Downtown Oak Bluffs, Massachusetts

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

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Shop Downtown Discount Card

ShopDowntown.org Discount Card Program

The ShopDowntown.org Discount Card Program encourages local shopping by offering exclusive savings at participating downtown businesses. Shoppers can obtain a discount card by donating $20 or more to the American Cancer Society, unlocking deals of up to 15% off at local stores. The program supports small businesses, funds community health initiatives, and helps strengthen the local economy, making it a win-win for both merchants and consumers.

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Hotels

Martha's Vineyard Resort

117 New York Ave

Oak Bluffs, Massachusetts

THE ISLAND INN

15 Island Inn Road

Oak Bluffs, Massachusetts

THE PEQUOT HOTEL

19 PEQUOT AVE

Oak Bluffs, Massachusetts

Hotel Tips

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.

Upon check-in, slip the desk agent a tip and ask for the best room they can find at your current booked rate. Often times a quick $10 or $20 bill can go a long way towards the mood of the person who directly decides where you lay your head for the night.

Most hotel offer a complimentary breakfast bar or even a full cafe meal with your choice of a full menu. Keep in mind that some offer nothing at all so it is a good idea to pack a few packets of instant oatmeal for a quick and easy meal before you head out for the day.

Things To Do

Oak Bluffs is a great place to rent a bike and take it for a ride around downtown. There are many bike shops that sell bike and accessories as well as provide service and tuning on your ride. Don't forget your helmet and other protective gear such as reflective gear, headlight and horn.

Oak Bluffs gives several options to find the right piece of art as it takes time and a diligent effort to get just the right piece. Shopping for art downtown is the best way to locate your next purchase.

Oak Bluffs is the place to plan your wedding. You'll be spending a lot of time downtown as there are so many wonderful shops to find invitations, photographers, bakers, caterers and jewelers. Planning your wedding will be a breeze with so much support from local merchants to make a perfect and memorable day.

Why Do You Love Downtown?

Sharon Wright

I like the idea of downtown merchants being more visible and that they are locally owned and operated. It's great to see what's available downtown and I look forward to the discounts as well. Being a history buff, I love see the architecture as it was back in the day which is lost in modern buildings. Downtown is charming, inviting and quaint!

Tammy Cooper

Downtowns are so cute and has a very relaxed inviting vibe that puts a smile on my face. In addition, downtown was so clean. It was fun visiting the unique shops and boutiques and everyone was very friendly. Our stroll around Lithia Park was beautiful and so peaceful. It truly is a gem. Lastly, we ate at 4 or 5 different restaurants that had great food and great service.

Liisa Shunn

We love going downtown, because we like to support our local economy. The shops and restaurants we visit -- we have gotten to know the owners, so when our money is spent downtown, we know who benefits. Also? We live only a mile from downtown, so we walk or ride our bikes. No worries about a designated driver or looking for parking. We chose to live in Medford, so of course we want our money to stay in Medford, not going off to some corporate office of a chain store.

Laura

Very charming.

Angela Corrigan

Convenient, friendly. Stayed at Kermit inn.

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