Step into the charm of Oak Bluffs, where coastal beauty meets laid-back island vibes. Whether you're waking up to ocean breezes, strolling past colorful cottages, or savoring fresh seafood by the harbor, every moment here feels like a postcard come to life.
Relax in comfort, explore with ease, and create lasting memories in a place that feels like home—but better.
Your getaway starts here. Where will Oak Bluffs take you?
Local Highlights
Oak Bluffs is walkable, photogenic, and packed with charm. Whether you're chasing sunsets at East Chop, swimming at Inkwell Beach, or grabbing ice cream after a carousel ride, every moment feels like a postcard.
Amenities
Your comfort is our priority. We’ve thoughtfully designed every detail of your stay to ensure a seamless and relaxing experience. From plush bedding and a fully equipped kitchen to high‑speed Wi‑Fi and cozy outdoor spaces, our amenities are tailored to make you feel right at home.
Book Your Stay
Whether you're craving adventure, tranquility, or a little bit of both, we’ve created the ideal space for you to unwind, explore, and feel right at home.
Weeks fill up fast—secure your dream vacation today and let your Martha’s Vineyard journey begin!
Guest Reviews
“Our time in this lovely home was just amazing. The home was perfect for our mother & daughter getaway. From the perfect location close to everything in town. To cleanliness and very comfortable space made for small or big groups. Maja was an amazing host and helped us with anything that we needed. We will definitely be back for sure!”
- Christiana
“My family was already excited to stay at The Retreat at Towanticut, but our experience far exceeded our high expectations! The homeowner was an absolute joy to deal with as well. She was always accessible and she wanted feedback on how to make our stay even better. This house has it all - a quiet neighborhood that is walking distance from downtown Oak Bluffs, extremely clean and newly renovated, beautifully decorated, brand-new appliances, smart TVs in every room, a hot tub, lawn toys and everything you would want or need for the beach, all while being reasonably priced. This house was our favorite rental - and we have been coming to The Vineyard regularly since 2012. We can't wait to come back here!”
- Eddie
“My family and I stayed a here for a couple days in July. We had a fabulous time and the rental was beautiful and nicely decorated. We felt at home and it was so cozy. Our host was wonderful communicating with me and helpful with recommendations in the area. The rental was within walking distance to the beach and town of Oak Bluffs which is a positive because sometimes it’s hard to find parking. We loved it and hope to be back someday!”
- Julie
“The house is wonderfully spacious and well equipped. They have plenty of amenities from smart TVs, in home w/d, spacious deck, hot tub & beach supplies (chairs,wagon,games) we were a group of 7 women and had plenty of space in the house without feeling on top of each other. It can be difficult to convince adults to stay in a bunk bed but the mattresses were amazing! The hosts are very responsive and came quickly when we requested more towels. There's space for a car but we did not rent one, very easy to walk into Oak Bluffs town area!”
- Kennedi