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Price $10 - $1000+

1,924 Oak Bluffs Holiday Rentals, Houses & Apartments

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Oak Bluffs holiday rentals from 9 rental sites including HomeAway, TripAdvisor, WeNeedAVacation, and more, ranging from $25 to $14142 a night. 
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    Information about Oak Bluffs

    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

    Find the best Oak Bluffs vacation rentals with Tripping.com. Choose from 1,925 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $14142 a night.

    Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 1,601 of homes in Oak Bluffs offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 190 rentals with pool or jacuzzi, or relax with the family in one of the 1,798 homes with cable TV.

    For all those dog lovers and cat lovers, Oak Bluffs offers 293 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

    Search properties from 9 rental sites in Oak Bluffs where the top providers in that area are HomeAway, TripAdvisor, and WeNeedAVacation. There are 835 HomeAway rentals, 503 TripAdvisor short term rentals and 404 WeNeedAVacation vacation rentals.