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Popular Oak Bluffs Vacation Rentals

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House Oak Bluffs
$314 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (24 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Vrbo
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Apartment Oak Bluffs
$154 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.7
"Outstanding" (46 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Vrbo
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House Oak Bluffs
$146 per night
House ∙ 6 guests ∙ 3 bedrooms
4.9
"Excellent" (66 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Vrbo
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House Oak Bluffs
$204 per night
House ∙ 3 guests ∙ 1 bedroom
4.9
"Excellent" (23 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Vrbo
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House Oak Bluffs
$261 per night
House ∙ 8 guests ∙ 3 bedrooms
4.9
"Excellent" (83 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Vrbo
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House Oak Bluffs
$394 per night
House ∙ 6 guests ∙ 4 bedrooms
5.0
"Excellent" (79 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Vrbo
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House Oak Bluffs
$180 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (57 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Vrbo
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Cottage Oak Bluffs
$194 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
4.9
"Excellent" (21 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Vrbo
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House Oak Bluffs
$272 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (35 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
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Vrbo
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Vacation rentals and apartments with air conditioning

Cottage Aircondition Oak Bluffs
$384 per night
Cottage ∙ 6 guests ∙ 2 bedrooms
4.3
"Very good" (51 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Aircondition
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Vrbo
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Cottage Aircondition Oak Bluffs
$288 per night
Cottage ∙ 4 guests ∙ 1 bedroom
4.7
"Outstanding" (54 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Aircondition
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Vrbo
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House Aircondition Oak Bluffs
$545 per night
House ∙ 6 guests ∙ 3 bedrooms
4.9
"Excellent" (22 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Aircondition
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Vrbo
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Vacation rentals with Wi-Fi

House Internet Oak Bluffs
$290 per night
House ∙ 6 guests ∙ 3 bedrooms
4.1
"Very good" (22 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Internet
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Vrbo
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Condo Internet Oak Bluffs
$356 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.9
"Excellent" (65 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Internet
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Vrbo
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House Internet Oak Bluffs
$245 per night
House ∙ 2 guests ∙ 1 bedroom
5.0
"Excellent" (28 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Internet
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Apartments and vacation rentals with a kitchen

House Kitchen Oak Bluffs
$389 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (84 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Kitchen
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Vrbo
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House Kitchen Oak Bluffs
$273 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (106 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Kitchen
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Vrbo
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House Kitchen Oak Bluffs
$484 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (32 ratings)
Oak Bluffs, Dukes County, Massachusetts, United States
Kitchen
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Vrbo
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Frequently Asked Questions

How much does a night in a vacation rental cost in Oak Bluffs on average?

You can book a vacation rental in Oak Bluffs for as little as $146 per night.

Are there lots vacation rental options to choose from in Oak Bluffs?

Currently, there are 428 vacation rentals available for you to compare and book.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Oak Bluffs Information

About Oak Bluffs

Oak Bluffs is a small town on the island of Martha’s Vineyard with a population of less than 5,000. The town is considered a romantic seaside vacation spot with beautiful beaches, pristine parks and historic attractions. If you are a big fan of fishing, Oak Bluffs boasts a super fishing pier where you will find your catch of the day. The island’s largest marina and destination for ferries from all along the coast, from Rhode Island to New York City, is at the center of it all. With spectacular accommodations, delicious restaurants and fun for two, or the whole family, Oak Bluffs is a small town with a big reason to visit.

Things to do in Oak Bluffs

Oak Bluffs is always hosting weekly or annual events so make sure to pick up a pamphlet when you arrive so you don’t miss out on their many art and musical events. Events such as the Harbor Festival or the famous Illumination Night held at the Tabernacle where you are bound to find music, dining, dancing and family fun. The town offers campground walking tours where a guide will take you through the historic district of the town and give you the unique background of the pastel colored cottages that line the streets of Oak Bluff. Other historic attractions include the Flying Horses carousel, the oldest working merry-go-round in the country, and the Cottage Museum filled with Victorian mansions and Gingerbread Cottages. Ocean Park is a huge hit with locals and visitors alike. Grab dinner and an ice cream at one of the charming seaside restaurants and then head over to the park for the “Fireworks at Ocean Park by the Sea” show. Music from Martha’s Vineyards’ local band serenades you from the gazebo and the fireworks start after the sun goes down. It is the best way to end summer.

Day trips from Oak Bluffs

Just 20 minutes down the coast, visit Edgartown and learn about its exciting whaling history. While you’re there explore Manuel F. Correllus State Forest, a Massachusetts state forest located on the island. The State Forest is great for a day of hiking and offers guided tours. Driving through the rural landscape of Chilmark you will find the fishing village of Menemsha. Martha’s Vineyard’s exclusivity will be put aside when you enter this authentic, seemingly timeless place where you will find local Sea Shacks and beautiful views. Cape Cod is just a ferry away with 15 towns to explore. It encompass seaside villages, fresh seafood, historic lighthouses, and ocean beaches. At the north most tip, Provincetown, offering numerous galleries, theaters, cabarets and nightclubs, marks the Pilgrims’ first anchorage in the New World.

Oak Bluffs accommodations

Originally named “Cottage City”, check Tripping.com for a variety of romantic Victorian seaside cottages on this summer resort that have been around for over a century. Multiple Bed and Breakfasts will always be a cozy place to stay along the coast and it will allow you to immerse yourself in the local culture. However, all of the nearby hotels and rentals have a small town charm and are walking distance from downtown.

Transportation in Oak Bluffs

On your trip to Oak Bluffs, you’ll most likely be taking a ferry, but when you arrive, you will be able to walk to everything downtown. If you’re looking to take a day trip around different parts of the island you can take it slow and bike through the small towns or use public transportation if you did not bring your car across the ferry with you. There are multiple bike rentals in Oak Bluff, as well as sightseeing tours. However you decide to explore, Oak Bluff is the perfect weekend getaway.

Popular Day Trips Near Oak Bluffs

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