• 4 Bedrooms
  • 3 Bathrooms
  • Sleeps 10
  • No pets
From $8,500 / week

Welcome to your Martha’s Vineyard escape in the desirable Meadow View Farms neighborhood of Oak Bluffs. Surrounded by natural beauty and designed for comfort, this inviting four-bedroom, three-bath home offers over 3,000 square feet of thoughtfully designed living space for families and friends to gather. The main living area is bright and airy, with soaring ceilings, abundant natural light, and an open-concept layout that creates a warm, welcoming atmosphere. The spacious kitchen…

  • 6 Bedrooms
  • 3 Bathrooms
  • Sleeps 14
  • No pets
From $7,500 / week

This lovely yellow cottage is well appointed and close to town and a quick walk to Fuller Beach, ride the bike path out to South Beach or take a stroll into town to walk along the docks. It is beautifully furnished including a fireplace in the living room. Updated kitchen and bathrooms. This Cottage can sleep up to 10 and the guest cottage can accommodate another four.

  • 3 Bedrooms
  • 1.5 Bathrooms
  • Sleeps 8
  • No pets
From $3,000 / week

Experience the effortless beauty of Chappaquiddick from this completely renovated top-to-bottom coastal farmhouse cottage overlooking the sweeping waters at Katama Bay. Thoughtfully reimagined with all-new furnishings, elevated finishes, and a light, airy design aesthetic, this retreat blends timeless Vineyard charm with modern comfort for a truly special island escape. The open-concept living, dining, and kitchen area is the heart of the home, inviting both relaxation and gathering. Expansive sliders open directly to…

  • 4 Bedrooms
  • 4 Bathrooms
  • Sleeps 10
  • Pets allowed
From $6,500 / week

Welcome to 1 Essex Court, a comfortable and versatile Edgartown retreat designed for relaxed summer living and memorable gatherings. Located in the desirable Windsor Drive area, this well-maintained home offers generous indoor and outdoor spaces, making it easy for families and friends to return year after year. The heart of the home is an open living, kitchen, and dining area, where the island kitchen flows seamlessly into the main gathering space—ideal for…

  • 2 Bedrooms
  • 1.5 Bathrooms
  • Sleeps 5
  • No pets
From $2,750 / week

Set against one of Katama’s most picturesque backdrops, 81-A Herring Creek Road is a thoughtfully updated guest house offering style, comfort, and sweeping pastoral views across 50 acres of protected conservation land with open fields, wildflowers, and a working horse barn. With its Western-inspired character and fresh, modern upgrades, this home is both welcoming and unique. Inside, the space feels bright and airy, highlighted by a brand-new kitchen and newly renovated bathrooms…

  • 5 Bedrooms
  • 4.5 Bathrooms
  • Sleeps 10
  • No pets
From $6,000 / week

Located in the heart of Katama, Edgartown, this stunning 3-bedroom, 4.5-bath retreat captures the essence of Martha’s Vineyard living — bright, open, and effortlessly elegant. Bathed in natural light, the home offers a seamless blend of luxury and comfort, featuring spacious living areas, a chef’s kitchen, and expansive decks perfect for morning coffee or sunset cocktails. Just minutes from South Beach and a quick bike ride or drive to Downtown Edgartown’s shops,…

  • 5 Bedrooms
  • 5.5 Bathrooms
  • Sleeps 12
  • No pets
From $10,000 / week

Tucked into the rolling landscape of Chilmark, 50 Putnam Road is a gracious and spacious retreat offering the perfect balance of privacy, comfort, and classic Martha’s Vineyard serenity. With over 3,600 square feet of living space, five bedrooms, and five and a half baths, this home is ideally suited for families or groups seeking a relaxed yet elevated island getaway. The interior is thoughtfully designed for both gathering and retreat. Generous common…

  • 1 Bedroom
  • 1 Bathroom
  • Sleeps 4
  • No pets
From $4,000 / week

Tucked into the heart of Chappaquiddick, this charming cottage offers a cozy queen loft, two twin beds, and an inviting deck with a grill and bistro lighting—all near the Royal and Ancient Golf Course.

  • 3 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 8
  • No pets
From $3,500 / week

Discover a truly special Vineyard escape at 80 Bellevue Avenue, a custom-built 3+ bedroom home offering sweeping water views of Lagoon Pond and a uniquely private setting surrounded by 15 acres of conservation land. This peaceful retreat places you close to Vineyard Haven’s amenities while giving you the tranquility and space of a nature-focused getaway. The main level features a full kitchen and bar area with direct access to an oversized garden…

  • 2 Bedrooms
  • 1 Bathroom
  • Sleeps 4
  • No pets
From $1,400 / week

Wake up overlooking Vineyard Sound at this classic Beach Road cottage, ideally positioned between Oak Bluffs and Vineyard Haven. Designed for a simple, relaxed Vineyard stay, the home offers a private rocky shoreline, a waterfront sitting porch, a separate sun deck and convenient access to nearby beaches and both harbor towns. Inside, the cottage retains its nostalgic island character while offering refreshed flooring, fresh paint and comfortable accommodations for up to four…

  • 4 Bedrooms
  • 2.5 Bathrooms
  • Sleeps 8
  • No pets
From $7,400 / week

Set against a backdrop of protected farmland and open Vineyard skies, Katama Landing is a rare architectural offering that seamlessly blends modern design, luxury amenities, and the natural beauty of Martha’s Vineyard. Thoughtfully designed with clean lines, weathered cedar shingles, dramatic glass walls, and warm walnut flooring, the home creates a sophisticated yet welcoming atmosphere from the moment you arrive. Every detail has been carefully considered, resulting in a residence that feels…