Martha's Vineyard Vacation Rentals
650 properties available
Tucked away on 20 acres along the shores of Vineyard Sound, Chip Chop is one of Martha's Vineyard's most iconic and storied properties. Originally built in the 1940s for Broadway star Katharine Cornell, this extraordinary beachfront compound has welcomed generations of notable guests from the worlds of theater, film, literature, and politics. Surro
Vineyard Haven 907
Tucked away on 20 acres along the shores of Vineyard Sound, Chip Chop is one of Martha's Vineyard's most iconic and storied properties. Originally bui... Read More
Tucked away on 20 acres along the shores of Vineyard Sound, Chip Chop is one of Martha's Vineyard's most iconic and storied properties. Originally bui... Read More
A spectacular compound on the corner of South Summer Street and Captain's Walk, a private way which connects South Summer and South Water Streets, and five minutes to Main Street, and all of the best shops and restaurants. Offering five ensuite bedrooms, including a private bedroom and bath in the carriage house, the main house features a large gre
Edgartown Downtown 173
A spectacular compound on the corner of South Summer Street and Captain's Walk, a private way which connects South Summer and South Water Streets, and... Read More
A spectacular compound on the corner of South Summer Street and Captain's Walk, a private way which connects South Summer and South Water Streets, and... Read More
A short way down a quiet road, a sparkling white-shell driveway beckons...Pergolas wrapped in lush foliage - it has a feel of a tropical oasis with the comforts of home. The reverse level, open floor plan design allows for ease of entertaining, the spaces flow seamlessly into one another, sliders opening to the second-floor deck, overlooking the po
Edgartown Katama 724
A short way down a quiet road, a sparkling white-shell driveway beckons...Pergolas wrapped in lush foliage - it has a feel of a tropical oasis with th... Read More
A short way down a quiet road, a sparkling white-shell driveway beckons...Pergolas wrapped in lush foliage - it has a feel of a tropical oasis with th... Read More
Simply stunning new construction in a quiet new neighborhood just outside Edgartown Village. Exquisitely decorated by a leading designer, this home is a show-stopper. Not a detail has been overlooked. From the moment you walk in the front door, you will feel that this home is something special. With over five thousand square feet of space, you and
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Edgartown 530
Simply stunning new construction in a quiet new neighborhood just outside Edgartown Village. Exquisitely decorated by a leading designer, this home is... Read More
Simply stunning new construction in a quiet new neighborhood just outside Edgartown Village. Exquisitely decorated by a leading designer, this home is... Read More
Located in an exclusive Chilmark neighborhood, this home offers privacy and breathtaking views of the North Shore. This well-appointed 4 bedroom cottage has 2 bedrooms on the first floor and 2 on the second floor. Enjoy the expansive deck along the entire back of the house and dine al-fresco. The open area dining, living and kitchen spaces are the
Chilmark 2002
Located in an exclusive Chilmark neighborhood, this home offers privacy and breathtaking views of the North Shore. This well-appointed 4 bedroom cotta... Read More
Located in an exclusive Chilmark neighborhood, this home offers privacy and breathtaking views of the North Shore. This well-appointed 4 bedroom cotta... Read More
Step into your next island getaway at this beautifully remodeled 5 bedroom Vineyard Haven home, thoughtfully designed for comfort, style and entertaining. The first floor offers living and dining space and a sparkling white kitchen with stainless appliances. The first of five bedrooms is also on the first floor with an en suite. Upstairs are 3 addi
Vineyard Haven 1274
Step into your next island getaway at this beautifully remodeled 5 bedroom Vineyard Haven home, thoughtfully designed for comfort, style and entertain... Read More
Step into your next island getaway at this beautifully remodeled 5 bedroom Vineyard Haven home, thoughtfully designed for comfort, style and entertain... Read More
A beautiful interpretation of a charming Edgartown home in a quiet neighborhood - with glimpses of Edgartown harbor and all of the charm of downtown. The first floor is an open concept with a beautiful kitchen and large center island, marble countertops and stainless steel appliances. The kitchen opens to a chic dining area and living space with ga
Edgartown Downtown 28
A beautiful interpretation of a charming Edgartown home in a quiet neighborhood - with glimpses of Edgartown harbor and all of the charm of downtown. ... Read More
A beautiful interpretation of a charming Edgartown home in a quiet neighborhood - with glimpses of Edgartown harbor and all of the charm of downtown. ... Read More
Welcome to your perfect Oak Bluffs getaway! This inviting 4-bedroom, 3-bath home is located in the heart of downtown and comfortably sleeps up to 10 guests, with central air conditioning throughout for a cool, relaxing stay. Designed for easy vacation living, the home features a well-equipped kitchen and a spacious living room with plenty of seatin
Oak Bluffs 8075
Welcome to your perfect Oak Bluffs getaway! This inviting 4-bedroom, 3-bath home is located in the heart of downtown and comfortably sleeps up to 10 g... Read More
Welcome to your perfect Oak Bluffs getaway! This inviting 4-bedroom, 3-bath home is located in the heart of downtown and comfortably sleeps up to 10 g... Read More
Serenity at its best! This beautifully appointed property in Makonikey in West Tisbury offers scenic views and a private setting. A kitchen with a view is perfect for those looking to prepare a light meal to enjoy in the summer sun with easy access to an outdoor dining area. This dwelling sits on five acres of well-groomed land with an upper and lo
West Tisbury 1087
Serenity at its best! This beautifully appointed property in Makonikey in West Tisbury offers scenic views and a private setting. A kitchen with a vie... Read More
Serenity at its best! This beautifully appointed property in Makonikey in West Tisbury offers scenic views and a private setting. A kitchen with a vie... Read More
Originally built in 1810 as a farmhouse and later transformed into a bed and breakfast, this house is designed for the comfort of all family members. It has been thoughtfully renovated while preserving its architectural integrity, featuring old beams, wide pine floors, and decorative fireplaces that evoke a sense of nostalgia.
The five bedrooms ar
West Tisbury 1097
Originally built in 1810 as a farmhouse and later transformed into a bed and breakfast, this house is designed for the comfort of all family members. ... Read More
Originally built in 1810 as a farmhouse and later transformed into a bed and breakfast, this house is designed for the comfort of all family members. ... Read More
Location, Location, Location... Wonderful family compound in Katama with six bedrooms close to South Beach. You will feel like you are coming home when you drive into this private expansive Katama property. The main entrance opens up to a lovely living room which opens to an inviting three season sunroom offering a quiet sitting area to relax an
Edgartown Katama 590
Location, Location, Location... Wonderful family compound in Katama with six bedrooms close to South Beach. You will feel like you are coming home w... Read More
Location, Location, Location... Wonderful family compound in Katama with six bedrooms close to South Beach. You will feel like you are coming home w... Read More
A relaxing vacation awaits at this modern home overlooking the Lagoon. Tucked off of Barnes Road, the open concept layout offers stunning waterviews from the living, kitchen and dining areas, opening to a large outdoor deck. There is an ensuite bedroom on the main level and three additional bedrooms on the lower level as well as a media room with 6
Oak Bluffs 8104
A relaxing vacation awaits at this modern home overlooking the Lagoon. Tucked off of Barnes Road, the open concept layout offers stunning waterviews f... Read More
A relaxing vacation awaits at this modern home overlooking the Lagoon. Tucked off of Barnes Road, the open concept layout offers stunning waterviews f... Read More
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