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.






Lovely stay and the staff was friendly and helpful. Excellent location.
Reviewed on 17 December 2025

This is a quiet, comfortable, clean environment in walking distance to stores, the beach, restaurants, the post office, and the bus stop. There is parking in front of and a short distance walk from the hotel. The rooms are updated and offer what is needed for a relaxing stay.
Reviewed on 13 February 2026

Staff members, Alex and Amoy were wonderful. They were very accommodating and friendly.
Reviewed on 14 October 2025

We aren't sure where the previous reviews came from. But, our experience was not the same. The host communicated the entry information the week before we arrived and the directions were clear. We attempted to communicate with the host via text, email and through vrbo to ask if we could drop our luggage ...
Reviewed on 14 September 2025

This home is truly that, a welcoming escape nestled in the woods. It’s elevated beach-style furnishings feel hand-picked. We traveled with a 14 month old — the house had high-quality baby must haves, pack and play and high chair. We had the pleasure of a responsive host and caretaker. Close to trails, ...
Reviewed on 20 August 2022

This house was perfect for our getaway. Rebecca, the host, was extremely responsive and helpful during our trip. The house was as advertised. It was clean, well equipped, and the location was perfect as well
Reviewed on 10 November 2025

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.

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.

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 seafood restaurants.

Ocean Park is just one of the places to see in Oak Bluffs, so why not enjoy the other things to explore during your travels? Wander the area's waterfront or simply enjoy one of its wineries.

Enjoy an outing to Flying Horses Carousel during your stay in Oak Bluffs. Wander the beautiful beaches and waterfront in the 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.
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.
