The Dockside Inn
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We are getting the Inn ready for another terrific summer on the Vineyard! To ensure that you have a safe, enjoyable experience while you're our guest, we have updated our policies regarding check-in and housekeeping. Please note, all of our rooms have private outside entrances, providing safe and private access to your room and allowing you to avoid the lobby or common areas of the hotel.

The Dockside Inn, located along the famously picturesque Oak Bluffs Harbor, is a boutique-style hotel which perfectly blends handsome, award-winning contemporary design with whimsical nautical decor and modern convenience. The Dockside Inn's 22 tastefully decorated rooms are perfect for couples, families, and wedding groups alike.

Our harbor-side location makes us the perfect place from which to explore and enjoy all of the fabled historic sites and beautiful vistas that make staying Martha's Vineyard a memorable experience.Our guests enjoy complimentary WiFi, beach gear, and ice, as well as access to our complimentary coffee and snack bar, hot tub, outdoor shower, and sun deck with lounge chairs.
Services
Take two hours to enjoy a classic Vineyard evening.
We'll head out in a luxury Oak Bluffs Land and Wharf transit vans-our first stop will be at the package store to choose your beverages.
Sit back and relax with your beverage of choice while your driver gives you an Island tour.
Arriving in Menemsha, get ready for an authentic Vineyard clam bake at Larsen's-lobster, clam chowder, and clam cakes; or the perfect lobster roll.
Then picnic on the beach at the best sunset watching spot on the Island!
Enjoy a historic tour of Martha's Vineyard with our sister company, Oak Bluffs Land and Wharf Co.
Martha's Vineyard is a small island with a big history.
From its timeless architecture, famous whaling ships and captains, to its pristine beaches and geologic marvels, there is a story behind it all.
Our local tour guides, in conjunction with the Martha's Vineyard Museum, know the history behind all the beauty.
Join us for a 2.5 hour narrated tour of all six towns, including a mid-tour stop at the beautiful cliffs of Aquinnah.
As part of your stay here at the Dockside, you'll have access to Loomis, our virtual concierge!
Loomis is ready to text with you and share his wealth of Martha's Vineyard knowledge.
Loomis is a living-breathing Islander who can answer any question you text him- from the practical, "Where do I catch the bus?" to the Islander insider, "Where's the best celebrity watching?" to the whimsical "How many sheep live on the Vineyard?"
Loomis can take you off the beaten path and ensure that your stay is memorable and just what you want.
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