4/5 - Good
Oak Bluffs is not as upscale as Edgartown, but has many very good restaurants and bars, a few nice stores, and a nice atmosphere. If you want more upscale, go to Edgartown. If you want more down to earth, Oak Bluffs is the choice for me.

Great location in Oak Bluffs - near a shuttle shop, lots of great shopping & restaurants. Room was nice size and room service was daily.
Reviewed on Nov 15, 2025

Great little hotel. All communication is done via texting. There is no one on site at this hotel. However it’s a great little hotel near restaurants and bars.
Reviewed on Nov 3, 2025

This was my second time staying at the island inn and no complaints here all good things. Very clean well kept, friendly staff and house keeping. I will definitely book again!
Reviewed on Oct 24, 2025

we were in a condo and it was GREAT....clean and well equipped. quiet street and nice people at the front desk. We will return.....
Reviewed on Nov 18, 2025

We had a truly wonderful stay at this resort. The hotel staff were incredibly professional, kind, and always ready to help. The rooms were cozy and spotlessly clean. The resort is located right by the ocean. Our room has a spacious balcony — perfect for enjoying the view. The surrounding area is ...
Reviewed on Nov 7, 2025

Friendly staff, spacious unit, clean and great location. We are looking forward to returning.
Reviewed on Nov 24, 2025

You can find out about the history of East Chop with a visit to East Chop Light. Stroll along the area's seaside, or simply savor its seafood restaurants.
If a restful vacation is part of your travel plans, Inkwell Beach might be the perfect place to seek out during your trip to Oak Bluffs. Stroll along this relaxing area's waterfront, or simply enjoy its wineries.
Explore the waterfront in Oak Bluffs with a trip to Oak Bluffs Harbor. Wander the area's beautiful beaches or simply enjoy one of its wineries.
If a restful vacation is part of your travel plans, Oak Bluffs Town Beach might be the perfect place to seek out during your trip to Oak Bluffs. Stroll along the waterfront or visit the shops in this relaxing area.
During your trip to Oak Bluffs, you can search for that perfect souvenir at Circuit Avenue. Wander the beaches and waterfront in this relaxing area.
Enjoy a round of golf in Oak Bluffs at Farm Neck Golf Club. Wander the area's waterfront or simply enjoy one of its wineries.
Oak Bluffs is not as upscale as Edgartown, but has many very good restaurants and bars, a few nice stores, and a nice atmosphere. If you want more upscale, go to Edgartown. If you want more down to earth, Oak Bluffs is the choice for me.
Awesome!
Great restaurants.
always eat at the Sand Bar and Nancy's. Frozen drinks from Donovan's Reef!
We come each year for the Grand Illumination and it never disappoints. This year we were very pleased with the close proximity to the ferry, Circuit Ave. & cottages.
There are more restaurants, shops, and ice cream options than you could possibly utilize on any given day. Everything is within walking distance including the beach and bike rentals.
