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838 Oak Bluffs Holiday Rentals

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Compare Oak Bluffs holiday rentals from 5 rental sites including HomeAway, TripAdvisor, WeNeedAVacation and more, from $25 a night.

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.

Vacation Rentals in Oak Bluffs

Looking for a vacation rental in Oak Bluffs? Tripping.com has 696 vacation rental homes available in Oak Bluffs. You'll find 5 studios, 84 1-bedroom, 93 2-bedroom and 514 rentals with 3 or more bedrooms ranging from $25 a night. For extra convenience, many of these vacation homes can be booked directly online.

The average price of a nightly rental in Oak Bluffs is $464 while the average price of a weekly rental is $3064. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Oak Bluffs home is $4550.

Wondering if you can bring your dog or cat along with you? There are 82 pet-friendly vacation rentals available in Oak Bluffs. In addition to accommodating pets, Oak Bluffs rentals offer a variety of amenities. In particular, 641 rentals have Internet and WiFi, 626 have TV and/or cable and 34 have a pool or hot tub.

Search properties from 5 vacation rental sites in Oak Bluffs where the top providers in that area are HomeAway, TripAdvisor, and WeNeedAVacation. There are 339 HomeAway rentals, 208 TripAdvisor short term rentals and 109 WeNeedAVacation vacation rentals.