Downtown Oak Bluffs, Massachusetts

Discover shopping, dining, and accommodation in downtown Oak Bluffs.

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Hotels

Martha's Vineyard Resort

117 New York Ave

Oak Bluffs, Massachusetts

THE PEQUOT HOTEL

19 PEQUOT AVE

Oak Bluffs, Massachusetts

THE ISLAND INN

15 Island Inn Road

Oak Bluffs, Massachusetts

Hotel Tips

Bring an actual credit card to avoid deposits and pre-authorizations consuming money in your checking account which will reduce your available balance. Hotels that accept paper cash often ask for a hefty deposit to cover potential damages in your room leaving you scrambling to find an ATM.

Ask to be shown a room before you check-in which signals the front desk agent to show the best room available to sell it right away. This can put you in the best room available at that time and gives you the ability to check for cleanliness, smells and sounds before transacting with the hotel.

Avoid booking poolside for kids playing during the day and gatherings at night. Sound bounces off of the water and voices carry so ask for a room away from the pool either on the opposite side of the hotel or in higher floors.

Things To Do

Oak Bluffs brings the farming community under one marketplace to offer an assortment of locally grown fruit and vegetables. Traditionally, markets are restricted to anything grown so you can expect to see natural whole foods that are sure to please those working on their plant-based diets!

Oak Bluffs has a great collection of barber shops to choose from if you want to take a little off the top, get a clean shave or to trim your moustache or beard. Take a moment to consider buying some styling gel, beard oil or wax and always tip well.

Oak Bluffs hosts several events per year for your listening enjoyment but visit your piano shop to learn how to play and possibly purchase your grand, upright or digital piano. Don't forget the specialty work involved such as tuning and moving which are performed by skilled technicians.

Why Do You Love Downtown?

Megan H.

I love being able to browse a variety of my favorite restaurants and bars, all within easy walking distance of convenient parking. Enjoying local fare and live music downtown after a grilling day at the office makes every day feel like the weekend.

Darby

Visiting in July for the 1st time!

Angela Shields

I will be visiting Ashland for the first time this coming weekend! I have heard from numerous people what a great town it is and how much I will like it. Very excited to check it out and do some shopping!

Sophie Jacobson

I love downtown because it offers something for everyone!

Randy Swansen

We haven't been before, but we're looking forward to coming down next week!

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