 900 Oak Bluffs vacation rentals and find your dream accommodation with FlipKey.

About Oak Bluffs

The pretty Gingerbread Cottages here have appealed to vacationers for over 100 years, and it’s easy to see why this quaint and charming town remains such a popular destination. With ferries arriving at the harbor from the mainland several times a day, families and couples come to Oak Bluffs for a relaxing break.

Beautiful beaches, rich history to explore and plenty of outdoor activities like golfing, fishing and hiking ensure that Oak Bluffs has everything you need for a great vacation. While you’re here, dine on delights such as fried seafood, blackened catfish and jambalaya. Wash it all down with a beer or root beer from the Offshore Ale Company, the island’s only brewery.

With around 203 sunny days a year, summer is definitely the warmest time to visit the town, but Oak Bluffs is just as beautiful during the Fall. Average summer temperatures are around 78 degrees Fahrenheit.

What to do

The beaches here are simply stunning, whether you head for Oak Bluffs Town Beach or relax on Joseph A. Sylvia State Beach. With two miles of golden sands, the calm waters and views of Cape Cod ensure this is a popular family spot that’s also good for windsurfing.

The marina here is a great spot for drinks and dining, with events like the Harbor Festival held here during the summer months. You’ll find the majority of stores, bars and restaurants on Circuit Avenue.

Don’t miss the chance to see the Flying Horses Carousel, the oldest operating carousel in the US, with hand-carved horses created in 1876.

There are plenty of outdoor activities here, too, with family fishing expeditions leaving from Oak Bluffs Dock and Farm Neck Golf Course with its 18-hole championship course and driving range. Pecoy Point Preserve is also nearby, with 14 acres of trails.

Top Oak Bluffs travel tips

Ferries arrive at the harbor from the mainland from five different destinations in Massachusetts: Falmouth, North Kingstown, Woods Hole, New Bedford and Hyannis.

The best way to explore this compact town is definitely on foot, but there is a bus service, or you can rent a bike or moped in the town center. There’s also a free pedicab service, with any tips and donations going to charity.

Beautiful beaches, family-friendly restaurants and outdoor activities continue to draw visitors to Oak Bluffs year after year.

Why not book a vacation rental with ocean views on FlipKey today and come find out what Oak Bluffs has to offer?