Where to Stay
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.
9 Circuit Avenue Extension
Welcome to the Madison Inn, a charming seaside hotel located in the town of Oak Bluffs on the island of Martha’s Vineyard. We are just steps away from the blue-green waters of Nantucket Sound, and within easy walking distance from the Oak Bluffs harbor. Our unbeatable in-town location is convenient to historic sites including the Gingerbread Cottages, Flying Horses Carousel, Ocean Park, Union Chapel, and the East Chop Lighthouse. Oak Bluffs is a hub of summertime fun; cycling, kayaking, mopeding and swimming are some of the many activities available to visitors.
18 Kennebec Avenue
The Oak Bluffs Inn
The Oak Bluffs Inn is the perfect home base for your island vacation. The ten room Inn is walking distance to all Oak Bluffs has to offer with easy access for exploring the rest of beautiful Martha’s Vineyard.
64 Circuit Avenue
MV Surfside Motel
The Surfside Hotel is located in the heart of Oak Bluffs, Marthas Vineyard. “The Vineyard” is New England’s largest island and most beloved, consisting of six towns, endless pristine beaches, farm to table restaurants, and world class sightseeing amongst the islands natural beauty. Bicycling, beach combing, hiking, kayaking, paddle boarding, horse back riding, surfing, fishing, golf, tennis, farmers markets, local artists, musicians, theatre, and sailing are amongst a few of the local perks our island has to offer.
7 Oak Bluffs Avenue
From the decorative lattice that adorns our porches, to the cozy feel of classic cottage décor, this 32-room hotel exudes the warmth and charm of Martha's Vineyard tradition.
19 Pequot Avenue
A Bed + Breakfast Afloat
MS Resolute is a classic 40 ft Islander Cutter Sailboat docked at the picturesque Oak Bluffs Marina.Experience a unique boating adventure without ever leaving the dock. Enjoy romantic sunsets, be lulled to sleep by the gentle movement of the ocean, wake up to the sunrise, breathe in the fresh salt air and savor the sounds of the water lapping against the boat.
Formerly Samoset-on-the-Sound, The Beachfront Inn of Martha's Vineyard rests, resplendent in it's charm, directly across from the beach. Our time-honored cottage boasts an incredible sunrise and an unobstructed view of Nantucket Sound and the Cape Poge Lighthouse on the Island of Chappaquiddick.
65 Seaview Avenue
Brady's NESW B+B
Bradys NESW is a lovingly restored Victorian house that has been in the family since 1929. Just 500 feet from Nantucket Sound, it is perfectly situated for a quick morning dip, and just a walk from a long sandy beach.
10 Canonicus Avenue
Isabelle's Beach House
Isabelle’s Beach House is known for the panoramic ocean views from the sprawling front porch (as well as from some of their beach inspired guest rooms). Just minutes walking from the Martha’s Vineyard ferries, Oak Bluffs harbor and downtown Oak Bluffs, this sea side inn offers the most convenient location to restaurants, art galleries, and great shopping while still allowing inn guests to enjoy the relaxing water views and ocean breezes of Nantucket Sound.
83 Seaview Avenue
A Victorian Bed and Breakfast in the heart of Oak Bluffs in Marthas Vineyard. Steps to main street, harbor and the beach. Welcoming guests since 1880.
46 Narragansett Avenue
The Attleboro House has all of the conveniences of a modern hotel in the quaint atmosphere of a historic inn. Located among the famous Gingerbread Cottages and directly on the Oak Bluffs harbor, you’ll be in the perfect place for your visit to Martha’s Vineyard. Originally built in 1874, The Attleboro House was completely renovated in 2018. Relax on our wrap around porch to enjoy the bustling harbor and impressive views of the Nantucket Sound. Shops, restaurants and beaches are just a minutes’ walk away.
11 Lake Avenue
The Nashua House Hotel
Welcome to Shearer Cottage, family-owned and operated with pride since 1903. Shearer Cottage is nestled in a quiet, woodsy area in the Highlands of East Chop in Oak Bluffs on the Island of Martha's Vineyard. Our cottage overlooks the Baptist Temple Park, where religious services once took place. Our convenient location is a hop, skip and a jump to expansive beaches, picturesque bike trails and jogging paths, public golf courses and tennis courts, restaurants, shops and the many other attractions of Oak Bluffs.
4 Morgan Avenue
The Tivoli Inn is a lovely gingerbread house which has the island charm and exudes a clean and friendly atmosphere. Great location, walking distance to many fine restaurants and shops, night life, beach, hiking trails, public transportation and seasonal ferry terminals. Reasonable rates.
125 Circuit Avenue
East Chop Harborfront Apartments
The East Chop Harborfront Apartments are located on the East Chop shore of Oak Bluffs Harbor. A ten minute walk along the picturesque harbor to the town of Oak Bluffs, on the island of Martha’s Vineyard. Watch the ferries, boats and sunset from your private deck or take a walk along the sandy beach. This tranquil harborfront location is the ideal way to relax!
46 East Chop Drive
Part of the Oak Bluffs Victorian seaside resort tradition, this restored 19th century carpenter gothic "gingerbread" cottage houses just 12 guests. Titticut Follies is located one block from the beach and from downtown. There is a wonderful porch for rocking. The accommodations are casual and homey.
37 Narragansett Avenue