luxury houses for rent Massachusetts, United States

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.

Set along the coveted Moshup Trail in Aquinnah, this exceptional island compound offers the ultimate Martha's Vineyard retreat, combining breathtaking ocean views, unparalleled privacy, and resort-style amenities across a beautifully landscaped property. The main residence features four spacious bedrooms and expansive living spaces designed to capture Aquinnah's natural beauty. Large windows and outdoor gathering areas frame sweeping ocean views, creating the perfect backdrop for unforgettable Vineyard sunsets. A separate two-bedroom guest house provides additional accommodations for extended family and friends, ensuring both comfort and privacy for larger groups. A private pool and spa invite leisurely afternoons under the sun, while a fully equipped home gym allows guests to maintain their wellness routine throughout their stay. Beyond the property, enjoy exclusive access to a private beach, where the pristine shoreline and tranquil Atlantic waters await just moments from your door. Whether you spend your days poolside, exploring Aquinnah's natural beauty, or gathering with loved ones to watch the ocean sunset, this Moshup Trail compound offers an extraordinary Vineyard experience in one of the island's most sought-after locations. A rare opportunity to enjoy luxury, privacy, and the best of Martha's Vineyard from a truly remarkable coastal estate.

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

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.

Coastal charm at its best. This home is a short stroll to Osterville Village and Dowses Beach, sits on an expansive lot with plenty of room for backyard play. A sizeable screened-in sun porch makes it an ideal space for indoor/outdoor summer living. The sunny, well-appointed kitchen with marble waterfall countertops, wine fridge, and gas range opens to a tastefully designed living room decorated in coastal blues and whites. Recently renovated, the home includes shiplap details, Serena & Lily accents, brass hardware throughout for a look that combines coastal charm with a modern touch. The first-floor master bedroom features a private deck and an adjacent bath. Two additional first-floor bedrooms include desks/home office areas. Upstairs the “bonus” room features two sections – a playful nautical-inspired hangout space equipped with TV, games, and seating and an additional sleeping area. The home offers three full bedrooms (and bonus sleeping space), a well-equipped kitchen, a living room, and so much more. Amenities:Central air, linens & towels provided, high-speed internet & cable tv, patio, outdoor shower. Sleeps six: one king, one full, and four twin. Barnstable Beach Pass Included. No smoking. No pets. Rental price does not include state, regional, local, or community taxes or fees. Seasonal rental rates upon request. Rental Terms: Summer Weekly: $6,500 Per Week

Welcome to Seasons by the Sea! This fully remodeled Osterville home offers four bedrooms, three and a half baths and all the outdoor living space for a perfect beach vacation. Located less than a mile from Osterville Village, Seasons by the Sea is a short distance to Joshua’s pond and only two miles to Dowses Beach. Enjoy breakfast on the spacious farmer’s porch or curl up on the couch with a good book. Head down to the pergola and fire pit after dinner and have a glass of wine or toast marshmallows for s’mores. Seasons by the Sea has all the amenities to make the most of your Cape vacation. The full sized outdoor shower and changing area is a great place to clean up after a long day at the beach. The house has a fully stocked laundry room with beach towels and premium beach accessories for your enjoyment, including a beach pass. The beautifully redesigned kitchen comes stocked and ready for you to prepare family meals for sharing at the banquet style kitchen table. Just off the kitchen is a spacious deck with a large table, umbrella and chairs. This provides the perfect spot to entertain family and friends while you cook steaks and burgers on the Weber Grill! Seasons by the Sea’s bedrooms are warmly decorated and come complete with new premium mattresses and high end linens. There are two king bedrooms (a master and a separate lower level king suite), one queen and a room with two double beds. All are apportioned with flat screen TVs on the wall. No pets or smoking. Rental Terms: Summer Weekly: $9,300 Per Week

Nestled in the heart of Osterville, 48 Bayview Circle offers the perfect Cape Cod getaway with timeless coastal charm and a relaxed, comfortable feel. This beautifully maintained home features inviting living spaces filled with natural light, a well-appointed kitchen, and thoughtfully designed bedrooms ideal for family and guests. Enjoy quiet mornings with coffee on the deck, afternoons at nearby beaches, and evenings dining in the village or relaxing at home after a day on the water. Conveniently located near Osterville Village, marinas, beaches, restaurants, and shopping, this home is the perfect retreat to experience all that Cape Cod has to offer. Amenities: Sleeps 6: 1 King, 1 Queen, 2 Twins | Barnstable Beach Pass | Central AC | Internet Rental Terms: Summer Weekly: $4,200 Per Week

Cape Cod summertime magic awaits at this classic shingled charmer in the heart of Wianno. Just moments from Osterville Village and Dowses beach, and superbly appointed, everything needed for carefree indoor/outdoor vacation living is here. A well-equipped kitchen flows seamlessly into the dining and seating area, opening up to a three-season room overlooking a bluestone patio with outdoor dining. The first floor primary bedroom with ensuite bathroom offers privacy and sanctuary. A second bedroom - also on the first floor - has an adjacent full bath. Upstairs offers additional sleeping space with two twin beds with trundles. Amenities: central air, linens and towels provided, high-speed internet, and patio. Sleeps six: one king, one queen, and two twins with trundles. Barnstable Beach Pass Included. No smoking. Rental Terms: Summer Weekly: $7,000 Per Week

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

Availability this summer at this beachfront home steps from Old Silver Beach. The house is located in Old Silver Beach Estates on the private, expansive white sandy beach. Enjoy the ocean breeze, and the glorious sunsets. The home is meticulously maintained, with room for eight people (4 bedrooms), and 3 ½ baths. Additionally, there is a spacious family room, kitchen with large dining area and den. The yard has plenty of room for your outdoor activities. This rare opportunity awaits. Amenities: Outdoor shower, A/C, Internet, linens, towels provided. Two week stay is $30,000 Rental Terms: Summer Weekly: $15,000 Per Week

Winter rental. Welcome to this beautifully renovated ranch in East Falmouth, the perfect Cape Cod getaway for families and friends. Thoughtfully updated throughout, the home features all-new furnishings, new appliances, and a charming deck for enjoying your morning coffee or evening relaxation. Sleeping up to 8 guests, this inviting home offers a large private backyard with plenty of room for outdoor fun, along with a classic Cape Cod outdoor shower to rinse off after a day at the beach. Conveniently located just minutes from Mashpee Commons, you'll enjoy easy access to shopping, dining, beaches, golf, and everything that makes Cape Cod a favorite vacation destination. Whether you're spending the day exploring Falmouth's beautiful coastline, enjoying time with family and friends in the backyard, or unwinding after a day of adventure, this delightful home is the perfect place to create lasting Cape Cod memories Rental Terms: Summer Weekly: $3,200 Per Week

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

Welcome to 147 Scudder Road in Osterville! This charming rental offers the perfect blend of convenience and relaxation, just a short stroll away from Main Street and the pristine shores of Dowses Beach. With its ideal location and cozy atmosphere, this is the perfect retreat for enjoying all Osterville offers. Amenities: Central Air, Wireless Internet, Cable TV, Outdoor Shower, Barnstable Beach Pass. Sleep: 5, two queens and one full. The rental price does not include state, regional, local, or community taxes or fees. Rental Terms: Summer Weekly: $4,800 Per Week

Ocean Front on Nantucket Sound. Five Bedrooms, four full baths. Fabulous views, steps to walk or swim on the beach. Outstanding rental - books quickly Rental Terms: Summer Weekly: $17,000 Per Week

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

Exclusive off season waterfront rental in Falmouth, available until June 1, 2026. Luxurious living in this exceptional 5-bedroom, 4-bath waterfront residence with deep-water dock and sweeping views of the saltwater harbor. Wake each morning to breathtaking sunrises, coffee in hand on your private covered porch, as boats glide by and the harbor comes to life. Designed for effortless luxury and relaxation, the home features upscale interiors that blend refined coastal charm with modern elegance. Sun-filled, spacious living areas invite gathering and entertaining, while the gourmet kitchen is perfectly appointed for culinary creations and hosting family and friends. Five serene bedrooms and four spa-inspired baths provide comfort and privacy, including three ensuite bedrooms with stunning water views. Every detail has been thoughtfully curated to create a tranquil, elevated retreat. Enjoy strolls on the private sandy association beach just moments away, explore the harbor by boat from your own dock, or venture into downtown Falmouth, the ferry to Martha's Vineyard, and local shopping and dining—all just minutes from your door. Rental Terms: Other / Short Term - Per Month Off Season: $12,000

Located in the lovely seaside Cape Cod village of Cotuit, this renovated, impeccable home features three bedrooms, two and a half baths and new laundry. Entertain in the sun filled brand new eat-in kitchen and large living room with fireplace. Enjoy one floor living with en-suite primary bedroom with sliders out to the deck and two other bedrooms and an office. The deck runs the entire length of the rear of the home and overlooks the private acre yard. Enjoy the convenient location close to shopping, restaurants, town docks and Nantucket Sound beaches. The popular Cotuit Kettleers baseball team games entertain folks of all ages just a short distance away. Other local activities include Cahoon Museum, Cotuit Center for the Arts and Kettle-Ho restaurant. What a wonderful place to enjoy your warm summer days and breezy nights. The pricing includes $800 per night for Memorial Day weekend, $5000 for June 1-27 and $6000 for June 27-July 31. Please contact agent for any other dates. Rental Terms: Summer Weekly: $5,000 Per Week

Escape to a relaxing, fun-filled vacation at this charming rental home located at 97 Sixth Ave, West Hyannisport. This well-appointed retreat is equipped with everything needed for a comfortable and memorable stay. Enjoy central air conditioning, provided linens and towels, high-speed internet, and cable TV. Refresh yourself in the outdoor shower after a day at the beach, and unwind on the spacious deck, perfect for outdoor dining and lounging. Beach chairs and beach towels are provided for your convenience. A Barnstable beach pass is included, offering easy access to beautiful local beaches. The home sleeps up to six guests with two cozy queen beds and two comfortable full beds. Please note that the rental price does not include state, regional, local, or community taxes or fees. Rental Terms: Summer Weekly: $3,400 Per Week

Just moments from Keyes Beach, this beautifully renovated three-bedroom, two-bath home perfectly balances modern coastal style with relaxed sophistication. Thoughtfully designed and exquisitely furnished, each bedroom features Matouk linens and Serena & Lily bedding for a luxurious night’s rest. The open-concept living areas flow effortlessly to a private outdoor oasis complete with a fire pit, hot tub, and dining area—ideal for summer evenings under the stars. Additional amenities include central air, high-speed internet, an integrated Sonos sound system, and premium linens and towels. Accommodations comfortably sleep six: two king bedrooms, one queen, and a daybed. Ideally located within walking distance of the Hyannis Yacht Club and just minutes from the Hyannisport Golf Club, this home offers easy access to downtown Hyannis, the harbor, boutique shopping, dining, and ferries to the Islands. Rental Terms: Summer Weekly: $6,000 Per Week

Experience the charm of a beautifully restored coastal antique in the heart of Centerville. Ideally located just minutes from Craigville Beach and a short 2-minute walk to the town dock, this home offers the perfect blend of seaside convenience and timeless character.Thoughtfully remodeled with privacy and comfort in mind, the home features stunning Serena & Lily–inspired décor throughout, creating a light, airy coastal feel. Property highlights include: 3 spacious bedrooms, 2 full baths Stylish, fully updated interiors Private outdoor oasis with hot tub Outdoor TV and inviting sitting area—perfect for relaxing or entertaining Peaceful setting with easy access to beaches, boating, and village amenities- Four Seas Ice cream, 1856 Country Store, Centerville Library & new playground This unique rental combines classic Cape charm with modern luxury—an ideal summer escape or year-round retreat. Rental Terms: Summer Weekly: $5,500 Per Week

This home is located in the heart of Wianno, only minutes to Dowses Beach and the village of Osterville. The first floor offers an open floorplan including living room, dining, kitchen, half bath, and a large master bedroom with ensuite bathroom. The second floor has three additional bedrooms and one large full bath. Fabulous outdoor space for entertaining. Amenities: Central Air, Outside Shower, Wifi, Cable TV, Linens & Towels Included. Barnstable Beach Pass Provided. No Smoking & Pets. Rental price does not include state, regional, local or community taxes or fees. Rental Terms: Summer Weekly: $7,500 Per Week

Your Luxury Cape Cod Vacation Awaits! Welcome to "Tranquility" 48 Grandview Drive, South Yarmouth, MA , a Harbor Haven waterfront retreat making its debut, offered at $17,500 per week as a summer rental. With 4 bedrooms (two Primary)and 5 baths, this beautifully renovated home is uniquely positioned to offer both sunrise and sunset views over the water—a truly special Cape Cod experience. Begin your mornings with coffee watching the sun rise, and end your evenings on the extra-large patio watching the sky glow at sunset—all from your own backyard overlooking the river. Spend your days with whatever Watersport you wish from your private dock (33' long x 6’) or your very own private tidal beach just outside your door on Bass River. Bring your own boat or rent one locally (happy to supply information on renting boats), enjoy immediate access to Bass River (speed zone) and beyond. Also perfect for sailing, kayaking, paddleboarding, and swimming. Guests also enjoy access to the Harbor Haven private association beach, perfect for swimming, sunbathing, and relaxed coastal afternoons. Thoughtfully designed for comfort and tranquility, this home captures the essence of luxury Cape Cod living with incredible views of Bass River. This is where summer memories are made! Rental Terms: Summer Weekly: $17,500 Per Week

Welcome to your ideal summer retreat at 360 Main St, Osterville. This exceptional property offers everything you need for a luxurious and relaxing stay. Enjoy the stunning outdoor amenities, including a sparkling pool, cozy fire pit, fully-equipped outdoor kitchen, and multiple seating areas perfect for entertaining. For sports enthusiasts, a private pickleball court awaits. Inside, the home boasts four beautifully appointed bedrooms, three full baths, and two half baths. The fabulous kitchen is a chef’s dream, and multiple living spaces provide plenty of room for everyone to unwind. Central air conditioning ensures comfort throughout your stay, and an office space offers a quiet retreat for work or reading. The property also features an outside shower for rinsing off after a day at the beach. A Barnstable Beach Pass is included, giving you access to the beautiful Dowses Beach. Located in the charming village of Osterville, you’ll be just minutes away from delightful restaurants, boutique shops, and everything you need for a perfect summer getaway. Experience the best of Cape Cod living at 360 Main St. Your summer escape awaits. No smoking. Rental price does not include state, regional, local, or community taxes or fees. Rental Terms: Summer Weekly: $16,000 Per Week

Spend your Cape Cod vacation in this magnificent property located on Garrison Lane in Osterville. Enjoy your days relaxing by the private pool surrounded by professionally landscaped grounds. Amenities: heated pool, central air, linens and towels provided, high-speed internet and cable tv, outdoor shower, spacious patio & screened-in porch. Sleeps: 8 four queen beds. Barnstable beach pass included. No smoking. Rental price does not include state, regional, local, or community taxes or fees. Rental Terms: Summer Weekly: $15,000 Per Week