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650 Oak Bluffs Holiday Homes

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Compare Oak Bluffs holiday homes from 6 rental sites including HomeAway, TripAdvisor, Expedia 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

Save hundreds with a vacation home rental from Tripping.com and forget the hotel room. For the ultimate getaway, Oak Bluffs offers 650 affordable vacation rentals with a price to match your budget and accommodation needs. Prices in Oak Bluffs start at an average price of $492 a night with long-term rentals averaging $7928 a month.

These vacation rentals offer a range of amenities, so you’ll feel right at home. For those looking to stay in a corporate rental, 613 of Oak Bluffs’s rentals offer high speed WiFi Internet so you can easily keep in touch with your company or team. Go for a swim at one of the 29 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 609 vacation home rentals.

Traveling with your dog or cat? Choose from 90 pet-friendly rentals in Oak Bluffs that allow you to bring your extended family along.Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your pets. Many properties allow you to book directly online, so once you find that perfect vacation rental, you’ll be all set to go!

Search properties from 6 vacation rental sites in Oak Bluffs where the top providers in that area are HomeAway, TripAdvisor, and Expedia. There are 320 HomeAway rentals, 185 TripAdvisor short term rentals and 60 Expedia vacation rentals.