Six distinct island towns connected by harbors, beaches, farms, historic neighborhoods, seasonal restaurants, bike routes, buses, and ferries—but no bridge to the mainland.
Photo: Don Ramey Logan · CC BY-SA 4.0 · Cropped and resized
Quick Picks: Best Hotels in Martha's Vineyard, Massachusetts
Best for Families
Best Overall
Best Boutique / Unique Stay
Best Value
Best Luxury
The island’s most polished town — white-clapboard houses, a historic harbor, and the best concentration of dining and boutiques. South Beach (Katama) is a short bike ride away. The most popular base for first-time visitors.
The Vineyard’s most energetic town — gingerbread cottages, Circuit Avenue, and the island’s best nightlife. Walkable, fun, and ideal for younger visitors or anyone who wants activity in the evenings.
The main ferry port and most lived-in town on the island — independent shops, reliable restaurants, and a quieter, more practical base. Best for convenience and year-round access.
Rolling farmland, stone walls, and the fishing village of Menemsha — known for lobster dinners on the beach at sunset. Quiet, beautiful, and removed from the main towns. A car is essential.
The island’s western tip — striking clay cliffs, a historic lighthouse, and long, uncrowded beaches. Remote and culturally significant, with deep ties to the Wampanoag Tribe.
A quiet inland area defined by farms, markets, and conservation land — home to the West Tisbury Farmers Market and Long Point Beach. Best for a slower, more local experience.
Getaway Unpacked may earn a commission when you book through selected links, at no additional cost to you. Recommendations remain independently curated.
Classic Luxury · Boutique · Refined
A Relais & Châteaux inn in the heart of Edgartown — antiques, garden courtyards, and a quiet, traditional atmosphere. One of the most refined stays on the island.
Rates vary substantially by date, season, room type, and stay rules
Historic · Harbor Views · Resort Feel
The island’s iconic waterfront hotel — wraparound porch, lighthouse views, and a full-service setup steps from town. Classic Vineyard stay with strong location.
Rates vary substantially by date, season, room type, and stay rules
Resort · Family-Friendly · Beachfront
A full-service resort on South Beach with suites, cottages, pools, and direct beach access. The best option on the island for families.
Rates vary substantially by date, season, room type, and stay rules
Modern · Design-Forward · Social
A reimagined historic inn turned into a multi-building hotel campus — lively, stylish, and one of the most exciting recent openings on the island.
Rates vary substantially by date, season, room type, and stay rules
Modern Boutique · Central · Design
A bright, contemporary inn with a fresh coastal aesthetic — steps from Main Street and a strong alternative to more traditional Edgartown stays.
Boutique · Romantic · Intimate
A small, polished inn on Main Street with just 17 rooms — known for excellent breakfast, attentive service, and a quiet, romantic feel.
Rates vary substantially by date, season, room type, and stay rules
Romantic · Secluded · Scenic
A nine-room inn overlooking Menemsha harbor — gardens, a strong restaurant, and one of the most atmospheric settings on the island.
Rates vary substantially by date, season, room type, and stay rules
Practical · Year-Round · Full-Service
A reliable, centrally located hotel with access to a full health club and pool — one of the best options for year-round stays.
Rates vary substantially by date, season, room type, and stay rules
Modern Farmhouse · Boutique · Relaxed
A smaller Lark Hotels property with a clean, farmhouse-inspired design — breakfast included and an easy, comfortable base in town.
Rates vary substantially by date, season, room type, and stay rules
Beachfront · Boutique · Historic
A small, character-filled inn directly across from Inkwell Beach — simple, warm, and one of the best true beachfront locations on the island.
Rates vary substantially by date, season, room type, and stay rules
Harborfront · Central · Resort Feel
A well-located waterfront hotel in the heart of Edgartown — large property, heated pool overlooking the harbor, and walkable to shops, restaurants, and the ferry. Best for travelers who prioritize location and views over boutique style.
Playful · Social · Value
A colorful, camp-inspired hotel overlooking the harbor — lively atmosphere, great porch, and strong value for the location.
Rates vary substantially by date, season, room type, and stay rules
Classic · Friendly · Central
A well-run Victorian inn near the beach and Circuit Avenue — simple, reliable, and one of the best-value options in town.
Rates vary substantially by date, season, room type, and stay rules
The island's most celebrated restaurant: upstairs is white tablecloths and twinkle lights in an 18th-century sea captain's home; downstairs is a glam-rock speakeasy with neon and leopard print. The wok-fired two-pound lobster is essential.
Learn MoreA no-frills seafood shack on the Menemsha docks serving ultra-fresh lobster rolls, chowder, and shellfish—best enjoyed picnic-style at sunset overlooking the harbor. Take your order to Menemsha Beach to watch the sunset.
Learn MoreWest Tisbury's farm-to-table anchor — locally sourced, seasonally driven, rustically elegant. Pan-roasted island fish, house-made pasta, and the most local cooking on the island. Book ahead.
Learn MoreEdgartown's most charming restaurant — a husband-and-wife team, a garden patio, creative seasonal New American with French and Italian touches. The most reliably excellent dinner in town.
Learn MoreThe island's most iconic institution since 1971 — a waterfront tavern in Vineyard Haven with a legendary brunch, a loyal local following, and merchandise that has become a cultural touchstone of the American summer.
Learn MoreEdgartown's classic chrome-stools diner — linguiça, egg, and cheese breakfast sandwiches on a flat-top griddle, walk-in only, cash preferred. The most essential Vineyard breakfast.
Learn MoreA year-round Edgartown pub serving lunch and dinner daily, with seafood, sandwiches, pub standards, takeout, sports, and a separate Back Bar that hosts live music and late-night events.
Learn MoreTwo different beach experiences: open-ocean South Beach near Edgartown and the protected landscape of Long Point Wildlife Refuge in West Tisbury. Surf, parking, reservations, access points, and seasonal rules require separate checks.
Learn MoreShared-use paths connect many popular down-island routes, but the network has important gaps and is not a fully protected island loop. Plan distance, road exposure, traffic, weather, and return transportation before renting.
Learn MoreBuild a Menemsha sunset meal from one of the fishing village’s seafood counters, then walk to the beach. Availability, waits, parking, menus, and weather change, so arrive with alternatives rather than a fixed order or budget.
Learn MoreWalk the historic campground’s colorful cottages and Trinity Park, then pair the visit with the seasonal Flying Horses Carousel. The neighborhood is residential, so explore quietly and photograph respectfully.
Learn MoreA small ferry from Edgartown reaches Chappaquiddick, where Mytoi, Cape Poge, and Wasque require deliberate transportation and access planning. Vehicle lines, protected shorebirds, erosion, currents, and permits can change the day.
Learn MoreA dramatic up-island landscape and culturally important place within the homeland of the Wampanoag Tribe of Gay Head (Aquinnah). Use designated overlooks and paths, respect restricted cliff areas, and check lighthouse access separately.
Learn MoreLanguage
English.
Currency
US Dollar (USD).
Getting There
The Steamship Authority operates the only vehicle ferry from Woods Hole; vehicle travel requires a reservation, while traditional-ferry walk-on passengers generally buy tickets at the terminal. Other passenger ferries and flights are seasonal. Confirm schedule, mainland parking, arrival town, and connections directly.
Getting Around
VTA buses connect island towns, and bicycles, taxis, rideshares, and rental vehicles fill different needs. Bus routes and fares change seasonally. The shared-use path network has gaps, and bringing a vehicle requires reserved ferry space.
Time Zone
Eastern Time: EST in winter and EDT during daylight saving time.
Best Time
July and August have the fullest calendar and highest demand. June and September can be calmer while retaining many services. Late fall through spring is quiet and many businesses reduce hours or close seasonally.
Visa
Domestic US destination; identification requirements depend on the traveler and mode of transportation.
FAQ
Edgartown offers a polished, walkable center with strong dining. Oak Bluffs is lively, colorful, and convenient for summer ferry arrivals. Vineyard Haven is the practical year-round port. Chilmark, Menemsha, Aquinnah, and West Tisbury provide quieter rural or coastal settings but require more transportation planning.
Three nights works for two or three down-island towns and a beach day. Four or five nights allows an up-island outing, Chappaquiddick or a nature reserve, and flexibility for ferry or beach weather. A week supports a slower, town-by-town visit.
The Steamship Authority operates the only vehicle ferry between Woods Hole and the island, with year-round service centered on Vineyard Haven and seasonal Oak Bluffs service. Passenger-only operators serve additional mainland ports seasonally, and flights use Martha’s Vineyard Airport. Verify the operator, arrival town, parking, and onward transportation together.
Not for every trip. Edgartown, Oak Bluffs, and Vineyard Haven can support car-free stays using walking, VTA buses, bicycles, taxis, and rideshare availability. A car is useful for dispersed up-island plans, but vehicle ferry space requires a reservation and summer traffic and parking can reduce the benefit.
Traditional Steamship Authority ferries generally do not require passenger reservations, while vehicle travel on the Woods Hole–Martha’s Vineyard route is reservation-only. Policies and schedules can change, so check the official reservation page before travel.
July and August offer the fullest seasonal calendar and the greatest crowds and prices. June and September can balance activity with lighter demand, but not every business keeps the same schedule. From late fall through spring, expect a quieter island and more limited dining, lodging, and transportation.
The island has an extensive shared-use path network, but it contains major gaps and does not create a fully protected loop through every town. Choose a route appropriate to ability, use lights and helmets, expect road riding in places, and check the current map rather than relying on a simplified mileage claim.
Martha’s Vineyard is larger and divided among six towns with more varied landscapes and town personalities. Nantucket is more compact around one dominant historic town. Both are seasonal islands where ferry logistics, lodging costs, and advance planning matter.
Explore More