If you’ve ever tried to book a room in Menemsha during the height of July, you know the feeling. It's a mix of desperation and awe. You’re looking for that specific, salty-air magic that only the western tip of Martha’s Vineyard provides. Most people start their search by looking for the Plum Inn Martha's Vineyard, thinking they’ve found a hidden gem. Well, they have, but there’s a catch that catches almost everyone off guard: it’s actually the Menemsha Inn and Cottages that holds the keys to what many refer to as the "Plum Bush" or "Plum" area properties.
It's confusing. Honestly, the geography of Chilmark lodging is a bit of a maze if you aren't looking at a local survey map.
The reality of staying out here is different than staying in Edgartown or Oak Bluffs. You aren't here for the nightlife. You're here because you want to see the sun melt into the Vineyard Sound while eating a lobster roll on a cold plastic bucket. It's raw. It's quiet. And if you’re looking for the Plum Inn Martha's Vineyard, you’re likely looking for the specific quietude of the Menemsha Inn’s "Plum Bush" suites.
The Geography of the Plum Inn Martha's Vineyard Area
Let's get the logistics out of the way first. Menemsha is a tiny fishing village within the town of Chilmark. It is, arguably, the most photographed spot on the island. When people talk about the Plum Inn Martha's Vineyard, they are usually referring to the accommodations associated with the Menemsha Inn, specifically the Plum Bush building.
This isn't a massive resort. Not even close.
The Plum Bush area is tucked away, surrounded by actual plum bushes and beach grass. You’ve got these cedar-shingled buildings that look like they’ve been there since the whaling days, even if they’ve been meticulously updated inside. If you want a marble lobby and a concierge in a suit, go back to the mainland. Here, luxury is defined by a private screened-in porch and the fact that you can walk to the beach without fighting for a parking spot—which, in Menemsha, is a miracle.
Most rooms in this cluster offer king-sized beds, private decks, and that distinct "up-island" vibe. It’s understated. You’re paying for the silence. You're paying for the fact that the only thing you hear at night is the distant groan of a fishing boat or the wind through the scrub oaks.
Why Staying Up-Island is a Different Beast
Most Vineyard tourists stay "down-island." They want the shops. They want the crowds. Staying at a place like the Plum Inn Martha's Vineyard (or the Menemsha Inn) means you are making a conscious choice to leave the noise behind.
📖 Related: Food in Kerala India: What Most People Get Wrong About God's Own Kitchen
Chilmark has some of the strictest zoning and preservation laws in the country. This means there are no neon signs. There are no fast-food joints. There aren't even many streetlights.
If you stay at the Plum Bush suites, you get access to things most visitors never see. For instance, guests usually get passes to Lucy Vincent Beach or Squibnocket. These are "private" beaches restricted to town residents and certain lodgers. If you’ve seen photos of those dramatic clay cliffs and crashing Atlantic waves that look like a scene from a movie, that’s Lucy Vincent. Without a pass, you aren't getting in. Period.
The Sunset Ritual
You can't talk about Menemsha without talking about the sunset. It is a legitimate event. People drive from all over the island, clutching bottles of wine (Chilmark was a dry town for a long time, though you can buy beer and wine at certain spots now) and boxes from Larsen’s Fish Market or The Net Result.
Staying at the Plum Inn Martha's Vineyard area means you don't have to worry about the traffic nightmare that happens twenty minutes before dusk. You just walk down the hill. You find a spot on the jetty. You watch the colors change. Then, when everyone else is stuck in a line of cars trying to get back to Vineyard Haven, you just walk back to your room. That’s the real flex.
What Most People Miss About the Accommodations
There’s a common misconception that "inn" means "old and dusty."
While the aesthetic is classic New England, the interiors of the Plum Bush suites are surprisingly modern. We’re talking about high-end linens, clean lines, and often, outdoor showers. If you’ve never taken a shower outdoors while looking at the stars, you haven't lived. It sounds weird to mainlanders, but on the Vineyard, an outdoor shower is a status symbol and a spiritual experience wrapped into one.
The Menemsha Inn, which manages the Plum properties, also offers things like:
👉 See also: Taking the Ferry to Williamsburg Brooklyn: What Most People Get Wrong
- Tennis courts (har-tru)
- A fitness center (for those who don't find hiking the hills enough)
- Freshly baked items for breakfast
- Bikes for exploring the winding roads of Chilmark
But here is the thing: it’s expensive. You’re paying for the location. You’re paying for the exclusivity of Menemsha. You’re also paying for the peace of mind that comes with knowing your "neighbors" are probably just some deer and the occasional celebrity trying to hide out in a sun hat.
Practical Realities of an Up-Island Stay
Don't arrive here expecting a 24-hour CVS.
If you stay at the Plum Inn Martha's Vineyard, you need to plan. The Chilmark General Store is your lifeline. They have the best pizza, great coffee, and the "porch" which is basically the town's social hub. But they close. Everything up here closes earlier than you think.
You also need a car. Or at least a very good pair of legs for biking. While the inn is walkable to the harbor, if you want to see the rest of the island, you’re looking at a 20-to-30-minute drive to get to "civilization."
A Quick Word on Booking
The "Plum" rooms are some of the first to go. Because they are slightly removed from the main inn building, they offer a level of privacy that’s hard to find. If you’re planning a honeymoon or a "we need to save our marriage" retreat, this is where you go. But you have to book months—sometimes a year—in advance.
The rates fluctuate wildly. A Tuesday in early June is a different world than a Saturday in August. If you can swing a trip in September, do it. The water is still warm, the crowds are gone, and the light in Menemsha becomes this golden, honey-colored hue that photographers literally lose their minds over.
Actionable Steps for Your Visit
If you're serious about staying at the Plum Inn Martha's Vineyard (or the Menemsha Inn complex), don't just click "book" on a third-party travel site. Those sites rarely have the full picture of what’s available in Menemsha.
✨ Don't miss: Lava Beds National Monument: What Most People Get Wrong About California's Volcanic Underworld
1. Call them directly. The staff at the Menemsha Inn know every corner of the Plum Bush suites. Ask about the specific view from the room. Ask which ones have the best breeze. Sometimes a specific cottage isn't listed online because it’s being held for a returning guest, but if you're nice, they might find a gap for you.
2. Secure your ferry reservation early. This is the mistake that ruins vacations. You can book the nicest room in the Plum Bush area, but if you don't have a car reservation on the Steamship Authority ferry from Woods Hole, you aren't getting your car to the island. Reservations usually open in January. By March, the good times are gone.
3. Pack for "Chilmark Casual." No one wears heels here. No one wears ties. Pack a good fleece (it gets cold at night, even in summer), some sturdy sandals, and a flashlight. There are no streetlights near the Plum area, and navigating the path back from the harbor at 10:00 PM requires some illumination.
4. Plan your meals. Remember that Menemsha is a working fishing port. Buy your fish right off the boat or from the markets. If you want a "fancy" sit-down dinner, you’ll likely head to the Beach Plum Inn restaurant (right nearby) or drive into West Tisbury. The Beach Plum Inn restaurant is one of the few places where you can get a world-class meal with a view of the harbor, but reservations are mandatory and fill up fast.
5. Embrace the disconnect. Cell service in Chilmark is notoriously spotty. The Wi-Fi at the inn is generally fine, but don't count on streaming 4K movies all night. Use the time to actually read a book. There’s a reason famous writers hide out here. The air just makes you want to produce something—or at least think a little deeper.
Staying at the Plum Inn Martha's Vineyard isn't about checking a box on a luxury travel list. It’s about opting out of the "tourist" version of the Vineyard and opting into the "local" version. It’s quiet, it’s expensive, it’s slightly inconvenient, and it is absolutely worth it for the sunset alone.
If you want the best experience, aim for the shoulder season. Late May or early October. You get the same views, half the people, and the staff will actually have time to tell you the best secret spots to find sea glass. Just remember to bring your own wine—the nearest liquor store is a long drive away.