Where to stay around Oak Bluffs?

Our 2018 property listings offer a large selection of 1,677 vacation rentals near Oak Bluffs. From 1,258 Houses to 172 Bungalows, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Oak Bluffs for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Oak Bluffs?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Oak Bluffs:

  • Katama: 267 vacation rentals
  • Woods Hole: 156 vacation rentals
  • Osterville: 281 vacation rentals
  • Buzzards Bay: 187 vacation rentals
  • West Falmouth: 92 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Oak Bluffs?

HomeAway offers a large selection of vacation rentals near lovely places in Oak Bluffs. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Inkwell Beach: 2,434 vacation rentals
  • Oak Bluffs Town Beach: 2,464 vacation rentals
  • Oak Bluffs Harbor: 2,450 vacation rentals
  • Ocean Park: 2,429 vacation rentals
  • East Chop Light: 2,515 vacation rentals

But there are many other points of interest around Oak Bluffs listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Oak Bluffs?

Yes, of course. HomeAway has 1,258 Houses in Oak Bluffs. Our other popular types of vacation rentals in Oak Bluffs include:

  • Bungalows: 172 rentals available
  • Cottages: 172 rentals available
  • Cabins: 172 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments 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 282 vacation rentals with pool available in Oak Bluffs. Please use our search bar to access the selection of vacation rentals available.

    Take the ferry to fun at Oak Bluffs

    If you're heading over to Martha's Vineyard, the chances are Oak Bluffs is where you'll step off the ferry. And there's probably no need to go further. Oak Bluffs—with its placid beaches, its ice cream parlors piled with fancies, and its streets lined with gingerbread cottages—has plenty to delight visitors. There are also carousels to ride, fishing boats to hire, and winding lanes to bike down. No wonder that Oak Bluffs vacation rentals top the list for places to stay on MV, especially for those with kids.

    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.

    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—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.

    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.