Martha's Vineyard.
Martha's Vineyard has a real chain problem — Faraway, Lark, Salt Hotels, and the Edgartown Collection between them operate most of the island's capacity. What remains truly independent is small: Hob Knob's century-old Gothic Revival on Upper Main, and a handful of historic Edgartown and Oak Bluffs inns. We include a few properties from the Edgartown Collection (3 properties, within our rule) with the owner group flagged.
The Charlotte Inn
An 1864 whaling captain's compound — 25 rooms, antique-furnished, Relais & Châteaux, adults-only.
Menemsha Inn
A 14-acre compound above Menemsha Harbor — family-run for decades, sunset porch, cottages.
The Christopher
Nine rooms in a white-clapboard historic, reworked with Art Deco geometric wallpapers and aqua tile.
The Hob Knob
A Gothic Revival inn on upper Main Street, nearly 100 years of hosting the Vineyard's quietest half.
Vineyard Square Hotel & Suites
A converted 1840s whaling-captain property — 35 rooms in the Edgartown historic district.
Dockside Inn
Twenty-two rooms on Oak Bluffs Harbor. Nautical without doing the too-much anchor thing.
The Edgartown Inn
A 1798 whaling captain's house where Hawthorne and Webster both stayed. Still operating. Still quiet.
Martha's Vineyard is a 100-square-mile island seven miles off Cape Cod, reached by the Steamship Authority ferry from Woods Hole. The hotel inventory has a real chain problem — Faraway, Lark, Salt Hotels, and the Edgartown Collection between them run most of the island's beds. What's truly independent is small, and that's what this page covers. Edgartown does most of the heavy lifting; Oak Bluffs, Chilmark, and Menemsha fill in.
What this looks like
Edgartown is the white-clapboard whaling-captain's town — Main Street is lined with 1830s houses with widow's walks. Oak Bluffs is the gingerbread-cottage town, lower-key and family-leaning. Up-island (Chilmark, Menemsha, Aquinnah) is rural — stone walls, hayfields, fishing harbors. The ferry takes 45 minutes from Woods Hole; the drive from New York to Woods Hole is about four and a half hours before you account for the boat.
The standouts
- The Hob Knob in Edgartown — a Gothic Revival inn on upper Main, nearly a century of innkeeping.
- The Christopher in Edgartown — nine rooms in a white-clapboard historic, reworked with Art Deco wallpaper.
- The Edgartown Inn — a 1798 whaling captain's house where Hawthorne and Webster both stayed. Still operating.
- The Charlotte Inn — an 1864 whaling-captain's compound, 25 antique-furnished rooms, Relais & Châteaux.
- Menemsha Inn in Chilmark — fourteen acres above Menemsha Harbor, family-run for decades, sunset porch.
- Dockside Inn in Oak Bluffs — twenty-two rooms on the harbor. Nautical without overdoing the anchors.
- Vineyard Square Hotel & Suites — a converted 1840s whaling-captain property, 35 rooms in the Edgartown historic district.
When to come / who it's for
The season runs Memorial Day through Columbus Day. July and August are peak — book in February. June and September are the savvy traveler's months: the same beaches without the ferry chaos. October still has the restaurants open and lower rates. The trip rewards either a long weekend (one town, one beach) or a full week (rent a car, do up-island properly).
Nearby
State Beach (the Jaws bridge, technically) and South Beach are the two big public beaches. The Black Dog in Vineyard Haven is the touristy stop; the Bite in Menemsha and Larsen's Fish Market are the real ones. The Aquinnah cliffs at the western tip are worth the drive. Cycle the Beach Road from Edgartown to Oak Bluffs — it's flat and scenic.