We stayed at the Island Inn over Labor Day weekend (Aug. 30 - Sept. 1). It was a very adequate resort.
If you like tennis, then you will love this place. There are 3 high-quality courts on the property.
This isn't your normal hotel though...it's more like efficiency's (studio's) than hotel rooms. There is a mini-kitchen that includes two burners, a mini-fridge, coffee maker (yet, no coffee), microwave, and a full set of dishes / silverware / glasses. You can buy a 'k-cup' of coffee in the check-in house for $1. Seems like a rip-off to me, especially for the amount of money that you lay out for a room.
The shower comes equipped w/ 'Shampoo +' and 'Shower Gel' to cleanse yourself, and more than enough towels for 2.
There is also an iron & ironing board, but no hairdryer (luckily my girlfriend brought one!).
There is a restaurant located on-site called Lola's. It's a cajun-themed restaurant with VERY good food. Our waiter was sub-par, but maybe we realized that just because we are used to going to fine dining establishments in Boston.
One nice feature is that a local bike company (Anderson's) delivers bikes to the property and picks them up as well.
The grounds are beautifully maintained and the pool is quite nice. It is surrounded by flowers and plants to make it a more secluded area.
The rooms were very clean and the management very pleasant. They stored our bags after we checked out so we were able to enjoy the last hours of our time on the island.
Overall, I enjoyed the stay at this locale. While it wasn't what I expected (a regular hotel), it does offer a nice room away from the town center. I would highly recommend this resort if you want a room that is far enough away from the town center that you won't be bothered by noise, yet is close enough to walk / bike to Oak Bluffs, Edgartown, and all the beaches in between!
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