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Oak Bluffs Vacation Rentals

(5 rentals)
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Charming Home On Farm Pond w/ Ocean View walk to Inkwell
Charming Home On Farm Pond w/ Ocean View walk to Inkwell

3 BR | 2 BA | Sleeps 6 | Quick View

$431

avg/night

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Key Amenities

  • Kid friendly

About this property

This warm, cozy home boasts 3 decks and a view of Farm Pond and Nantucket Sound. The front deck is perfect for reading a book and has access to the 2nd bedroom. The side deck has an electric awning that shades the area from the morning sun. The seating area and dining table allow you to enjoy a cup of ...

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Property Type

Oak Bluffs House

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Spacious Home - 1500 ft from Beach & Circuit Ave
Spacious Home - 1500 ft from Beach & Circuit Ave

4 BR | 2 BA | Sleeps 8 | Quick View

$643

avg/night

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Key Amenities

  • Kid friendly

About this property

4 bedrooms, 2 full bathrooms, sleeps 8, rocking chair porch, herb garden Newly renovated four bedroom, two full bathroom home with an inviting front porch, private backyard and footsteps to Circuit Avenue. The first level has an open floor plan with the following: a new fully equipped eat-in kitchen, ...

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Property Type

Oak Bluffs Cottage

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Vineyard Get Away
Vineyard Get Away

3 BR | 3 BA | Sleeps 6 | Quick View

Distance to beach: 3 miles to Inkwell, Joseph Silva State Beach

$557

avg/night

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Key Amenities

  • Rentals by owner

About this property

Located in the coveted Meadow View Farms development, you will enjoy this lovingly cared for, 3 Bedroom 2.5 Bath, Cape Style home. The desirable layout includes a first-floor master bedroom with a bathroom and two sizable bedrooms on the second floor. The open kitchen, living, and dining area is the perfect ...

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Property Type

Oak Bluffs House

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#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach!
#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach!

1 BR | 1.5 BA | Sleeps 2 | Quick View

last minute deal
LAST MINUTE DEAL 6/30 - 7/15: July 5-18, 5 night min, flexible arrival/departure dates & 10% off listed rates!

Distance to beach: 0.5 miles to Jetties Beach

$619

avg/night

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Key Amenities

  • Rentals by owner

About this property

Welcome to our #CozyBluffs home away from home in Oak Bluffs! Built in 2013 and nestled in a quaint Oak Bluffs residential neighborhood, our stand alone home features a large 1 bedroom suite, 1 & 1/2 baths, work loft, open concept living room and kitchen and a large enclosed back yard with outdoor ...

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Property Type

Oak Bluffs House

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DEAL
OB-POSH with Central A/C - Oak Bluffs
OB-POSH with Central A/C - Oak Bluffs

3 BR | 2 BA | Sleeps 6 | Quick View

2

$767

avg/night

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About this property

POSH... as in sumptuously comfortable, elegant, luxurious. caps...the only word to adequately describe the upscale high end furnishings, some one of a kind, many handcrafted. The interior is replete with such decor that it is a better vacation home for adults and older children, though none will be denied. ...

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Property Type

Oak Bluffs House

"The home was stunning"

n August 2023, my family and I had the pleasure of renting a property at 32 County Road, Oak Bluffs, MA, through Martha's Management. The home was stunning and provided an ideal setting for our family, ...

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Oak Bluffs Vacation Rentals
Nearby towns

Book a great Oak Bluffs vacation rental


Heading to Martha's Vineyard for a week during the summer should be on everyone's bucket list. While others may disagree, we think one area has the amenities and location that make booking an Oak Bluffs vacation rental the best option for your trip to the Vineyard.

It's an easy and direct ferry ride from Woods Hole or Hyannis to this island favorite where you'll find beaches, the famed cottages, and a surprisingly vibrant nightlife with everything from shop to bars to restaurants. Despite its happening main drag, Oak Bluffs is a great spot for family trips too and our selection of vacation houses is your best to to find the perfect rental for any size travel party. The Vineyard awaits!

Oak Bluffs, MA travel advice


The lively Circuit Ave area, Oak Bluff Harbor, and the beach are draws here. Plus, it's one of only two towns on the island that aren't dry (the other being Edgartown). Summer rentals in the Vineyard are hard enough to find. There's an active nightlife here and that makes it even more competitive to find and book a great vacation rental in Oak Bluffs. The fact is, there's alot more than just the so-called Gingerbread Cottages here so travelers best start their search for a house as soon as possible and likely during the winter months to ensure success.


Popular attractions and activities


Now, even though we just said there's more to Oak Bluffs than the cottages, they're still a popular and worthwhile spot! Their official name is Martha's Vineyard Camp Meeting Association (aka "The Campground") and they're part art and part history...totally worth a pic or two for the 'gram.

The Harbor is hard to miss because it's so picturesque, but some who stay in a vacation house in Oak Bluffs do overlook the family-friendly beach options here. Oak Bluffs Town is clean and has nice shallow waters for kiddos. Plus, it's handicap accessible. It connects diretly to "State Beach", which has the full name of Joseph Sylvia State Beach, which straddles Oak Bluffs and Edgartown.

Movie buffs and history buffs alike agree The Strand Theatre in Oak Bluffs is worth the price of admission. It's a piece of history that opened in 1915 and has weathered the test of time in part thanks to Martha's Vineyard Theater Foundation. The theater operates annually starting around June 15th and has a legit big screen so grab some popcorn and a seat!

Annual events


Annual Oak Bluffs Harbor Festival occurs annually in June. It's where the natives and seasonal travelers alike mix over seafood, music, and vendors from everywhere but especially some island favorites. There's no admission fee and there's family-appropriate entertainment, including the Annual Faerie Festival with some Celtic music.

If you're fortunate enough to lock down a vacation rental in Oak Bluffs and are there for the Oak Bluffs Fireworks and Band Concert, then count your blessings. The image of fireworks exploding over the harbor and the gazebo perched where the park and harbor meet is just breathtaking. Travelers and locals alike layout blankets and beach chairs and enjoy the show. This is a no-brainer if you're on the Vineyard when it happens, get there by 7pm the latest.

Oak Bluffs is a great spot for off-season travel as well. Specifically the annual tree lighting event to kick off holiday season in its Post Office Square. What a way to stay warm during the winter holidays!

Great restaurants and food in Oak Bluffs


First, let's get the obvious out of the way: there is no shortage of options to eat and drink in Oak Bluffs. The striking views from the Lookout Tavern are well known so if you want a view that makes the ocean look endless to go with your seafood, then you're easy...just be sure to get there early.

What's perhaps harder is figuring out which local spot has the best fried seafood. Many say it's Nancy's, which is a very family-friendly restaurant on Lake Ave and is uber-popular.

A stone's throw from Nancy's is Fishbones Bar & Grille and its a nifty waterside patio. Enjoy its cool atmosphere and delicious bites to boot -- we hear their fish tacos and clam chowder are quite tasty.

No vacation on the Vineyard is complete without some ice cream and Oak Bluffs has you covered. There are literally a dozen options but for our money it's either Ben & Bill's or Smitty's Homemade. Both have...you know...great, vacation-worthy ice cream.


Oak Bluffs vacation rentals on Cape Cod Vacation Rentals


Booking the right vacation rental is a critical part of having a great trip to Oak Bluffs. We have the best selection right here on CapeCodVacationRentals.com to help you save and have it all. We're happy to help you find the house that's ideal for your trip. So get started and contact the rental you want right away...you're one step closer to the Vineyard!