Downtown Oak Bluffs, Massachusetts

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

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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

THE PEQUOT HOTEL

19 PEQUOT AVE

Oak Bluffs, Massachusetts

Martha's Vineyard Resort

117 New York Ave

Oak Bluffs, Massachusetts

THE ISLAND INN

15 Island Inn Road

Oak Bluffs, Massachusetts

Hotel Tips

Other sources of noise can be opening and closing trash dumpsters and also during collection by garbage trucks. Another great question is if they have any renovation plans, or underway that could affect your ability to relax. Pack earplugs and eyeshades!

Always announce during booking if the trip is for a special event, anniversary or reunion. Group rates can be pre-negotiated and you may qualify for a lower cost and better upgrades for your stay. If you are the one setting up the event, always work directly with the front desk manager to make sure the best service is offered to your party.

Always tip staff when you feel the service was great and don't forget the housekeeping staff which you may never see. You should tip every day if you are staying multiple days as the staff may rotate out and miss the bounty at the end.

Things To Do

Oak Bluffs offers on-the-go dining when you visit your favorite food truck. Pick up some corn tortilla tacos with freshly made pico with a fresh squeeze of lemon to give your day a boost. Food trucks can offer a wide variety of niche ethnic blends.

Oak Bluffs keeps your pets fed, groomed, clothed and entertained with a wide assortment of ts.s available online and in-store. Does your dog need a bit of training? Check with us for great referrals to dog walkers, trainers and veterinarians who can work with your pets.

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.

Why Do You Love Downtown?

Kathleen Gerds

Looking forward to Ashland downtown. Theater and shopping here we come.

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!

Jackie

Have not been there but coming on a bus trip next weekend. Looking forward to shopping & sight seeing

Mary jo bos

My daughter moved to Talent this summer and I came to visit her for Christmas. She took me to the downtown Ashland area to shop. I love fall the shops and the friendliness .

Kathleen Zimmerman

I get the best of both worlds of big city living and upper peninsula awareness.

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