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1,311 apartments
Adorable Cottage Walking Distance to Town and Beach
Oak Bluffs house
4 bedrooms / 1 bathroom / sleeps 7
Price per night from
$214
“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
Cozy townhouse w/ shared pool, tennis & great location close to the beach!
Oak Bluffs house
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$248
Charming house with lots of entertainment and gourmet kitchen!
Oak Bluffs house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$241
Price per night from
$287
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. 1 hour 5 minutes
Price per night from
$178
CLARO - New Contemporary Farmhouse Design, Multiple Living Areas, Screened Porch
Oak Bluffs house
3 bedrooms / 2 bathrooms / sleeps 7
Price per night from
$357
Ground-floor condo w/ shared pool & tennis courts, close to golfing & the beach!
Oak Bluffs house
1 bedroom / 2 bathrooms / sleeps 6
Price per night from
$204
Dog-friendly condo with shared pool & tennis courts - golf and beach nearby!
Oak Bluffs house
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$252
Responds fast! avg. 1 hour 22 minutes
Price per night from
$287
GOLLB - Waterfront, Private Beach, Gorgeous Water Views, Room AC, Wifi
Oak Bluffs house
3 bedrooms / 1 bathroom / sleeps 4
Price per night from
$214
Price per night from
$602
Lovely townhouse w/ private deck, shared pool & tennis - walk to the beach!
Oak Bluffs house
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$273
ALLER - Oak Bluffs 4 Bedroom Home, Walk to Town and Beach!
Oak Bluffs house
4 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$386
Price per night from
$717
Coastal getaway w/ shared outdoor pool & 3 tennis courts - 1/2 mile to the beach
Oak Bluffs house
1 bedroom / 2 bathrooms / sleeps 6
Price per night from
$212
ARMSA - Cozy Newly updated Seashore Cottage, East Chop Highlands Area, Farmers
Oak Bluffs house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$286
KEEFJ - Historic Waterfront Home Located just 1 Mile from Oak Bluffs Center, Pri
Oak Bluffs house
7 bedrooms / 3 bathrooms / sleeps 12
Price per night from
$3,193
Price per night from
$1,143
TOTHG - Adorable Updated Vineyard Cottage, Lovely Landscaped Yard, Central A/C,
Oak Bluffs house
3 bedrooms / 1 bathroom / sleeps 5
Price per night from
$300
Charming cottage with deck and playroom one mile from beach
Oak Bluffs house
4 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$164
Spacious Oak Bluffs Condo -Steps to Inkwell Beach
Oak Bluffs apartment
3 bedrooms / 2 bathrooms / sleeps 4
Responds fast! avg. 4 minutes
Price per night from
$343
“Gingerbread House”, water views, large porch!
Oak Bluffs cottage
4 bedrooms / 1 bathroom / sleeps 8
Price per night from
$459
LIJOY - Hidden Cove Summer Retreat, Newly Updated, Association Tennis Courts, B
Oak Bluffs house
4 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$357
Superb townhouse close to golfing & the beach - deck, tennis, & shared pool
Oak Bluffs house
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$231
Price per night from
$129
WHARG - Beautifully Decorated, Private Tennis Court, Walk to Town Center and Ink
Oak Bluffs house
3 bedrooms / 3 bathrooms / sleeps 6
Price per night from
$586
BRANF - Spacious Colonial with Contemporary Detailing in Fresh Pond Estates, Sc
Oak Bluffs house
4 bedrooms / 3 bathrooms / sleeps 8
Price per night from
$450
BURBR - Perfect Retreat for Large Families, 1.5 miles Oak Bluffs Town Center
Oak Bluffs house
6 bedrooms / 3 bathrooms / sleeps 13
Price per night from
$354
PETEV - Lovely Waterfront Home, Oak Bluffs, Gorgeous Water Views, Association T
Oak Bluffs house
4 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$351
DOHEM - East Chop Seaside Cottage, Large Porch, WiFi, Spectacular Views
Oak Bluffs house
3 bedrooms / 1 bathroom / sleeps 6
Price per night from
$529
PETEO - Beautiful Custom Built Home Overlooking Little Duarte Pond, Beautifully
Oak Bluffs house
4 bedrooms / 4 bathrooms / sleeps 8
Price per night from
$429
RUTHW - Lagoon Waterview, Central AC, 200 Yards to Lagoon, Swim and Kayak
Oak Bluffs house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$314
Solera Victorian charm, ocean view, steps to beach
Oak Bluffs cottage
4 bedrooms / 3 bathrooms / sleeps 9
Price per night from
$1,066
Price per night from
$500
SMEDM - Retreat to this Lovely Vacation Home with Main and Guest House, Central
Oak Bluffs house
7 bedrooms / 3 bathrooms / sleeps 10
Price per night from
$500
LEHNP - Beach Front East Chop Cottage, Spectacular Views, Perfect Getaway Cott
Oak Bluffs house
1 bedroom / 1 bathroom / sleeps 3
Price per night from
$179
Price per night from
$400
Viewing 38 of 1,311
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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