Oak Bluffs
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Oak Bluffs - or 'OB' - is a classic beach town, filled with tons of fun! Enjoy the sandy beaches along the calm waters of Nantucket Sound, events held in Ocean Park and the Tabernacle, and the casual atmosphere of the harbor and Circuit Avenue. Popular attractions include the Flying Horses Carousel, the nation’s oldest operating platform carousel, and the Martha’s Vineyard Camp Meeting Association, a National Historic Landmark and community of over 300 charming Victorian gingerbread cottages surrounding a beautiful iron Tabernacle. Circuit Avenue is always bustling and has something for everyone – ice cream, coffee shops, eateries, bars and boutiques. The Harbor is entirely walkable and is a great place to relax and watch the boats coming and going. Outside of the downtown area, there are many areas in OB that offer a quieter atmosphere. Contact us and we'll help you find the perfect getaway!
124 properties available
Nestled on 1.5 private, wooded acres in Hidden Cove, this beautifully appointed multi-level home offers an ideal blend of tranquility and space for gathering. The open living and dining areas create a welcoming atmosphere, while the thoughtful layout provides quiet retreats for guests. The home sleeps seven and features three bedrooms and four and
Oak Bluffs 8013
Nestled on 1.5 private, wooded acres in Hidden Cove, this beautifully appointed multi-level home offers an ideal blend of tranquility and space for ga... Read More
Nestled on 1.5 private, wooded acres in Hidden Cove, this beautifully appointed multi-level home offers an ideal blend of tranquility and space for ga... Read More
Welcome to this charming three- bedroom property in Oak Bluffs, designed for comfort and relaxation. The primary bedroom is conveniently located on the first floor and features a king-sized en-suite bathroom with a rain shower. Upstairs, you'll find two additional bedrooms that share a hall bathroom.
The open floor plan seamlessly connects the kitc
Oak Bluffs 8173
Welcome to this charming three- bedroom property in Oak Bluffs, designed for comfort and relaxation. The primary bedroom is conveniently located on th... Read More
Welcome to this charming three- bedroom property in Oak Bluffs, designed for comfort and relaxation. The primary bedroom is conveniently located on th... Read More
Comfortable and conveniently located just one mile from downtown and Inkwell Beach, this three-bedroom home is the perfect island getaway. The primary bedroom features a private half bath, while the two additional bedrooms share a full hall bath. Enjoy a bright living area, fully equipped kitchen, and spacious deck for outdoor dining and relaxation
Oak Bluffs 8128
Comfortable and conveniently located just one mile from downtown and Inkwell Beach, this three-bedroom home is the perfect island getaway. The primary... Read More
Comfortable and conveniently located just one mile from downtown and Inkwell Beach, this three-bedroom home is the perfect island getaway. The primary... Read More
Looking for a cozy and inviting house for rent in Oak Bluffs? This beautiful property is located just a mile and a half from the beach, making it the perfect place for a family vacation or a getaway with friends.
With four spacious bedrooms and two well-appointed bathrooms, this house can comfortably accommodate up to eight guests. The bedrooms are
Oak Bluffs 8028
Looking for a cozy and inviting house for rent in Oak Bluffs? This beautiful property is located just a mile and a half from the beach, making it the ... Read More
Looking for a cozy and inviting house for rent in Oak Bluffs? This beautiful property is located just a mile and a half from the beach, making it the ... Read More
The "Preserve" off County Road at its finest! Five modern bedrooms, fully air conditioned, expanded farmhouse with inspiration and fixtures from Restoration Hardware and Waterworks. Modern design with soft tones of whites, ecru, and warm grays used throughout. Wide plank wood flooring, chevron wood floors in the kitchen, dining room, and den. The
Oak Bluffs 846
The "Preserve" off County Road at its finest! Five modern bedrooms, fully air conditioned, expanded farmhouse with inspiration and fixtures from Rest... Read More
The "Preserve" off County Road at its finest! Five modern bedrooms, fully air conditioned, expanded farmhouse with inspiration and fixtures from Rest... Read More
This beautifully renovated home, accommodating up to 10 guests, is located just minutes from Oak Bluffs, the vibrant hub of the harbor and village activities. For golf enthusiasts, Farm Neck Golf Club is only a half a mile away. The property features a large, nicely landscaped yard perfect for outdoor play, lounging, and dining, along with plenty o
Oak Bluffs 8802
This beautifully renovated home, accommodating up to 10 guests, is located just minutes from Oak Bluffs, the vibrant hub of the harbor and village act... Read More
This beautifully renovated home, accommodating up to 10 guests, is located just minutes from Oak Bluffs, the vibrant hub of the harbor and village act... Read More
This neighborhood, with an Oak Bluffs address, is one of the best-kept secrets. It's located down a quiet road while still providing easy access to Oak Bluffs, Edgartown, West Tisbury, and other points up island. You'll find biking and walking trails nearby that connect to the State Forest bike path network.
The home features a thoughtful floor pla
Oak Bluffs 819
This neighborhood, with an Oak Bluffs address, is one of the best-kept secrets. It's located down a quiet road while still providing easy access to Oa... Read More
This neighborhood, with an Oak Bluffs address, is one of the best-kept secrets. It's located down a quiet road while still providing easy access to Oa... Read More
This beautifully appointed custom five-bedroom Gingerbread-style main house with a guest cottage is perfectly situated in the heart of Oak Bluffs—an ideal setting for your summer getaway. Thoughtfully updated, the home features a well-equipped kitchen, spacious dining area, and two comfortable first-floor sitting rooms. Enjoy your morning coffee on
Oak Bluffs Main and Guest House 8172
This beautifully appointed custom five-bedroom Gingerbread-style main house with a guest cottage is perfectly situated in the heart of Oak Bluffs—an i... Read More
This beautifully appointed custom five-bedroom Gingerbread-style main house with a guest cottage is perfectly situated in the heart of Oak Bluffs—an i... Read More
The charming five-bedroom gingerbread beach cottage is strategically located on Ocean Park in the center of Oak Bluffs. Bird's eye view of all that is happening in the village at your fingertips. This home is in a prime location for the annual fireworks and Illumination Night, which are held every August. It features two front decks, providing an i
Oak Bluffs 8124
The charming five-bedroom gingerbread beach cottage is strategically located on Ocean Park in the center of Oak Bluffs. Bird's eye view of all that is... Read More
The charming five-bedroom gingerbread beach cottage is strategically located on Ocean Park in the center of Oak Bluffs. Bird's eye view of all that is... Read More
Your Vineyard Vacation awaits at this cozy 3 Bedroom, 2 Bath Cape Cod Style home located in the Lagoon Heights neighborhood of Oak Bluffs. The newly renovated kitchen flows seamlessly to the spacious backyard, perfect for gathering with friends and outdoor dining. In addition to the kitchen and living area, the first floor offers a bedroom with a q
Oak Bluffs 8158
Your Vineyard Vacation awaits at this cozy 3 Bedroom, 2 Bath Cape Cod Style home located in the Lagoon Heights neighborhood of Oak Bluffs. The newly r... Read More
Your Vineyard Vacation awaits at this cozy 3 Bedroom, 2 Bath Cape Cod Style home located in the Lagoon Heights neighborhood of Oak Bluffs. The newly r... Read More
Easy breezy summer living in this fresh and beautifully renovated, airy cape. Designed with a relaxed modern vibe, this house forces you to have a relaxing vacation. A large chef's kitchen offers plenty of space for easy entertaining or organizing dinner for your beach picnic. The kitchen even has a dedicated beverage area and juice bar! The decor
Oak Bluffs 8170
Easy breezy summer living in this fresh and beautifully renovated, airy cape. Designed with a relaxed modern vibe, this house forces you to have a rel... Read More
Easy breezy summer living in this fresh and beautifully renovated, airy cape. Designed with a relaxed modern vibe, this house forces you to have a rel... Read More
Overlooking Sunset Lake and the harbor, this gorgeous custom home mimics the architecture and steps up the luxury! From the wrap around porch and front gazebo, your view starts with the park and pond and expands to the bustling harbor, creating an ever-changing vista. The August fireworks display, Grand Illumination and all the boating action of th
Oak Bluffs Main House 8019
Overlooking Sunset Lake and the harbor, this gorgeous custom home mimics the architecture and steps up the luxury! From the wrap around porch and fron... Read More
Overlooking Sunset Lake and the harbor, this gorgeous custom home mimics the architecture and steps up the luxury! From the wrap around porch and fron... Read More
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