Oak Bluffs Guest Houses

A row of colorful, historic houses with a central path.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Oak Bluffs guest houses

A cozy living room with a fireplace, bookshelves, a dining area, and a staircase.

1. Madison Inn

Oak Bluffs

Melissa

includes taxes & fees

8 Nov - 9 Nov

A residential property with a gravel driveway, a wooden bench, and a house with a shingled exterior.

2. The Lightkeepers Inn

Edgartown

Penny

includes taxes & fees

18 Nov - 19 Nov

A house with a white door, a mailbox, and a sign reading '270 Ocean Ave.'

3. Sea Breeze Inn

Hyannis

Ann

includes taxes & fees

17 Nov - 18 Nov

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Oak Bluffs Hotel Reviews

Faraway Martha's Vineyard

10/10 Excellent

"Overall excellent option right in downtown Edgartown. Beautifully decorated. Extremely clean. Service was impeccable. The two bedroom option is amazing. decorated with class and spacious overlooking the pool and views to the bay."

Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs

10/10 Excellent

"The house was amazing, the communication with the host superb, and the proximity of the space to Oak Bluffs, Vineyard Haven/Oak Bluff ferry terminals, shops and locations was unbeatable. It’s a must see and stay if you are planning a family trip."

Find out more about Oak Bluffs