Book Holiday Homes in Oak Bluffs

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Featured Holiday Homes in Oak Bluffs

Cape Cod cottage

Cape Cod cottage

Mashpee
With a stay at this vacation home in Mashpee, you'll be within a 15-minute drive of Cape Cod Beaches and Cahoon Museum of American Art.
Cape Cod cottage
Coastal chic meets French Provençal in this newly renovated oceanfront home.

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

East Falmouth
The price is AU$1,480 per night from 1 Apr to 2 Apr
AU$1,480
includes taxes & fees
1 Apr - 2 Apr
When you stay at this vacation home in East Falmouth, you'll be on the beach, within a 15-minute drive of Cape Cod Beaches and Woods Hole Ferry Terminal.
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

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

Chilmark
Located in Chilmark, this vacation home is by the sea, within a 5-minute drive of Waskosim's Rock Reservation and Middle Road Sanctuary.
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
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Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry

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

Falmouth
With a stay at this vacation home in Falmouth (Falmouth Heights), you'll be within a 15-minute drive of Cape Cod Beaches and Woods Hole Ferry Terminal.
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
Historic Oak Bluffs home, short walk to town, beach, and harbor.

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

Oak Bluffs
When you stay at this vacation home in Oak Bluffs, you'll be by the sea, within a 10-minute walk of Martha's Vineyard Hospital Development and Oak Bluffs ...
Historic Oak Bluffs home, short walk to town, beach, and harbor.
Gorgeous Spacious Victorian Cape Code Beach View Retreat

Gorgeous Spacious Victorian Cape Code Beach View Retreat

Falmouth
When you stay at this vacation home in Falmouth, you'll be by the sea, a 1-minute drive from Cape Cod Beaches and 8 minutes from Woods Hole Ferry Terminal.
Gorgeous Spacious Victorian Cape Code Beach View Retreat
Charming coastal home with large yard, firepit, & grill - pool and beach access

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

Falmouth
With a stay at this vacation home in East Falmouth, you'll be by the sea, within a 5-minute drive of Cape Cod Beaches and Waquoit Bay National Estuarine Research ...
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

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

Falmouth
With a stay at this vacation home, you'll be centrally located in Falmouth, a 2-minute drive from Cape Cod Beaches and 11 minutes from Woods Hole Ferry ...
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

Coastal townhome with easy beach access, beach gear, balconies, grill, W/D, & AC

Mashpee
When you stay at this vacation home in Mashpee, you'll be by the sea, within a 5-minute drive of South Cape Beach and South Cape Beach State Park.
Coastal townhome with easy beach access, beach gear, balconies, grill, W/D, & AC
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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
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

Top trending hotels in Oak Bluffs

Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue, Oak Bluffs, MA
The price is AU$318 per night from 18 Apr to 19 Apr
AU$318
includes taxes & fees
18 Apr - 19 Apr
When you stay at Summercamp in Oak Bluffs, you'll be near the beach, just steps from Cottage Museum and 4 minutes by foot from Oak Bluffs Ferry Terminal.
Summercamp
Morgan Hotel

Morgan Hotel

2.5 out of 5
9 Healy Way, Oak Bluffs, MA
The price is AU$311 per night from 3 Apr to 4 Apr
AU$311
includes taxes & fees
3 Apr - 4 Apr
When you a stay at Morgan Hotel in Oak Bluffs, you'll be near the beach, just steps from Circuit Avenue and Ocean Park.
Morgan Hotel
The Attleboro House

The Attleboro House

2.5 out of 5
42 Lake Ave, Oak Bluffs, MA
When you a stay at The Attleboro House in Oak Bluffs, you'll be near the beach, just steps from Circuit Avenue and Cottage Museum.
The Attleboro House
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Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Oak Bluffs
The price is AU$862 per night from 1 Apr to 2 Apr
AU$862
includes taxes & fees
1 Apr - 2 Apr
With a stay at this apartment in Oak Bluffs, you'll be just steps from Oak Bluffs Ferry Terminal and Chappaquiddick Graveyard.
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Don't see what you're looking for?
See all available properties in Oak Bluffs
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.