luxury holidays rentals Massachusetts, United States

A truly remarkable residence designed by one of the Island's premier architects and situated midway between the historic village of Edgartown & the golden sands of South Beach. Located just a mile from both this home boasts an outstanding and most desirable location. This elegant five-bedroom home with guest house is set on the prestigious Field Club's manicured 7.5-acre property. This house features everything one would expect in a newly built, high-end home. Added in 2013 the custom pool and spa are in wonderful condition. There are many distinct details that complement the abundant and well-crafted living spaces. There are spacious decks off the bedrooms as well as a covered porch with an outdoor fireplace. The graceful living room offers HD television and a sound system with the bonus of a real log fireplace for romantic evenings. The fully equipped chef’s kitchen includes a top-of-line Wolf Range, granite countertops, two dishwashers, and a separate Butler’s pantry. The comfortable sunroom leads from the kitchen through double French doors to the landscaped garden and the heated 18 by 32 foot swimming pool. Surrounding the pool is an expansive patio that has a six-foot fire pit for alfresco dining. Inside the stylish dining room comfortably seats eight. There's even a relaxing den with a gas fireplace. Finally, the cozy primary bedroom with a gas fireplace and adjoining balcony completes the main house. The Guest House is a separate one-bedroom/one-bath suite above a two-car garage. The garage doubles as a “party room” complete with a ½ bath and Ping-Pong table. $20,000-$35,000/week

Step into this meticulously crafted property where every detail has been thoughtfully curated to create a breathtaking interior. From the moment you enter, you're greeted by elegant design elements that seamlessly blend luxury with functionality. Designer fixtures and bespoke furnishings adorn every corner, elevating the ambiance and setting a tone of refined elegance. This spacious residence boasts six bedrooms, each with its own en-suite bathroom, alongside an additional half bath. It features two primary suites, one on each floor, ensuring comfort and convenience. The first floor encompasses a library, dining room, powder room, great room, kitchen with a walk-in pantry, family room, butler's pantry, and a laundry room. On the second floor, you'll find five bedrooms with attached baths, a home office area, and a second laundry room equipped with two washer/dryer sets. The bedrooms upstairs offer versatile sleeping arrangements, including three with king-sized beds, one with two queens, and a final room featuring a king bed alongside a twin daybed, ideal for families with young children. Additionally, the outdoor amenities include a pool, a covered porch with a fireplace, and an adjacent outdoor eating area with a grill. In every corner of this stunningly designed property, luxury and sophistication converge to create an unparalleled living experience. From the impeccable attention to detail to the seamless integration of indoor and outdoor living, this property is truly exceptional. Located near South Beach and all that downtown Edgartown has to offer.

Exceptional rental opportunity on Menemsha Pond. This stunning compound features a main house with eight ensuite bedrooms, showcasing a remarkable first-floor primary suite with two full bathrooms. Two kitchens, equipped with top-of-the-line appliances, provide a luxurious culinary experience. Additional features include a home theater with massage chairs and expansive indoor and outdoor living spaces against the backdrop of breathtaking water views. Included with the main house is a large waterfront deck with outdoor Italian seating that can comfortably accommodate 20 people. There is an outdoor dining table that can accommodate 24 guests, as well as a large built in Kalamazoo grill and pizza oven, an outdoor wooden bar, an outdoor built in stone fire pit and two large built in Tucci umbrellas. The pool house serves as a haven of relaxation, featuring an indoor heated 10' X 30' pool and a spa surrounded by floor-to-ceiling sliding glass doors that seamlessly blend the interior with the exterior. Additional amenities include a sauna, steam room, wet bar, and two guest bedrooms. The second-floor is a full guest suite, including a large bedroom, washer and dryer, a living room and two spacious balconies.The first-floor guest bedroom enhances the overall luxurious accommodations. Perched atop the compound is a hilltop writer's cottage with one bedroom, offering panoramic views overlooking the pond. Also included on the property is an entertainment building including a large full gym with various cardio and weight machines by Technogym and Peloton. The gym features floor-to-ceiling windows providing scenic views. There is also an indoor basketball court with an NBA professional basketball shooting machine. Below is a 6 car garage with Porsche and Tesla electric car charging stations. Guests can also enjoy outdoor recreational activities with a tennis court that doubles as a pickle ball court with appropriate lines, and a large cedar jungle gym. The property includes a 115' deep-water dock with a boat house featuring numerous waterfront activities including paddle boards, kayaks, and wetsuits for added convenience. Additionally, three purpose-designed boats are available for use during the stay. Guests have the option to rent one, two, or all three: Boat One is a 55-foot Novamarine BS160, custom made in Italy, equipped with 5 outboard Mercury Racing engines and significant customization (captain required). Boat Two is a Mastercraft X26, perfect for water skiing, wake surfing, wakeboarding, etc. The boat features a computer touch panel for creating a customizable surf wave behind the boat. Boat Three is a Zodiac Open 7.0 speed boat, versatile for water skiing and well-suited for navigating open oceans with waves. This 26-foot boat is powered by a Yamaha 200 HorsePower outboard engine, offering both agility and stability on the water. The nearby beaches offer delightful opportunities for sunbathing, swimming, and savoring the picturesque ocean views. Menemsha, a charming fishing village nestled in Chilmark, is celebrated for its delightful harbor, delicious seafood, and enchanting sunsets. From the property itself, guests can enjoy breathtaking views of Menemsha Pond, particularly at sunset, when warm hues paint the sky and cast reflections on the serene waters, creating a tranquil and visually captivating setting. The island plays host to a variety of events and activities, including farmers' markets, art fairs, and community gatherings. The lush green surroundings, invigorating coastal breezes, and overall sense of serenity make it an attractive destination for those in search of an escape. This rental opportunity guarantees an immersive, high-end escape where guests can unwind in a serene atmosphere, surrounded by the beauty of nature and the thoughtful luxury woven into every aspect of the property.

This classic New England home is a true masterpiece of modern living. Nestled on a spacious and meticulously landscaped lot in Katama, this property offers the perfect blend of elegance, comfort, and convenience. The main house features three spacious and beautifully appointed bedrooms, each designed for relaxation and comfort. From the primary suite to the guest bedrooms, every room offers a serene retreat with ample natural light. The main living area is thoughtfully designed with an open-concept layout, creating an ideal space for entertaining. A cozy fireplace and large windows enhance the ambiance, providing both warmth and captivating views of the lush surroundings. The French doors open to a deck overlooking the manicured lawn. A state-of-the-art media room, complete with comfortable seating, a large screen, and high-quality audio-visual equipment. It's the perfect spot for movie nights, game days, or simply relaxing with friends and family along with a wine cellar just steps away. The carriage house features a large one-bedroom and bath upstairs. $7,500 - $24,000/week

This home sits on a unique piece of the Edgartown harbor. With balconies overlooking the harbor, your vista is forever changing. Located on the north side of Edgartown, guests can enjoy views of the harbor as well as the north bluff of Chappaquiddick. While the sun sets to the west, it casts a golden hue over the water, Chappy beyond. If you're an early riser, you will see the vibrant sunrise over Cape Pogue. With four comfortable bedrooms and flowing open common areas, this home is your ultimate vacation destination. Discerningly decorated in a nautical theme, it has old world charm with all of the modern conveniences, including central air conditioning. The property is located one block from all of the entertainment, shopping and dining that Edgartown has to offer. $7,500-$27,500/week

Renovated and decorated by a renowned Island decorator, and featured in Architectural Digest thereafter, this gem sits on a rather unique piece of property overlooking the historic Edgartown harbor. Located on the north side of town, the views are of the immediate harbor as well as the north bluff of Chappaquiddick; during sunrise or sunset the exquisite coloration cast off the harbor is a guaranteed inspiration. With three comfortable bedrooms and flowing open common areas, this home is your ideal vacation spot. Discerningly decorated in nautical theme, it has an old world charm with all the modern conveniences. Located a block from all downtown Edgartown amenities, including Fuller Street Beach. $6,000-$25,000/week

Nestled in the prestigious Field Club, this recently renovated rental property epitomizes luxury and comfort. With five spacious ensuite bedrooms, the home is designed for guests seeking a tranquil yet sophisticated retreat. Two well-appointed primary suites offer privacy and relaxation. Three additional ensuite bedrooms provide ample space and comfort for guests. The cozy den, complete with a gorgeous home bar, is perfect for lounging and entertaining. A bright and airy sunroom, featuring a stunning fireplace, offers a serene space to relax and unwind. Two convenient and beautifully designed laundry rooms cater to the needs of a large household. The stunning outdoor pool and spa complete with pool house, provide the perfect setting for relaxation and enjoyment, surrounded by manicured lawns and elegant landscaping that enhance the property’s charm and appeal. This property combines modern amenities with timeless elegance, offering a perfect blend of comfort and style.

Overlooking Lake Tashmoo in Vineyard Haven, this waterfront rental property offers a luxurious retreat for those seeking relaxation and comfort. Step onto the expansive large deck and be greeted by breathtaking views of the tranquil water, providing the perfect setting for watching the sunset. The property features a charming pool, ideal for refreshing dips on hot summer days or simply lounging by the water's edge, soaking in the peaceful ambiance. The screened porch offers a shaded oasis to enjoy the fresh air and scenic surroundings. Inside guests will find five spacious bedrooms, each offering a retreat-like atmosphere. Two of these bedrooms are ensuite primary bedrooms, conveniently located on both the first and second floors for added privacy and comfort. The ensuite bathrooms boast luxurious amenities, providing a spa-like experience for guests. Additionally, there are three elegantly appointed guest bedrooms, sharing two hallway full bathrooms, ensuring all guests have a comfortable stay. The finished basement offers additional living space, perfect for recreation and entertainment. Follow a magical path and descend a set of stairs to discover your own private beach, where you can relax on the sand, swim in the pristine waters, or enjoy aquatic adventures. A mooring is also available for easy access to boating and water sports. Conveniently situated next to public tennis courts, this rental property offers opportunities for outdoor recreation right at your doorstep. Whether you're a tennis enthusiast or simply enjoy staying active, you'll appreciate the convenience of having courts nearby. This waterfront rental property combines luxurious amenities, stunning natural beauty, and convenient access to outdoor activities, providing an idyllic retreat for relaxation and enjoyment. Located close to downtown Vineyard Haven's shops and restaurants, this property offers the perfect blend of tranquility and convenience.

Brand new construction on Oyster Pond. This property features five bedrooms including a primary ensuite on the first and second floors. There are two additional bedrooms on the second floor, one with two twin beds and one with a twin over full bunk. The fifth bedroom is a guest suite with additional living area above the three car garage. Guests can enjoy beautiful views of the pond throughout the home, as well as plenty of space both indoors and out for entertaining.

Welcome to your dream luxury rental property in Edgartown, where every detail has been meticulously crafted to provide the ultimate experience in upscale island living. Nestled in a quaint neighborhood of newly constructed homes close to downtown Edgartown and the pristine shores of South Beach, this property offers the perfect blend of convenience and tranquility. Enjoy easy access to the island's vibrant dining scene, charming boutiques, and sandy beaches, allowing you to fully immerse yourself in the relaxed coastal lifestyle of Martha's Vineyard. This expansive estate features six luxurious bedrooms, including two opulent primary suites, one on each floor, with private en suite bathrooms. Two guest bedrooms with their own en suite baths for added privacy, and two additional bedrooms that share a well-appointed bathroom. Each bedroom is elegantly furnished and equipped with plush bedding, ensuring a restful night's sleep for every guest. Entertain in style in the spacious dining area, which comfortably seats ten guests for memorable gatherings and intimate dinner parties. The gourmet kitchen is a chef's delight, boasting high-end appliances, sleek countertops, and two dishwashers for effortless cleanup after meals. The finished basement is a haven of entertainment, featuring a state-of-the-art home theater with a massive 100-inch TV, perfect for movie nights or watching the big game. A fully stocked bar invites guests to unwind, while a well-equipped gym and pool table provide opportunities for recreation and fitness. Step outside to discover a resort-style outdoor living space. Lounge by the heated pool and hot tub surrounded by lush landscaping. The top-of-the-line outdoor kitchen is equipped with premium appliances and ample seating, making it ideal for al fresco dining and entertaining. Guests can unwind after a day at the beach by the outdoor fire pit. The property also boasts a stylish pool house, offering additional accommodations for guests or a secluded retreat for relaxation. Complete with its own bathroom, TV and fireplace, the pool house provides the ultimate in comfort and convenience. Enjoy seamless entertainment throughout the property with surround sound speakers installed throughout the property, creating an immersive audio experience for music, movies, and more. From the heated pool and hot tub to the meticulously landscaped grounds, every aspect of this property exudes luxury and sophistication. Whether you're lounging poolside, exploring downtown Edgartown, or soaking up the sun at one of the islands many beaches, this exquisite rental property offers an unparalleled retreat for discerning travelers seeking the ultimate Martha's Vineyard experience.