luxury houses for rent Oak Bluffs, 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

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

Vacation in this Spectacular Oceanfront Estate in Falmouth with a private beach on Vineyard Sound. Walls of over-sized windows and sliders provide beautiful ocean views from nearly every room in the home. This custom built contemporary is impeccable, has over 6,000 sqft of living space, and offers 3 floors of living with 2 extraordinary Master Bedroom ensuites with private sitting areas. The home is equipped with an elevator to access second and third floor bedrooms. There are numerous gathering areas for relaxing and entertaining inside the home, and there are tiers of private exterior balconies and decks that wrap around the home to relax in the sun or shade and take in the beautiful vistas. Swim, paddle board, and kayak off of the sandy white beach at your back door. Both Master bedrooms have king size beds, bedrooms 3 and 4 have Queen sized beds, and the 5th bedroom has 2 twin beds. There is a terrific BBQ grill and large yard for cookouts. This home is located in close proximity to downtown Falmouth for shopping, restaurants, and ferry to Martha's Vineyard. Rental Terms: Other / Short Term - Two weeks: $40,000

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

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 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.

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.

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

Escape to this perfect waterfront Cape Cod summer rental getaway that has been newly renovated. Enjoy beautiful water views and a private dock with direct access to Vineyard Sound—no bridges required—this home is a boater's paradise. Dock your boat at the deep-water dock and soak in breathtaking sunsets from the west-facing deck. Not a boater, use the dock to launch a kayak or a float. The main level features a spacious primary suite, while the open-concept living area and modern kitchen create a seamless flow for relaxation and entertainment. Upstairs, you'll find two generous bedrooms and a beautifully updated tiled bath. The lower-level walk-out offers extra space for guests, ensuring comfort for all. Enjoy sun-soaked days at the association beach, just a short stroll away, or rinse off in the outdoor shower after a day on the water. Stay cool with split AC units throughout the home. Whether you're seeking adventure or serenity, this wonderful rental is your gateway to coastal living. Ready to set sail on a dream vacation? Book your stay today! Rental Terms: Summer Weekly: $6,000 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

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

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

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

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

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

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

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

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

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