Destination guide

Beautiful Oak Bluffs will entice you

Enjoy the wineries and other features of Oak Bluffs. Travelers like the beaches, shopping and local tours in this walkable and scenic city. With a vacation rental, you get a home away from home—many rentals offer full kitchens and outdoor grills for some home cooking.


Activities and attractions in Oak Bluffs

Do you want to discover top things to see and do during your stay? Venture out of your cozy vacation rental and check out everything that Oak Bluffs has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Farm Neck Golf Club (0.3 mi / 0.6 km)
  • Island Cove Adventures (2.2 mi / 3.6 km)
  • Falmouth Country Club (10.9 mi / 17.5 km)
  • Cape Cod Country Club (12.4 mi / 19.9 km)

Seasonal weather in Oak Bluffs

If you're planning a vacation around warm-weather activities, August, July, June and September are the hottest months to visit, when temperatures average 77°F.

Natural highlights

Exploring the natural landscape of Oak Bluffs

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Oak Bluffs is a great spot to appreciate mother nature. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city center:

  • Inkwell Beach (1.2 mi / 2 km)
  • Ocean Park (1.2 mi / 2 km)
  • Oak Bluffs Town Beach (1.5 mi / 2.4 km)
  • Joseph Sylvia State Beach (1.8 mi / 2.8 km)
  • Tisbury Town Beach (2 mi / 3.2 km)
  • Gus Ben David's World of Reptiles and Birds Park (2.2 mi / 3.5 km)

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.

Where to stay around Oak Bluffs?

Our 2019 accommodation listings offer a large selection of 1,794 holiday lettings near Oak Bluffs. From 1,415 Houses to 168 Cottages, find unique self catering accommodation for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near Oak Bluffs is on HomeAway.

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

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Oak Bluffs:

  • Buzzards Bay: 230 holiday homes
  • West Barnstable: 58 holiday homes
  • Osterville: 316 holiday homes
  • Cotuit: 483 holiday homes
  • Cummaquid: 2,364 holiday homes

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

What are the most popular points of interest and landmarks to stay near when travelling to Oak Bluffs?

HomeAway offers a large selection of holiday accommodations near great places in Oak Bluffs. From HomeAway travellers, the most popular points of interest to stay near are:

  • Oak Bluffs Public Library: 2,549 holiday lettings
  • Cottage Museum: 2,621 holiday lettings
  • Ocean Park: 2,637 holiday lettings
  • Trinity Park Tabernacle: 2,610 holiday lettings
  • Flying Horses Carousel: 2,651 holiday lettings

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 holiday rentals available near the point of interest of your choice.

Can I rent Houses in Oak Bluffs?

Yes, of course. HomeAway offers 1,415 Houses in Oak Bluffs. Our other popular types of Oak Bluffs holiday rentals include:

  • Cottages: 168 self catering accommodations
  • Bungalows: 168 self catering accommodations
  • Condos/Apartments: 117 self catering accommodations

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

Can I find a holiday accommodation with pool in Oak Bluffs?

Yes, you can select your preferred holiday accommodation with pool among our 246 holiday homes with pool available in Oak Bluffs. Please use our search bar to access the selection of holiday rentals available.