Martha’s Vineyard is often divided into two distinct regions: “down-island” (the more populated eastern towns of Vineyard Haven, Oak Bluffs, and Edgartown) and “up-island” (the quieter western towns of West Tisbury, Chilmark, and Aquinnah). While down-island offers vibrant town life and easy access to amenities, up-island provides something increasingly precious: seclusion, natural beauty, and a slower pace that feels worlds away from everyday life.
Two exceptional properties exemplify up-island luxury: Lambert’s Cove Inn & Resort in West Tisbury and The Inns at Menemsha (including Menemsha Inn & Cottages and Beach Plum Inn) in Chilmark.
Lambert’s Cove Inn & Resort: Eight Acres of Tranquility
Imagine a property that spans eight acres of pristine island landscape—sprawling lawns, mature trees, gardens, and enough space that you can truly disconnect from the outside world. That’s Lambert’s Cove Inn & Resort.
A Boutique Resort in the Country
Lambert’s Cove manages to be both a boutique inn and a full-service resort—a rare combination. The property offers the personalized service and intimate atmosphere of a small inn while providing resort-level amenities that make extended stays comfortable and convenient.
The Eight-Acre Advantage
Space is luxury. In an era when properties are often built to maximize room count, Lambert’s Cove takes the opposite approach. The eight-acre setting means:
- Privacy – Accommodations are spread across the property, not stacked on top of each other
- Natural beauty – Mature landscaping, gardens, and preserved natural areas
- Outdoor activities – Room to walk, explore, and simply be outside
- Peaceful atmosphere – No sense of crowding or noise from neighboring guests
Private Beach Access
Lambert’s Cove Beach is consistently rated one of Martha’s Vineyard’s most beautiful beaches. Having private access means you can enjoy this stunning location without the crowds that flock to public beaches in summer.
The beach features calm waters, soft sand, and a more secluded feel than down-island beaches. It’s the kind of place where you can spend an entire day without seeing more than a handful of other people.
Pool and Grounds
The property’s pool provides an alternative to beach swimming, surrounded by those sprawling lawns that invite guests to spread out a blanket, read a book, or simply soak in the peaceful atmosphere.
The grounds themselves are an attraction. Walking the property, you’ll discover quiet corners, garden areas, and views that remind you why Martha’s Vineyard has been a beloved retreat for generations.
Farm-to-Table Dining
Up-island is the agricultural heart of Martha’s Vineyard, home to many of the island’s farms. Lambert’s Cove takes full advantage of this location with farm-to-table dining that showcases local ingredients at their peak.
Having excellent on-site dining is particularly valuable in an up-island location, where restaurant options are more limited than down-island. You can enjoy exceptional meals without leaving the property—perfect for romantic dinners or when you simply want to relax after a day of exploration.
The Inns at Menemsha: Seaside Charm and Ocean-Front Views
The fishing village of Menemsha is one of Martha’s Vineyard’s most iconic locations—a working harbor that has retained its authentic character despite the island’s evolution into a high-end destination. The Inns at Menemsha include two distinct properties that let you experience this special place: the historic Menemsha Inn & Cottages and the seaside Beach Plum Inn.
Menemsha: A Working Harbor with Soul
Before diving into the properties, it’s worth understanding what makes Menemsha special. This is a real fishing village—not a tourist recreation. Commercial fishing boats still work out of the harbor. Lobster traps line the docks. The fish markets sell catches that were swimming hours earlier.
But Menemsha is also famous for its spectacular sunsets. The western-facing harbor provides unobstructed views of the sun sinking into the ocean—a nightly show that draws visitors from across the island.
Historic Charm at Menemsha Inn & Cottages
The Menemsha Inn & Cottages offers historic accommodations with up-island charm. The property provides a range of options, from inn rooms to private cottages—ideal for different travel styles and group sizes.
The cottages are particularly appealing for families or groups who want more space and privacy. Having your own cottage in Menemsha means you can settle in, establish routines, and truly live like a local—at least temporarily.
Seaside Luxury at Beach Plum Inn
The Beach Plum Inn takes the Menemsha experience upscale, offering ocean-front views and refined accommodations. This is where you stay when you want the seclusion and authenticity of up-island combined with luxury amenities and service.
The ocean-front views are the star attraction. Waking up to water views, watching the light change throughout the day, and witnessing those famous Menemsha sunsets from your room—these are the moments that define a memorable vacation.
Private Beach Access
Like Lambert’s Cove, The Inns at Menemsha offer private beach access—a significant advantage in an area where beach parking can be limited. You can come and go as you please, avoid crowds, and enjoy the coastline at your own pace.
Why Choose Up-Island?
Authentic Island Character
Up-island feels more like “real” Martha’s Vineyard—the island as it was before it became a celebrity destination. The landscape is more rural, the pace is slower, and the connection to the island’s agricultural and fishing heritage is stronger.
Natural Beauty
The up-island landscape is stunning: rolling hills, stone walls, farms, forests, and dramatic coastline. This is where you’ll find:
- Aquinnah Cliffs – The island’s most dramatic natural feature
- Lucy Vincent Beach – A beautiful, less-crowded beach (residents only during summer, but accessible to all in shoulder seasons)
- Menemsha Hills Reservation – Hiking trails with spectacular views
- Working farms – Many open to visitors for farm stands and tours
Seclusion and Privacy
Up-island properties are inherently more private than down-island accommodations. Lower density, larger properties, and fewer tourists create an atmosphere of seclusion that’s increasingly rare.
Sunset Views
The western orientation of up-island means superior sunset viewing. Menemsha in particular is famous for its sunsets—many visitors make the drive from down-island just to watch the sun set over the harbor.
The Up-Island Lifestyle
Slower Pace
Up-island operates on island time—and then slows down even more. There’s less traffic, fewer crowds, and a general sense that rushing is unnecessary. This pace is either exactly what you’re looking for or a significant adjustment, depending on your travel style.
Limited Commercial Development
Up-island has far fewer shops, restaurants, and commercial establishments than down-island. This is by design—the area has resisted development to preserve its rural character. What this means for visitors:
- Plan ahead – Don’t expect to find convenience stores or late-night dining options
- Embrace the quiet – Entertainment is nature, not nightlife
- Appreciate authenticity – What you lose in convenience, you gain in genuine island character
Farm Stands and Local Food
Up-island is where you’ll find the island’s best farm stands—often just honor-system boxes where you leave cash for fresh vegetables, eggs, or flowers. It’s a reminder of a simpler time and a testament to the community’s trust and values.
Activities and Attractions
Menemsha Sunset Ritual
Watching the sunset from Menemsha is a must-do island experience. The ritual typically involves:
- Picking up fresh seafood from Larsen’s Fish Market or The Bite
- Finding a spot on the beach or harbor
- Enjoying your meal as the sun descends
- Watching the sky transform through shades of orange, pink, and purple
It’s simple, perfect, and quintessentially Martha’s Vineyard.
Aquinnah Cliffs
The dramatic clay cliffs at Aquinnah are the island’s most photographed natural feature. The cliffs rise 150 feet above the beach, displaying layers of clay in various colors. It’s a geological wonder and a cultural landmark—this is Wampanoag land, and the area has deep indigenous history.
Hiking and Nature
Up-island offers the island’s best hiking, with trails through forests, along coastline, and up hills that provide panoramic views. The Menemsha Hills Reservation is particularly spectacular.
Farm Visits
Many up-island farms welcome visitors. You can tour working farms, buy fresh produce, and learn about the island’s agricultural traditions. Some farms offer special experiences like farm dinners or workshops.
Choosing Your Up-Island Property
Choose Lambert’s Cove Inn & Resort if you:
- Want a central up-island location (West Tisbury)
- Value extensive grounds and space
- Prefer a resort feel with boutique service
- Want excellent on-site dining
- Appreciate a pool in addition to beach access
- Like having room to explore on the property itself
Choose The Inns at Menemsha if you:
- Want to be in the heart of Menemsha village
- Prioritize ocean-front views and sunset watching
- Love the atmosphere of a working fishing harbor
- Want easy access to Menemsha’s fish markets and beaches
- Prefer a more intimate, village-based experience
- Are drawn to historic properties with authentic character
Practical Considerations
Transportation
Up-island is less accessible by public transportation, so having a car is highly recommended. The drive from down-island takes 20-30 minutes, which feels longer on island time but is actually quite manageable.
Dining Options
Restaurant options are limited up-island, so properties with on-site dining (like Lambert’s Cove) are particularly valuable. That said, the few restaurants that do exist up-island are often exceptional—The Beach Plum Inn’s restaurant, for example, is highly regarded.
Seasonal Considerations
Up-island is beautiful year-round, but the experience varies significantly by season:
- Summer – Full services, warm beach weather, but also peak crowds (though still quieter than down-island)
- Fall – Spectacular foliage, harvest season at farms, fewer crowds
- Winter – Very quiet, many businesses closed, but dramatic coastal scenery
- Spring – Blooming landscapes, moderate weather, increasing activity
The Up-Island Appeal
Choosing to stay up-island is choosing a different kind of vacation. It’s not about shopping, nightlife, or constant activity. It’s about:
- Waking to birdsong instead of traffic
- Measuring time by tides and sunsets rather than schedules
- Experiencing natural beauty without crowds
- Connecting with the island’s agricultural and maritime heritage
- Finding space—physical and mental—to truly relax
Lambert’s Cove Inn & Resort and The Inns at Menemsha provide the perfect bases for this experience. They offer comfort and amenities while honoring the up-island ethos of simplicity, authenticity, and connection to place.
If you’re seeking the Martha’s Vineyard that exists beyond the boutiques and busy harbors—the island of farms and fishing villages, dramatic cliffs and quiet beaches, spectacular sunsets and star-filled skies—up-island is calling. And these properties are ready to welcome you.