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618 apartments
Adorable Cottage Walking Distance to Town and Beach
Oak Bluffs house
4 bedrooms / 1 bathroom / sleeps 7
Price per night from
$214
In-Town Historic Property on Martha's Vineyard
Oak Bluffs apartment
2 bedrooms / 1 bathroom / sleeps 5
“One of Oak Bluffs best kept secrets!” My family and I have been vineyarders for decades, and have been accustomed to rental property's away from the busy streets of downtown Oak Bluffs. Needless, to say we weren't optomistic about what to expect. However, everything from the ease of reservation, kindness of staff, attentiveness to our concerns, and extreme hospitality made this a wonderful and memorable stay. The concerns about the noise are real, but wasn't an issue for us and I'm fairly noise sensitive. The location is beyond ideal, the property beautifully decorated, cleaned and maintained, and the proximity issue was actually quite pleasant after all our years of visiting the island. As a side note Larry's hospitality is beyond measure for so many reasons I can't name them all here. The bottom line...I would recommend this property to anyone and everyone, definitely a winner.
Responds fast! avg. 3 hours 49 minutes
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$225
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$276
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$717
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$143
“A memorable week at the Vineyard” We had a most enjoyable week - very comfortable accommodation. Everything went smoothly for our son's wedding, even the weather was kind!
Price per night from
$1,000
Responds fast! avg. 1 hour 27 minutes
Price per night from
$334
Lovely Oak Bluffs home one mile from town and beach
Oak Bluffs house
3 bedrooms / 3 bathrooms / sleeps 9
Price per night from
$514
Price per night from
$1,143
Solera Victorian charm, ocean view, steps to beach
Oak Bluffs cottage
4 bedrooms / 3 bathrooms / sleeps 9
Price per night from
$1,011
Breezy Oak Bluffs Condo - Steps to Inkwell Beach!
Oak Bluffs apartment
3 bedrooms / 2 bathrooms / sleeps 4
Responds fast! avg. 1 hour 59 minutes
Price per night from
$380
“Gingerbread House”, water views, large porch!
Oak Bluffs cottage
4 bedrooms / 1 bathroom / sleeps 8
Price per night from
$449
Five bedroom, in-town, Oak Bluffs home with water views!
Oak Bluffs house
5 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$1,314
Beautiful Oak Bluffs Home with Wonderful Waterviews
Oak Bluffs house
5 bedrooms / 5 bathrooms / sleeps 10
Price per night from
$1,438
Cape Style Home near Lagoon Pond- short walk to Lagoon Beach
Oak Bluffs house
4 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$371
Price per night from
$543
OAK BLUFFS VICTORIAN ONE BLOCK FROM BEACH, TWO BLOCKS FROM TOWN!
Oak Bluffs house
6 bedrooms / 3 bathrooms / sleeps 12
“We had a restful time and we laughed alot - the porch was great!” The house was very nice - we had fun laughing and playing games. Proximity to the beach and town was great and all within walking distance. The layout was nice except the difficult steep stairs near kitchen - overall great time.
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$1,271
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$389
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$571
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$500
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$407
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$904
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$229
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$1,143
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$457
Newly Renovated 2 Bedroom Oak Bluffs House within Walking Distance to Town
Oak Bluffs house
2 bedrooms / 1 bathroom / sleeps 5
Price per night from
$286
Beautiful four bedroom house in the Farm Neck area of Oak Bluffs
Oak Bluffs house
4 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$643
Lovely three bedroom home located in the Hidden Cove area of Oak Bluffs
Oak Bluffs house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$286
Gracious five bedroom in-town Oak Bluffs victorian
Oak Bluffs house
5 bedrooms / 2 bathrooms / sleeps 9
Price per night from
$357
Clean, comfortable ranch with lots of amenities
Oak Bluffs house
3 bedrooms / 2 bathrooms / sleeps 7
Price per night from
$329
Spectacular Martha's Vineyard Island Home!
Oak Bluffs townhouse
3 bedrooms / 3 bathrooms / sleeps 12
Responds fast! avg. 2 hours 36 minutes
Price per night from
$440
Charming 4 bedroom home in the east chop neighborhood of Oak Bluffs
Oak Bluffs house
4 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$556
Beautiful Four Bedroom Home Walking Distance to Downtown Oak Bluffs
Oak Bluffs house
4 bedrooms / 3 bathrooms / sleeps 9
Price per night from
$525
Beautiful Main & Guest house short walk to Lagoon Pond
Oak Bluffs house
5 bedrooms / 3 bathrooms / sleeps 10
Price per night from
$571
Adorable Oak Bluffs Cottage Walking Distance to Town
Oak Bluffs house
2 bedrooms / 1 bathroom / sleeps 4
Price per night from
$285
Enjoy the charm of a Vineyard cottage with all the amenities of today
Oak Bluffs house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$257
ENJOY WATERVIEWS OF SENGENKONTACKET POND FROM THE WONDERFUL DECK
Oak Bluffs house
4 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$257
Beautiful Oak Bluffs home on Lagoon Pond with Pool!
Oak Bluffs house
4 bedrooms / 4 bathrooms / sleeps 10
Price per night from
$571
Viewing 38 of 618
rentals in Oak Bluffs
About Oak Bluffs
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 vacation rentals and find your dream accommodation with FlipKey.
About Oak Bluffs
The pretty Gingerbread Cottages here have appealed to vacationers 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 vacation. 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 definitely 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 Carousel, the oldest operating carousel 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 definitely on foot, but there is a bus service, or you can rent a bike or moped in the town center. 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 vacation rental with ocean views on FlipKey today and come find out what Oak Bluffs has to offer?
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