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Cottages in Oak Bluffs and Holiday rentals - Holiday Lettings - Holiday Rentals Oak Bluffs

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516 Holiday homes

Holiday home letting

Oak Bluffs house

4 bedrooms • 2 bathrooms • sleeps 7

from £505 / night

£3,362 - £3,803 / week

1 / 5

Holiday home in Oak Bluffs

Oak Bluffs house

3 bedrooms • 2 bathrooms • sleeps 6

from £210 / night

£1,470 / week

1 / 22

Home letting in Oak Bluffs

Oak Bluffs house

7 bedrooms • 4 bathrooms • sleeps 12

from £728 / night

£5,091 - £8,724 / week

1 / 25

Holiday home in Oak Bluffs

Oak Bluffs house

4 bedrooms • 4 bathrooms • sleeps 8

from £520 / night

£3,636 / week

1 / 10

Apartment rental in Oak Bluffs with golf nearby

Oak Bluffs apartment

2 bedrooms • 1 bathroom • sleeps 5

“Favorite summer getaway!” This was my 4th summer staying at this property in Oak Bluffs. We love it!! The kitchen was renovated this year and is beauitful. We really enjoyed cooking in it, especially the fish we caught from our trip on "The Skipper" earlier that morning (which I highly recommend). The place is very spacious and accomodated our group very well. I especially love the balcony which overlooks Circuit ave. It's great for Bbqing, eating meals, and people watching! As always, we went to our favorite - "back door doughnuts" across the street several times during our stay. And the location cannot be beat! It's only a short walk to everything in Oak Bluffs (the ferry, the beach, bike rentals, restaurants, bars, and the colorful cottages in the Campground). I can't wait for next summer. Highly recommended!!

from £163 / night

£1,139 / week

1 / 32

Home rental in Oak Bluffs

Oak Bluffs house

2 bedrooms • 1 bathroom • sleeps 4

from £94 / night

£655 - £1,200 / week

1 / 10

Oak Bluffs holiday home let

Oak Bluffs house

3 bedrooms • 2 bathrooms • sleeps 6

from £241 / night

£1,682 / week

1 / 18

Oak Bluffs holiday cottage rental

Oak Bluffs cottage

4 bedrooms • 3 bathrooms • sleeps 9

from £708 / night

£4,956 / week

1 / 26

Holiday apartment in Oak Bluffs

Oak Bluffs apartment

3 bedrooms • 2 bathrooms • sleeps 4

from £387 / night

£2,710 / week

1 / 24

Holiday cottage in Oak Bluffs

Oak Bluffs cottage

4 bedrooms • 1 bathroom • sleeps 8

from £333 / night

£2,493 - £3,657 / week

1 / 12

Holiday home in Oak Bluffs

Oak Bluffs house

3 bedrooms • 3 bathrooms • sleeps 9

from £374 / night

£2,619 - £3,637 / week

1 / 24

Oak Bluffs holiday home rental

Oak Bluffs house

4 bedrooms • 4 bathrooms • sleeps 8

from £832 / night

£5,819 - £9,091 / week

1 / 30

Oak Bluffs holiday home rental

Oak Bluffs house

3 bedrooms • 2 bathrooms • sleeps 6

from £208 / night

£1,455 - £2,182 / week

1 / 12

Home rental in Oak Bluffs

Oak Bluffs house

7 bedrooms • 3 bathrooms • sleeps 14

from £395 / night

£2,764 - £6,182 / week

1 / 24

Holiday home in Oak Bluffs

Oak Bluffs house

3 bedrooms • 2 bathrooms • sleeps 9

from £167 / night

£1,164 - £2,182 / week

1 / 18

Holiday home in Oak Bluffs

Oak Bluffs house

4 bedrooms • 4 bathrooms • sleeps 8

from £312 / night

£2,182 - £4,073 / week

1 / 30

Oak Bluffs holiday home rental

Oak Bluffs house

6 bedrooms • 3 bathrooms • sleeps 12

from £416 / night

£2,910 - £13,746 / week

1 / 23

Holiday private room in Oak Bluffs

Oak Bluffs private room

1 bedroom • 1 bathroom • sleeps 2

from £250 / night

£1,749 / week

1 / 6

Home rental in Oak Bluffs

Oak Bluffs house

5 bedrooms • 5 bathrooms • sleeps 10

from £1,046 / night

£7,321 - £8,364 / week

1 / 32

Oak Bluffs holiday home rental

Oak Bluffs house

4 bedrooms • 2 bathrooms • sleeps 8

from £291 / night

£2,037 - £2,837 / week

1 / 15

Home rental in Oak Bluffs

Oak Bluffs house

5 bedrooms • 2 bathrooms • sleeps 9

from £260 / night

£1,819 - £3,200 / week

1 / 20

Holiday townhouse with golf nearby in Oak Bluffs

Oak Bluffs townhouse

3 bedrooms • 3 bathrooms • sleeps 12

from £329 / night

£2,302 / week

1 / 94

Oak Bluffs holiday home rental

Oak Bluffs house

3 bedrooms • 2 bathrooms • sleeps 9

from £658 / night

£4,600 - £5,437 / week

1 / 21

Holiday home in Oak Bluffs

Oak Bluffs house

3 bedrooms • 2 bathrooms • sleeps 8

from £304 / night

£2,161 / week

1 / 11

Home rental in Oak Bluffs

Oak Bluffs house

6 bedrooms • 3 bathrooms • sleeps 12

from £710 / night

£4,964 - £13,455 / week

1 / 24

Holiday home in Oak Bluffs

Oak Bluffs house

2 bedrooms • 1 bathroom • sleeps 5

from £260 / night

£1,819 / week

1 / 14

Oak Bluffs holiday home rental

Oak Bluffs house

2 bedrooms • 4 bathrooms • sleeps 12

from £624 / night

£4,364 - £11,637 / week

1 / 38

Oak Bluffs holiday home rental

Oak Bluffs house

2 bedrooms • 1 bathroom • sleeps 4

from £208 / night

£1,451 - £3,055 / week

1 / 13

Holiday home in Oak Bluffs

Oak Bluffs house

4 bedrooms • 3 bathrooms • sleeps 8

from £325 / night

£2,273 - £4,000 / week

1 / 20

Oak Bluffs holiday home rental

Oak Bluffs house

4 bedrooms • 3 bathrooms • sleeps 8

from £260 / night

£1,819 - £2,400 / week

1 / 21

Home rental in Oak Bluffs

Oak Bluffs house

3 bedrooms • 2 bathrooms • sleeps 6

from £301 / night

£2,110 - £3,782 / week

1 / 21

Home rental in Oak Bluffs with golf nearby

Oak Bluffs house

3 bedrooms • 2 bathrooms • sleeps 7

from £288 / night

£2,169 - £2,307 / week

1 / 13

Holiday home in Oak Bluffs

Oak Bluffs house

4 bedrooms • 2 bathrooms • sleeps 8

from £423 / night

£2,959 / week

1 / 5

Holiday home in Oak Bluffs

Oak Bluffs house

6 bedrooms • 3 bathrooms • sleeps 12

from £520 / night

£3,637 / week

1 / 20

Holiday home in Oak Bluffs

Oak Bluffs house

5 bedrooms • 3 bathrooms • sleeps 10

from £416 / night

£2,910 - £5,091 / week

1 / 33

Oak Bluffs holiday home rental

Oak Bluffs house

3 bedrooms • 2 bathrooms • sleeps 6

from £167 / night

£1,164 - £2,110 / week

1 / 18

Holiday home rental

Oak Bluffs house

4 bedrooms • 2 bathrooms • sleeps 8

from £187 / night

£1,310 - £3,491 / week

1 / 19

Oak Bluffs holiday home rental

Oak Bluffs house

4 bedrooms • 3 bathrooms • sleeps 9

from £400 / night

£2,800 - £6,728 / week

1 / 29

Holiday home in Oak Bluffs

Oak Bluffs house

3 bedrooms • 2 bathrooms • sleeps 6

from £291 / night

£2,037 - £2,182 / week

1 / 14

Oak Bluffs holiday home rental

Oak Bluffs house

6 bedrooms • 7 bathrooms • sleeps 14

from £1,808 / night

£12,644 - £13,234 / week

1 / 25

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Oak Bluffs holidays

The town of Oak Bluffs lies on the island of Martha’s Vineyard and is a popular tourist destination during the summer months, home to the largest marina on the island. Choose from over 900 Oak Bluffs holiday rentals and find your dream accommodation with Holiday Lettings.

About Oak Bluffs

The pretty Gingerbread Cottages here have appealed to holidayers for over 100 years, and it’s easy to see why this quaint and charming town remains such a popular destination. With ferries arriving at the Harbor from the mainland several times a day, families and couples come to Oak Bluffs for a relaxing break.

Beautiful beaches, rich history to explore and plenty of outdoor activities like golfing, fishing and hiking ensure that Oak Bluffs has everything you need for a great holiday. While you’re here, dine on delights such as fried seafood, blackened catfish and jambalaya. Wash it all down with a beer or root beer from the Offshore Ale Company, the island’s only brewery.

With around 203 sunny days a year, summer is definightly the warmest time to visit the town, but Oak Bluffs is just as beautiful during the Fall. Average summer temperatures are around 78 degrees Fahrenheit.

What to do

The beaches here are simply stunning, whether you head for Oak Bluffs Town Beach or relax on Joseph A. Sylvia State Beach. With two miles of golden sands, the calm waters and views of Cape Cod ensure this is a popular family spot that’s also good for windsurfing.

The marina here is a great spot for drinks and dining, with events like the Harbor Festival held here during the summer months. You’ll find the majority of stores, bars and restaurants on Circuit Avenue.

Don’t miss the chance to see the Flying Horses Carrousel, the oldest operating carrousel in the US, with hand-carved horses created in 1876.

There are plenty of outdoor activities here, too, with family fishing expeditions leaving from Oak Bluffs Dock and Farm Neck Golf Course with its 18-hole championship course and driving range. Pecoy Point Preserve is also nearby, with 14 acres of trails.

Top Oak Bluffs travel tips

Ferries arrive at the Harbor from the mainland from five different destinations in Massachusetts: Falmouth, North Kingstown, Woods Hole, New Bedford and Hyannis.

The best way to explore this compact town is definightly on foot, but there is a bus service, or you can rent a bike or moped in the town centre. There’s also a free pedicab service, with any tips and donations going to charity.

Beautiful beaches, family-friendly restaurants and outdoor activities continue to draw visitors to Oak Bluffs year after year.

Why not book a holiday rental with ocean views on Holiday Lettings today and come find out what Oak Bluffs has to offer?

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