The short answer
| If you want | Stay in |
|---|---|
| To walk to restaurants, shops and the harbor | Edgartown village, Oak Bluffs or Vineyard Haven |
| The easiest ferry days | Vineyard Haven (year round) or Oak Bluffs (in season) |
| Kids, calm beaches and ice cream | Oak Bluffs and the Edgartown end of State Beach |
| Ocean surf | Katama in Edgartown, near South Beach, or Chilmark’s south shore |
| Privacy, views and quiet | Chilmark, Aquinnah, Chappaquiddick or West Tisbury |
| Sunsets | Menemsha in Chilmark, Aquinnah, or the Lagoon in Vineyard Haven |
| To be central to everything | Vineyard Haven or West Tisbury |
Down-island: the harbor towns
The three towns where the ferries land are walkable, lively in summer and connected by bike paths and free buses.
- Edgartown village: white captains’ houses, the harbor and Main Street. The most polished corner of the island. Edgartown rentals.
- Katama: south of Edgartown village, with bigger lots, newer homes and the bike path to South Beach.
- Chappaquiddick: across Edgartown harbor on the Chappy Ferry. Quiet roads, wild beaches, no shops.
- Oak Bluffs: gingerbread cottages, the carousel, Circuit Avenue and three seasonal ferry lines in town. Oak Bluffs rentals.
- East Chop: the bluffs above Oak Bluffs harbor, with a lighthouse and big Sound views.
- Vineyard Haven: the year-round ferry, Main Street and wooden boats. Vineyard Haven rentals.
- West Chop and Lake Tashmoo: leafy, quiet and on the water, minutes from Vineyard Haven.
Up-island: farms, ponds and the cliffs
The three rural towns trade walk-to-dinner for space, privacy and some of New England’s best beaches, several of them for residents and renters only. You will want a car.
- West Tisbury: farm stands, the farmers market and Lambert’s Cove Beach. West Tisbury rentals.
- Chilmark: stone walls, ocean views, Lucy Vincent Beach and Menemsha’s sunsets. Chilmark rentals.
- Menemsha: Chilmark’s fishing village, for seafood on the dock and the island’s most famous sunset.
- Aquinnah: the clay cliffs, the Gay Head Lighthouse and the end-of-the-island quiet. Aquinnah rentals.
Lucy Vincent and Squibnocket (Chilmark), Lambert’s Cove (West Tisbury) and Philbin (Aquinnah) are for residents and renters in summer. A copy of your lease gets you a pass. See our beach guide.
Matching the house to the group
Most families find a three-bedroom or four-bedroom home is the sweet spot. Two families together usually want five bedrooms, and reunions need six or more. Bringing the dog? See our pet-friendly homes.
Not sure? Call us at 508-627-0476. We know every one of our homes and will match you in a few minutes.
Questions we hear
What is the best town to stay in on Martha’s Vineyard?
It depends on your trip. Edgartown, Oak Bluffs and Vineyard Haven are walkable harbor towns with restaurants and ferries; Chilmark, West Tisbury and Aquinnah are rural, private and close to the renter-only beaches.
Where should first-time visitors stay on Martha’s Vineyard?
Most first-timers love Edgartown or Oak Bluffs: you can walk to dinner, bike to the beach and take the free bus to the rest of the island without needing a car.
Is it better to stay up-island or down-island?
Down-island (Edgartown, Oak Bluffs, Vineyard Haven) for convenience, nightlife and walking; up-island (West Tisbury, Chilmark, Aquinnah) for space, views, quiet and beaches limited to residents and renters.
By Patrick McCarthy, Rent Martha’s Vineyard, Oak Bluffs. Updated October 2026. Hours, seasons and rules change: check with each business or town before you go.