A view of the Hilltop Haven main house from the backyard.
Perched on a gentle hill just outside the heart of Vineyard Haven, this beautifully restored historic home offers the perfect blend of classic Martha’s Vineyard charm and modern comfort. With nearly 2,800 square feet of thoughtfully designed living space, four bedrooms, three bathrooms, multiple gathering areas, and inviting outdoor spaces, it is a place where families and friends can truly settle in, reconnect, and enjoy island life.
Step inside and feel the pace of life slow down. High ceilings, oversized windows, and abundant natural light create a sense of openness throughout the home. Gentle Vineyard breezes drift through the living spaces, while comfortable furnishings invite long conversations, afternoon reading, or movie nights with the people you love. The spacious dining room is designed for gathering, whether over leisurely breakfasts, fresh seafood dinners, or celebrations that linger late into the evening.
One of the home's most beloved features is the sunny window-seat book nook, a cozy retreat for reading, daydreaming, or simply enjoying a quiet moment. Nearby, the bright three-season room offers additional living space for relaxing, working remotely, playing games, or accommodating extra guests. Many visitors choose to sleep here, waking to the morning sunlight streaming through the windows.
The kitchen is fully equipped for serious cooking and casual entertaining alike, featuring premium appliances, quality cookware, and everything needed to prepare memorable meals. A spacious mudroom and laundry area provide a full-size washer and dryer, utility storage, and practical convenience for beach days and family vacations.
The bedroom layout offers flexibility for couples, families, and multi-generational groups.
On the first floor, a comfortable double bedroom sits adjacent to the window-seat area and includes a private ensuite shower room. This bathroom is architect-designed and intentionally compact, reminiscent of a yacht cabin, with the shower and toilet sharing the same space.
Upstairs, the primary king bedroom features a lovely sitting area and a glimpse of the water. A queen bedroom includes its own ensuite bathroom, while a charming bunk room offers a full bed below and a twin bed above, making it ideal for children or additional guests. A full family bathroom serves the king and bunk rooms.
Additional sleeping options include a queen sofa bed in the three-season room, a full sofa bed in the living room, and the spacious window-seat nook that many guests find surprisingly cozy for sleeping.
Throughout the home, modern comforts blend seamlessly with historic character. Individual climate controls provide air conditioning and heat, while high-speed internet, streaming television, a fully equipped kitchen, hair dryers, ironing facilities, and multiple heating options—including a pellet stove for cooler seasons—ensure a comfortable stay year-round.
Outside, the property truly shines. A large deck provides ample seating for outdoor dining and gathering. Fire up the Weber grill for summer cookouts, relax in Adirondack chairs around the fire pit, rinse off in the outdoor shower after a day at the beach, or enjoy the fenced area for dogs. The side yard offers additional space to unwind beneath Vineyard skies.
The location is one of the home's greatest advantages. From this peaceful hilltop setting, guests can easily walk to many of Vineyard Haven's favorite destinations. The Martha's Vineyard Museum is just a two-minute stroll away. The Lagoon, with kayak and boat rentals, is a short walk downhill. Downtown Vineyard Haven's restaurants, shops, galleries, and historic streets are easily accessible, while Owen Park Beach and Eastville Beach are both nearby. Children can enjoy nearby playgrounds and playing fields, while adults can spend the day exploring the harbor, paddling on the Lagoon, shopping in town, or simply enjoying the island's relaxed pace.
For larger groups, please note that while the home comfortably accommodates many guests and has welcomed numerous multi-generational families who return year after year, we encourage you to review the sleeping arrangements carefully to ensure the layout is the perfect fit for your group.
Also located on the property is a separate, beautifully renovated one-bedroom cottage, available as an additional vacation rental. The cottage has its own private yard, outdoor shower, grill, fire pit, washer and dryer, well-equipped kitchen, and comfortable sleeping arrangements, making it an ideal option for extended family, grandparents, or friends traveling together while still enjoying their own private space.
Well-behaved dogs are welcomed and loved. Please contact us regarding our pet policy.
CONTACT US for availability, rates, and reservations. Guests who book directly receive personalized service and preferred pricing.
If you prefer to book through Airbnb, you may also view rates, availability, and reviews here.