25 Rooms

Value Season: $325-$695 per night

Summer: $395-$1000 per night

15 Rooms Summer Nightly Rates: $79 - $319

  Wonderfully affordable and superbly located in the heart of the village of Oak Bluffs on Martha's Vineyard Island , the Madison Inn is a charming seaside hotel just steps away from the gentle waters of Nantucket Sound. Our cozy, newly renovated and tastefully decorated guest rooms make a wonderful home away from home, a perfect location from which to explore and enjoy all of the fabled historic sites and beautiful vistas that make a stay on Martha's Vineyard such a memorable experience. Ideal for couples and families alike, the Madison Inn 's 14 well-appointed guest rooms include private bath, flat screen TV, in-room heat and AC, free wireless Internet service, and complimentary bottled water and snack baskets. Our unbeatable in-town location is convenient to all of the wonderful amenities that make Oak Bluffs the hub of summertime fun on Martha's Vineyard . The Madison Inn is an easy two-minute walk from picturesque Oak Bluffs Harbor , where all of the summer ferries dock, including those from Woods Hole, Falmouth , New Bedford , Hyannis and Nantucket . Just beyond our front doors are the historic Gingerbread Cottages, which are the original encampments of the first vacationers to Oak Bluffs.

2 Rooms/3 Apartments: 
Summer weekly rates: $650-$750, Summer nightly rates: $115-$160
Off season  weekly rates: $550 - $650, Off season nightly rates: $85-$135

Thorncroft Inn is a romantic, 14 room, first class, couples oriented, country inn situated in three restored buildings on 2½ acres of landscaped treed grounds, one block from the ocean. The inn has received a Four Diamond Award from the American Automobile Association every year since 1990.

The inn specializes in honeymoons, anniversaries, engagements, birthdays, elopements or any romantic getaway for which Martha’s Vineyard Island is the ideal setting. Our rooms are furnished with fine antiques and quality reproductions. Most of the inn’s bedrooms have working, wood burning fireplaces that are set up by our staff on a daily basis and match ready for guest convenience every day of the year.

Most rooms also have canopied beds; some have furnished balconies, private exterior entrances with private porches, two person whirlpools or private, in-room hot tubs. For absolute privacy, we have a stunning private cottage, complete with its own garage, two person whirlpool and large covered porch with two person hammock. Our concierge service is renowned and our experienced staff will provide you with inside information and assistance on every conceivable aspect of your Martha’s Vineyard Island vacation. Your romantic getaway will be truly first class at Thorncroft Inn.

All room prices include full country breakfast in our dining room or breakfast in bed. All rooms are air conditioned and have phone, color cable TV, high speed internet access and elegant bathrobes. There is ample free parking on premises.

14 Rooms Summer Nightly Rates: $175 - $600 Winter Nightly Rates: $200 - $425

The Dockside Inn is a family and small dog friendly Hotel built in 1989 in the Victorian style, with all the conveniences of a new modern facility, including 17 guest rooms and five apartment suites with kitchen facilities. Located within the Oak Bluffs Harbor front neighborhood, the Inn is close to everything including shopping, eateries, beaches, harbor side strolls, the movie theater, Flying Horses carousel, ice cream parlors, Island/Mainland ferries, Ocean Park and gazebo, Sunday night band concerts, nightclubs, bike / car / moped rentals, tour buses ... the list goes on and on! Going on a tour? Let us arrange one for you! Customer service is very important at the Dockside. Let us help you arrange that special getaway that will make your island visit unique. Most rooms have Queen beds, some two. One suite has a Jacuzzi tub, one a roof deck. All feature air conditioning, cable TV, in-room refrigerators, free WiFi, continental breakfast and are comfortably furnished for your vacation. We even have a lovely hot tub in our garden for a relaxing soak after a busy day.Our location near the Oak Bluffs Harbor front is a convenient base for all your island explorations!

22 Rooms Summer Nightly Rates: $165 - $360 Winter Nightly Rates: $120 - $325

8 Rooms & 2 Suites (one bedroom)
Room Nightly Rates: $99 - $269 
Suite Nightly Rates: $209 - $349
Rates subject to availability

Welcome to The Fallon located above the renowned l'etoile restaurant, in the heart of historic Edgartown. Eight guestrooms are unique, complete with all the amenities of a high end resort. Hardwood floors, cathedral ceilings, chandeliers, pedestal sinks, armoires and intricate crown molding are just a few of the characteristics that make our rooms irresistible. All of our rooms have private bathrooms with a shower, tub or Jacuzzi and offer king, queen or two twin beds. Our 2 suites have Harbor views and overstuffed chairs.Outside our front door is Water Street, one of Edgartown’s most sought after addresses. Specialty shops, galleries and gourmet restaurants await. The famous Edgartown Harbor is one block away. A short stroll brings you to Lighthouse Beach, one of five historic lighthouses on the Vineyard. Swim in the beautiful waters overlooking Chappaquiddick or simply relax with a good book and gourmet picnic basket. Rent a bike from The Fallon and discover the island at your leisure. The Fallon and l’etoile make the perfect setting for weddings, retreats and private parties. Book the entire inn and enjoy having all eight rooms available for friends and family. Your own vacation home right in the heart of Edgartown.