luxury seaside house for rent Aquinnah, United States

Chip Chop is the legendary 20-acre beach compound set on Vineyard Sound. The property has lived large in Martha's Vineyard lore since the 1940s when it was built for celebrated Broadway star Katharine Cornell. For many decades it has hosted a broad spectrum of well-known figures from the worlds of literature, theater, cinema, and politics. A mile of private shoreline surrounds the property, including 2000 feet of sandy beach on the exquisite swimming waters of Vineyard Sound, and a large swath of sandy beach on Lake Tashmoo. Features include a two bedroom main house, outside of which sit the Pond Cottage and the Ocean Cottage, two separate, detached bedroom suites. There are also two elegant guest houses, "Naushon" and "Cuttyhunk", which offer astonishing water views on Martha's Vineyard. The swimming pool overlooking Vineyard Sound with views of the mainland beyond is simply stunning. A Har-Tru tennis court is discretely nestled in a private corner of the property. Additional sleeping space is available in the Rose Cottage, featuring two bedrooms and one bath, full kitchen, and a gorgeous laundry facility. Supremely stylish and yet consummately casual, this famed Martha's Vineyard compound is the perfect setting for your dream Martha's Vineyard getaway.

Pond Front Luxury Retreat Discover this stunning 7-bedroom, 9-bathroom estate set on 9 private acres along Martha’s Vineyard’s picturesque South Shore. This newly constructed property masterfully blends elegance, comfort, and breathtaking water views. Property Highlights: Heated saltwater pool & spa (16' x 42') for ultimate relaxation Expansive screened porch with a wood-burning fireplace & soaring 11-ft ceilings Gourmet chef’s kitchen featuring Thermador appliances, quartz countertops & a spacious island Butler's pantry complete with additional refrigerator and dishwasher Outdoor kitchen perfect for al fresco dining Outdoor kitchen perfect for al fresco dining Multiple suites & private decks, offering stunning views & tranquil privacy Primary suite on the main floor with a spa-like ensuite & private outdoor shower Five bedroom suites with king beds and private baths, 2 additional guest bedrooms share a hall bath Media room, reading nook & lounge areas designed for both entertainment & retreat Two-car garage with an electric vehicle charger Step into the grand living room, where floor-to-ceiling glass doors lead to a mahogany deck, heated pool, and a private boardwalk to the water. Whether you're kayaking, paddle boarding, or simply soaking in the scenery, this home offers unparalleled waterfront living. Located just minutes from Morning Glory Farm, Edgartown Village, Vineyard Golf Club, and the airport, this secluded haven provides effortless access to the island’s finest offerings. Your dream Vineyard escape awaits! *2 week minimum preferred

Experience the pinnacle of Vineyard living at this extraordinarily updated 9-acre estate, nestled within the exclusive Herring Creek Farm Association. Set along the tranquil shores of Edgartown Great Pond, this 10,000+ square foot residence offers unmatched privacy, refined elegance, and direct access to pristine beaches. The main level showcases timeless design with a grand foyer, sweeping staircase, sunlit formal dining room, gourmet chef’s kitchen, and multiple living areas designed for both relaxation and entertaining. A separate guest wing ensures comfort and privacy for visitors. French doors open to a resort-style outdoor oasis with a heated pool, expansive bluestone patio, and a covered porch with fireplace for elegant al fresco dining. Upstairs, five spacious bedrooms include an expansive primary suite featuring a private balcony with water views, a large walk-in closet, private office, and spa-like bath. Spend your days lounging poolside, enjoying sunset views over the Pond, or following a short private path to your own sandy beach. The Association’s exclusive Atlantic beach is a short golf cart ride away. Framed by beautifully landscaped grounds and open farm fields, this exceptional property offers total seclusion just minutes from downtown Edgartown.

Stunning post-and-beam waterfront retreat with sweeping views of Sengekontacket Pond, a private sandy beach, four bedrooms plus two bonus sleeping areas, three full baths, two half baths, and an outdoor shower. Guests enjoy direct pond access along with kayaks and paddleboards included in the rental, perfect for easy Vineyard summer days on the water. Designed for effortless one-floor living, the home features soaring exposed beam ceilings and expansive walls of windows that seamlessly connect indoor and outdoor spaces. The great room is the heart of the home, offering panoramic water views and comfortable gathering space. A chef’s kitchen with premium appliances and generous counter space flows beautifully into the dining and living areas, making entertaining relaxed and enjoyable. The primary suite is privately situated in its own wing, creating a peaceful retreat. Three additional bedrooms are anchored by a shared living area and screened porch, offering ideal separation for families or guests. Flexible sleeping arrangements continue with a pull-out sofa in the office, as well as a separate cottage featuring a TV lounge, pull-out sofa, and half bath perfect for teens, extended family, or overflow guests. Tucked within a quiet waterfront enclave yet conveniently close to all down-island towns, this exceptional vacation rental offers the perfect balance of privacy, comfort, and easy access to everything Martha’s Vineyard has to offer.

Tucked away at the end of a private cul-de-sac in Katama, this expansive property offers the perfect blend of privacy, comfort, and style. The sun-filled first floor boasts an open-concept layout featuring a chef’s kitchen, dining area, and a spacious main living room, ideal for entertaining or relaxing with family and friends. Two additional sitting rooms on the main level provide ample space for guests to unwind. The luxurious primary suite with an en suite bath is also located on the first floor, along with a convenient powder room and one of two laundry areas. The second floor features three beautifully appointed guest suites and a second laundry room for added convenience. The finished lower level is a standout feature, offering an additional king bedroom, full bath, large living area, game room, sauna, home gym, and additional sleeping accommodations, perfect for larger groups or families. Step outside to your own private oasis, a meticulously landscaped, fenced-in yard with a heated pool and hot tub, perfect for enjoying warm summer days and starry Vineyard nights. Located just minutes from South Beach and downtown Edgartown, this Katama retreat offers the ideal Vineyard vacation experience. *Available for 2 consecutive weeks only summer 2027

Exclusive oceanfront on Penzance Point - A Classic Cape Cod Summer Awaits. Nestled in the private enclave of Penzance Point, this nostalgic Cape offers a rare blend of seclusion, charm, and sweeping water views. This spacious oceanfront haven hosts 5 bedrooms and 3.5 baths, with stunning vistas from every room and an expansive deck that wraps the home, drawing you into the natural beauty of Buzzards Bay and Woods Hole Harbor. Watch the steady rhythm of boat traffic by day and toast unforgettable sunsets by night. The sun-drenched living room opens effortlessly onto the deck, creating the perfect flow for summer entertaining and relaxed coastal living. A well-equipped kitchen and pantry make dining easy, whether you're whipping up a simple lunch or a seafood feast. Let the sound of rolling waves lull you to sleep, and wake to sea breezes and salt air. Just minutes away, discover the charm of Woods Hole Village and downtown Falmouth with its laid-back eateries, boutique shopping, and maritime allure. Your Cape Cod summer starts here. Rental Terms: Summer Weekly: $7,000 Per Week

A Cape Cod Quintessential summer retreat with spectacular views of the Ocean and saltmarsh. A wonderful home to create those Cape Cod Memories. This home is located in the Sippewissett area in desirable West Falmouth. The private association beach is steps away where you can swim, sun, kayak and paddle board. With west facing views you will be mesmerized by the amazing sunsets of West Falmouth. This home has a terrific floor plan for large families with numerous gathering areas, and private sitting areas There are views from nearly every room of the home. With close proximity to downtown Falmouth and Woods Hole, you will be able to enjoy the shopping, restaurants, and access the ferry boat to Martha’s Vineyard. No Availability left for 2021. Rental Terms: Summer Weekly: $3,900 Per Week