Book Holiday Homes in Oak Bluffs
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Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Oak Bluffs

Cape Cod cottage

Coastal chic meets French Provençal in this newly renovated oceanfront home.

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry

Historic Oak Bluffs home, short walk to town, beach, and harbor.

Gorgeous Spacious Victorian Cape Code Beach View Retreat

Charming coastal home with large yard, firepit, & grill - pool and beach access

Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

Coastal townhome with easy beach access, beach gear, balconies, grill, W/D, & AC
Oak Bluffs Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oak Bluffs vacation homes are the perfect way for you to wing it.
Holiday houses in Oak Bluffs let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oak Bluffs in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oak Bluffs adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oak Bluffs with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oak Bluffs vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Oak Bluffs Holiday Homes essential information
Accommodation | 1353 Holiday Homes |
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Lowest Price | AU$311 |
Highest Price | AU$1,480 |
Popular accommodation | Cape Cod cottage, Coastal chic meets French Provençal in this newly renovated oceanfront home. , Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches, Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry, Historic Oak Bluffs home, short walk to town, beach, and harbor., Gorgeous Spacious Victorian Cape Code Beach View Retreat, Charming coastal home with large yard, firepit, & grill - pool and beach access, Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown, Coastal townhome with easy beach access, beach gear, balconies, grill, W/D, & AC |
Holiday Homes in Oak Bluffs
More accommodations in Oak Bluffs
Top trending hotels in Oak Bluffs

Summercamp

Morgan Hotel

The Attleboro House

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
More ways to explore Oak Bluffs
Top picks
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.