Book Holiday Homes in Oak Bluffs

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Featured Holiday Homes in Oak Bluffs

Cape Cod cottage

Cape Cod cottage

Mashpee
Stay at this vacation home in Mashpee. Enjoy free WiFi, a garden, and patios. Popular attractions Mashpee Wampanoag Indian Museum and Cahoon Museum of American ...
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
Book a stay at this beach vacation home in East Falmouth. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Woods Hole Ferry Terminal and Menauhant ...
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
Book a stay at this family-friendly vacation home in Chilmark. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Waskosim's Rock Reservation ...
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
Stay at this vacation home in Falmouth. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Woods Hole Ferry Terminal and Island Queen ...
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
Stay at this vacation home in Oak Bluffs. Enjoy free WiFi, a garden, and patios. Popular attractions Oak Bluffs Harbor and Oak Bluffs Town Beach are located ...
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
Stay at this vacation home in Falmouth. Enjoy a garden, an in-room coffeemaker, and housekeeping. Popular attractions Woods Hole Ferry Terminal and Wood Neck ...
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
Stay at this vacation home in East Falmouth. Enjoy a garden, tennis courts, and patios. Popular attractions Waquoit Bay National Estuarine Research Reserve and ...
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
Stay at this vacation home in Falmouth. Enjoy free WiFi, a garden, and patios. Our guests praise the helpful staff in our reviews. Popular attractions Woods ...
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
Stay at this vacation home in Mashpee. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Popponesset Beach and South Cape Beach State ...
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
NZ$296
Highest Price
NZ$354
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 NZ$354 per night from 27 Apr to 28 Apr
NZ$354
includes taxes & fees
27 Apr - 28 Apr
Stay at this 3.5-star beach hotel in Oak Bluffs. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the ...
Summercamp
Morgan Hotel

Morgan Hotel

2.5 out of 5
9 Healy Way, Oak Bluffs, MA
The price is NZ$326 per night from 1 May to 2 May
NZ$326
includes taxes & fees
1 May - 2 May
Stay at this hotel in Oak Bluffs. Enjoy free WiFi, concierge services, and cable TV channels. Popular attractions Circuit Avenue and Ocean Park are located ...
Morgan Hotel
Pequot Hotel

Pequot Hotel

3 out of 5
19 Pequot Avenue, Oak Bluffs, MA
The price is NZ$296 per night from 4 May to 5 May
NZ$296
includes taxes & fees
4 May - 5 May
Stay at this 3-star hotel in Oak Bluffs. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Pequot Hotel
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The Attleboro House

The Attleboro House

2.5 out of 5
42 Lake Ave, Oak Bluffs, MA
Stay at this hotel in Oak Bluffs. Enjoy free WiFi, housekeeping, and air conditioning. Popular attractions Cottage Museum and Circuit Avenue are located ...
The Attleboro House
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.