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 kitchens. Prices start at $150 per night, and houses and condos are popular options for a stay in Oak Bluffs. Either way, you'll find a rental for everyone's needs.
Destination guide

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.

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 2020 property listings offer a large selection of 1,338 vacation rentals around Oak Bluffs. From 1,076 house rentals to 77 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a seaside property in Oak Bluffs?

Drinking in crisp ocean air, basking in the sun and losing all track of time. Now that's the sort of amazing vacay you deserve. Vrbo has 498 vacation rentals by the beach for you to pick from. Alternatively, you may prefer to try something a little different. Vrbo has oodles of options to choose from, including:

  • 205 water-view vacation rentals.
  • 192 beach vacation rentals.
  • 186 ocean-view vacation rentals.

Can I rent a house in Oak Bluffs?

If you want to live like a local and love a bit of extra space and privacy, renting an entire house is the way to go. There are 904 houses listed on Vrbo. Prices start at $32 a night. If that doesn't fit with your squad's style, we've got a range of other rental options available, such as:

  • Cottage: 87 vacation homes. Prices start from $160 per night.
  • Condo: 50 vacation homes. Prices start from $116 per night.
  • Townhome: 31 vacation homes. Prices start from $193 per night.

Can I stay in Oak Bluffs in a large group?

Whether you're setting off on a vacation with the whole family or spending a week away with your old school mates, it's a whole lot of fun staying under the same roof! The great news is that Vrbo has places to suit. 290 house vacation homes are listed. Currently, they're the leading option here for sizeable groups. Rental options around here that are perfect for large groups include:

  • Are you looking for vacation homes that can fit 8 of you? We have 598 that will fit the bill. Prices start from $193 per night.
  • If you have 6 in your family, you'll be delighted to learn that there are 416 vacation homes that are suitable. Prices start at $116 a night.
  • Planning a trip away with a group of 10? We offer 324 vacation homes that will be ideal. Prices start from $268 per night.

So never fear! When you travel with us you can bring your mom, your cousins and all your mates to Oak Bluffs.

Where are the cheapest rentals in Oak Bluffs?

Those narrow hotel hallways are no place to spend your precious vacation moments! Uncover our value-for-money rentals today and ensure everyone has enough room to spread out. Woods Hole is a good area to consider if you want to keep a handle on your budget. Vrbo has 54 rentals, and the average price is a very agreeable $315 per night. Marstons Mills is another good option. We have 63 rentals here, and the average price is around $329 a night.