Book Holiday Homes in Oak Bluffs
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Featured Holiday Homes in Oak Bluffs

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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

Updated house close to town and beach with patio, AC, and games

Cozy cottage 3/4 mile from Oak Bluffs harbor

Coastal home with outdoor shower, grill, fireplace, central AC, & W/D

The quintessential MV home. Now booking for 2026!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Luxury Loft Historic Center Oak Bluffs
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 | 1299 Holiday Homes |
|---|---|
Lowest Price | NZ$1,549 |
Highest Price | NZ$2,101 |
Popular accommodation | Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs, MOST CHIC SPOT! Your Martha's Vineyard Getaway!, Historic Oak Bluffs home, short walk to town, beach, and harbor., Updated house close to town and beach with patio, AC, and games, Cozy cottage 3/4 mile from Oak Bluffs harbor, Coastal home with outdoor shower, grill, fireplace, central AC, & W/D, The quintessential MV home. Now booking for 2026!, A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!, Luxury Loft Historic Center Oak Bluffs |
Top trending hotels in Oak Bluffs

Summercamp

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Morgan Hotel

The Island Inn on Martha's Vineyard
More ways to explore Oak Bluffs
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.
