luxury real estate 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.

Experience breathtaking views of Sengekontacket Pond, State Beach, and all the way to Chappaquiddick from this stunning newly built property. Overlooking the third, fourth, and fifth holes of the renowned Farm Neck Golf Club, this home offers the perfect balance of natural beauty and luxury. The expansive Great Room features panoramic vistas, while the property includes 5 spacious bedrooms, 6 full baths, and a large lower-level rec room complete with additional sleeping space, kitchenette, and ping pong table. There are two sets of washers and dryers included, one on the main level and one in the lower level. Step outside onto the generous deck facing the water, or relax in the serene bluestone patio courtyard. After a day at the beach, kayaking, or a round of tennis at nearby Farm Neck, rinse off in one of the two convenient outdoor showers. The property is located within the Waterview Farms community, which boasts miles of scenic walking trails and association beach access on Sengekontacket Pond. For those looking to explore more, it's just a short paddle to the lively State Beach. Perfect for a truly unforgettable vacation!

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

Woods Hole furnished rental. This modern home was built in 2024 with attention to detail & high-end finishes. Enjoy the proximity to Woods Hole Village offering world class restaurants, artisan shopping, boating, fishing, and tennis. Spend time exploring Martha's Vineyard, the ferry is a short distance from this home. Also close by is the Woods Hole entrance to the Shining Sea Bike Path a 10.7-mile trail through Falmouth with stunning views of beaches, salt marshes & harbors for walkers, cyclers, & runners to enjoy. Stoney Beach, Nobska Beach & Lighthouse, the Knob, Marine Biological Laboratories, Woods Hole Oceanographic Institute, the Woods Hole Science Aquarium, and the Children's School of Science are also convenient to this fully furnished, modern home. Large finished basement with a ping pong table and full size washer and dryer. Enjoy the high ceilings, natural light and open spaces this newly remodeled home offers. All of the furnishings are new including the kitchen cookware and dinnerware. This is a wonderful, furnished Woods Hole rental for your in season monthly stay or your off season monthly stay to experience the quaint & charming Woods Hole Village life-style. Rental Terms: Summer Weekly: $7,000 Per Week Summer Monthly: $24,000 Per Month Other / Short Term - per month off season: $4,000

Set on just under an acre of beautiful, private, manicured grounds, this furnished five-bedroom, four-bath contemporary home offers an exceptional rental opportunity just minutes from the village of Woods Hole. Featuring soaring ceilings throughout, the home boasts a generous, open, light-filled floor plan designed for comfortable coastal living. The chef's kitchen is outfitted with a Viking range, Sub-Zero refrigerator, and ample space for entertaining. A large, elegant private patio with table and chairs is just off the kitchen for al fresco dinning. With its spacious interiors, modern amenities, and serene private setting, this exceptional property is an ideal Woods Hole retreat. The winter/off season rental rate is $5,000 per month plus utilities. The Summer (July & August) weekly rate is $6,500 per week including utilities. Sept. & June: $4,000 per week utilities included. Please reach out with your rental needs. Rental Terms: Other / Short Term - Monthly: $5,000

There are places that remind you of a different time. Where mornings begin with coffee on the porch. Children spend the day barefoot on the lawn, and evenings end with the sun disappearing into the water while everyone lingers just a little longer. Set on four private waterfront acres in Woods Hole, 122 Gansett Road captures the spirit of old Cape Cod--unhurried, welcoming, and deeply connected to the sea. Thoughtfully modernized, the home preserves its timeless character while offering every comfort expected today. A new chef's kitchen, updated baths, six bedrooms, and generous gathering spaces make it ideal for family vacations that become lifelong traditions. Outside, the days unfold naturally. Swim in the heated pool, relax in the spa, challenge friends to a game of pickleball, wander down to the private association beach, or simply settle into an Adirondack chair and watch one of the Cape's unforgettable sunsets. Just minutes from Woods Hole Village, you'll find charming restaurants, ferry service to Martha's Vineyard, scenic walking trails, and quiet beaches that have drawn generations here. Availability last week in July, August, September and October. $15,500 per week. Rental Terms: Summer Weekly: $15,500 Per Week

Experience coastal sophistication and serene living at 1 Shoreline Drive, located in one of Falmouth’s most desirable seaside neighborhoods. This beautifully furnished, contemporary home offers the perfect blend of elegance, functionality, and comfort — all just minutes from Portland’s vibrant Old Port and surrounded by the natural beauty of Maine’s coastline. Wake up to ocean breezes and spend your evenings on the deck enjoying sunset views. Property Features: 4 Bedrooms | 3.5 Bathrooms | Unfurnished Spacious, light-filled living designed for modern coastal living across three levels First Floor - Main House: Open-concept kitchen featuring quartz countertops, high-end stainless steel appliances, custom cabinetry, and a large island ideal for gathering Inviting dining area and living room with oversized windows that frame water views Primary suite, en-suite bathroom with a walk-in shower, and ample closet space Convenient half bath and laundry area Enclosed three-season pation with an additional screened in porch Access to a private deck overlooking tranquil, landscaped grounds — perfect for morning coffee or evening relaxation Second Floor – Main House: Two additional bedrooms with abundant natural light Full bathroom with modern finishes Additional family room or media space for comfortable lounging Apartment Above 2-Car Garage: Private suite featuring a queen-sized bed Full bathroom Counter space and mini fridge — ideal for guests, in-laws, or a private home office setup Lease Details: Available for long-term lease at $6,000/month Tenant responsible for utilities, landscaping and snow removal No smoking Additional Highlights: The home was thoughtfully designed with both energy efficiency and long-term comfort in mind. Built to maximize sustainability, it features a convection range and a hybrid furnace for optimal performance and reduced energy use. It was also constructed with lifelong living and accessibility in mind — the front entry can easily accommodate a ramp if needed, and once inside, the first-floor layout, primary suite, wider doorways, and no-step shower allow for comfortable, safe, and accessible living for years to come. Contact Legacy Properties Sotheby’s International Realty for more information or to schedule a private showing.

Legacy Properties Sotheby's International Realty is proud to present to you 7 Old MIll Road in Falmouth. Offered on a long term rental basis. This updated three bedroom three bathroom home has garage parking for at least one vehicle and possibly two if parking tandem. This home is not furnished. Located behind Skillins Greenhouse. Minutes to 295 or the Falmouth Connector to get onto I95. Or moments down route 1 to get to downtown Portland. Utilities not included.

Discover unparalleled refined living in Unit 505 at The Wyeth, a top-floor, corner residence offering two bedrooms, two baths, and sun-filled interiors framed by expansive east-facing windows. This fully furnished condo blends sophisticated design with comfort, creating a turnkey retreat in the heart of Falmouth. Step onto your private balcony and savor peaceful vistas of the pond and surrounding natural landscape. Inside, the chef’s kitchen is appointed with premium appliances and crisp finishes, flowing seamlessly into open-concept living and dining areas perfect for entertaining or relaxing around the cozy fireplace. The space is enhanced by remote-control blinds for effortless light and privacy and features new, neutral, and sleek furnishings throughout. The primary suite provides a private sanctuary with a luxurious en-suite bath, while the second bedroom offers flexibility for guests, a home office, or a personal retreat. Additional conveniences include an in-unit washer and dryer for easy living. High-end finishes, thoughtful details, and abundant natural light define every corner of this exceptional condo. The Wyeth elevates the living experience with resort-style amenities: a fully equipped gym, expansive rooftop terrace with firepits, a sophisticated community club room, secure mail room, and private storage space, covered and heated underground parking and elevator access ensure ease and convenience year-round. Ideally situated in the heart of Falmouth, this residence places you just steps from boutique shopping, cafes, fine dining, beaches, coastal waterfront, and scenic walking trails, with easy access to nearby nature preserves. Enjoy the added convenience of multiple gyms, supermarkets, and restaurants, along with effortless connectivity via the Turnpike and Route 295. Just minutes from Portland, the Jetport, and major highways, this prime location offers unmatched access for work, play, and weekend escapes. A rare opportunity to lease and enjoy a turnkey, top-floor luxury condo in one of Southern Maine’s most desirable communities. Available for long-term lease now. $4,750 / month plus electricity and wifi.

Legacy Properties Sotheby's International Realty is delighted to introduce the elegant residence at 239 Foreside Road in Falmouth, Maine. Nestled in the prestigious Falmouth Foreside area, this home features four inviting bedrooms, complemented by two full and two half bathrooms, distributed as follows: Main Floor: Master bedroom with a king-sized bed, accompanied by an infrared sauna and a full bathroom with a luxurious soaking tub. Upper Floor: Offers a double bed, two twin beds, and a queen bed across three bedrooms, alongside a fitness area equipped with a rowing machine and free weights. The architecture of the home adds a unique charm with a second-floor hallway featuring a gently sloping ceiling, while an alternative staircase provides easy access to all upstairs bedrooms. Outdoor living is equally impressive with a heated pool set within a vast, inviting deck area. The lower level adds a playful touch with a ping pong table and additional half bathroom. Located just minutes from the tranquil Mackworth Island, with its laid-back waterfront trails and a mix of sandy and rocky beaches, the home also offers proximity to Town Landing, where you can stroll on more beaches or visit the local market for a quick grocery run or a delightful sandwich lunch. The property’s prime location allows for easy access to Route 1, leading to downtown Portland or further explorations along Maine’s scenic coast. To enhance your stay, inquire about our exclusive private chef services. Contact Legacy Properties Sotheby’s International Realty for more details on this luxurious Falmouth Foreside home.

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