Book Holiday Homes in Oak Bluffs

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Featured Holiday Homes in Oak Bluffs

Charming 3 bed room with magnificent views & large deck

Charming 3 bed room with magnificent views & large deck

Barnstable MA
The price is AU$602 per night from 17 May to 18 May
AU$602
17 May - 18 May
includes taxes & fees
With a stay at this vacation home in Hyannis, you'll be within a 15-minute walk of Cape Cod Beaches and Hyannis Harbor.
Opens in a new windowCharming 3 bed room with magnificent views & large deck
Steps to the Beach in East Falmouth, PET FRIENDLY &  clubhouse heated pool.

Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.

East Falmouth MA
With a stay at this vacation home in East Falmouth, you'll be by the sea, a short 4-minute walk from Cape Cod Beaches and within 2 minutes by car from Waquoit ...
Opens in a new windowSteps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.
Private cottage nestled in center of the Vineyard

Private cottage nestled in center of the Vineyard

West Tisbury MA
When you stay at this vacation home in Vineyard Haven, you'll be near the beach, within a 5-minute drive of The Grey Barn and Farm and Polly Hill Arboretum.
Opens in a new windowPrivate cottage nestled in center of the Vineyard
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Lake House in Centerville with Private Water Access!

Lake House in Centerville with Private Water Access!

Barnstable MA
When you stay at this vacation home in Centerville, you'll be by the sea, within a 10-minute drive of Cape Cod Beaches and Main Street Hyannis.
Opens in a new windowLake House in Centerville with Private Water Access!
Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs

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

Oak Bluffs MA
With a stay at this vacation home, you'll be centrally located in Oak Bluffs, within a 5-minute drive of Inkwell Beach and Oak Bluffs Harbor.
Opens in a new windowCharming, cozy spacious home within 1 mile walking distance to Oak Bluffs
Family - friendly home 1.5 miles to Craigville Beach (Beach pass Inc.)

Family - friendly home 1.5 miles to Craigville Beach (Beach pass Inc.)

Barnstable MA
When you stay at this vacation home in Hyannis, you'll be by the sea, within a 5-minute drive of Cape Cod Beaches and Main Street Hyannis.
Opens in a new windowFamily - friendly home 1.5 miles to Craigville Beach (Beach pass Inc.)
3 Bed 2 Bath - Fully Renovated SS Granite kitchen walk to beach Falmouth heights

3 Bed 2 Bath - Fully Renovated SS Granite kitchen walk to beach Falmouth heights

Falmouth MA
With a stay at this vacation home, you'll be centrally located in East Falmouth, a 4-minute drive from Cape Cod Beaches and 13 minutes from Woods Hole Ferry ...
Opens in a new window3 Bed 2 Bath - Fully Renovated SS Granite kitchen walk to beach Falmouth heights
The Vienyard Haven Hideaway Apt

The Vienyard Haven Hideaway Apt

Tisbury MA
With a stay at this vacation home in Vineyard Haven, you'll be within a 15-minute drive of Inkwell Beach and Martha's Vineyard Museum.
Opens in a new windowThe Vienyard Haven Hideaway Apt
Bright & Open Central A/C Dog Friendly!

Bright & Open Central A/C Dog Friendly!

Barnstable MA
With a stay at this vacation home in Marstons Mills, you'll be by the sea, within a 15-minute drive of Main Street Hyannis and Olde Barnstable Fairgrounds Golf ...
Opens in a new windowBright & Open Central A/C Dog Friendly!
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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
1286 Holiday Homes
Lowest Price
AU$265
Highest Price
AU$602
Popular accommodation
Charming 3 bed room with magnificent views & large deck, Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool. , Private cottage nestled in center of the Vineyard, Lake House in Centerville with Private Water Access!, Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs, Family - friendly home 1.5 miles to Craigville Beach (Beach pass Inc.), 3 Bed 2 Bath - Fully Renovated SS Granite kitchen walk to beach Falmouth heights, The Vienyard Haven Hideaway Apt, Bright & Open Central A/C Dog Friendly!

Top trending hotels in Oak Bluffs

Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue Oak Bluffs MA
The price is AU$366 per night from 20 May to 21 May
AU$366
20 May - 21 May
includes taxes & fees
Located in Oak Bluffs, Summercamp is just steps from Cottage Museum and 4 minutes by foot from Oak Bluffs Ferry Terminal.
Opens in a new windowSummercamp
MV Surfside Hotel

MV Surfside Hotel

2.5 out of 5
7 Oak Bluffs Avenue Oak Bluffs MA
The price is AU$265 per night from 17 May to 18 May
AU$265
17 May - 18 May
includes taxes & fees
When you stay at MV Surfside Hotel in Oak Bluffs, you'll be in the historical district, just steps from Oak Bluffs Ferry Terminal and Oak Bluffs Fishing ...
Opens in a new windowMV Surfside Hotel
Morgan Hotel

Morgan Hotel

2.5 out of 5
9 Healy Way Oak Bluffs MA
The price is AU$303 per night from 17 May to 18 May
AU$303
17 May - 18 May
includes taxes & fees
When you stay at Morgan Hotel in Oak Bluffs, you'll be near the beach, within a 10-minute walk of Inkwell Beach and Circuit Avenue.
Opens in a new windowMorgan Hotel
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The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

2.5 out of 5
30 Island Inn Rd Oak Bluffs MA
With a stay at The Island Inn on Martha's Vineyard in Oak Bluffs, you'll be next to a golf course, within a 5-minute drive of Inkwell Beach and Joseph Sylvia ...
Opens in a new windowThe Island Inn on Martha's Vineyard
Don't see what you're looking for?
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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.

Top Picks

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