Discover a selection of 1,500 vacation rentals in Oak Bluffs, MA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including air conditioning and swimming pools. Prices start at $143 per night, and houses and cottages are popular options for a stay in Oak Bluffs. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Oak Bluffs
Destination guide

Enjoy a cabin rental in Oak Bluffs

Oak Bluffs is a town located in the heart of Martha's Vineyard island. This means that if you love wine, you'll find it right outside the front door of your lake cabins for rent in Massachusetts. You can walk the vineyards and get back to nature in a quiet, serene, and refined environment while still being within easy access of all the fine dining, shopping, beaches and other attractions nearby. In the evenings, you can relax with the comfort and amenities of your cabin. Recharge those batteries, and just enjoy everything that life has to offer before adventuring again tomorrow.

Things to do

Gingerbread treats and flying horses in Oak Bluffs

Many Oak Bluff vacation rentals lie on the north side of town, near the iconic white lighthouse tower of the East Chop Light. It has fantastic views back across to Falmouth. Seaside views are one thing, but it's a one-time religious camping ground that has the real eye candy here. The so-called 'gingerbread cottages' are as brightly colored as they are tiny, and were built by 19th-century Methodists in the vivid Gothic Carpenter style. Kids and parents will be all awhirl after a ride on the Flying Horses Carousel, the oldest operating merry-go-round in the country.


Oak Bluffs—simple seaside pleasures

As a town surrounded on three sides by the sea, much of what goes on in Oak Bluffs involves a healthy mix of sun, sea, and sand. Picnic hampers and spades at the ready, then, for days of paddling, sunbathing, and snacking next to sun-spangled waves. The more active-minded can grab a paddle, and head out in a kayak or on a paddleboard since the waters are calm here. Then there are lungfuls of fresh, salt-tanged air to invigorate those taking fishing trips around the area. And greens with a view greet those teeing up at Oak Bluffs' scenic golf course.


Oak Bluffs—a walk on the mild side

The Atlantic Ocean plays a big role in Martha's Vineyard weather, helping to keep this Massachusetts island relatively mild, whatever the season. If you've booked Oak Bluffs vacation rentals to make the most of the beach, July or August are ideal: expect a warm 70-80°F with few rainy days. September is only slightly cooler, a rather pleasant 70°F, and you'll notice the streets and ice-cream parlors are a little less crowded. And while spring may be fresh, it is the perfect time enjoy an outdoors Oak Bluffs break, glowing at its verdant best.

Natural features

The bays and birds of Oak Bluffs

It's out in the bays surrounding Martha's Vineyard that nature is at its wildest. Boats can be hired to whisk you out to spot whales or dolphins. On land, Oak Bluffs presents its softer side, with its gently rolling fields, woods, and meadows. These slip into marshes or dune banks where they meet the sea. There are some wonderful birding chances at nature preserves like Felix Neck Wildlife Sanctuary, with swans, kestrels, and heron being common. And by the shore, you may find crabs, clams, shrimp, or even the primal and bizarre horseshoe crabs.

How to get there

Transportation options to and around Oak Bluffs

Fly into Vineyard Haven, MA (MVY-Martha's Vineyard), the closest airport, located 4.1 mi (6.7 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Hyannis, MA (HYA-Barnstable Municipal), which is 21.5 mi (34.5 km) away.

How many vacation rentals are available around Oak Bluffs, MA?

Our 2022 property listings offer a large selection of 1,449 vacation rentals around Oak Bluffs. From 1,237 house rentals to 99 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Oak Bluffs?

Yes, of course. Vrbo has 1,237 Houses in Oak Bluffs. Our other popular types of vacation rentals in Oak Bluffs include:

  • Cottages: 99 rentals available
  • Condos/Apartments: 106 rentals available
  • Cabins: 99 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Oak Bluffs?

Yes, you can select your preferred vacation rental with pool among our 281 vacation rentals with pool available in Oak Bluffs. Please use our search bar to access the selection of vacation rentals available.