Oak Bluffs
.jpg)
https://sandpiperrental.icnd-cdn.com/images/resorts/OB1.jpg
https://sandpiperrental.icnd-cdn.com/images/resorts/OB.jpg
https://sandpiperrental.icnd-cdn.com/images/resorts/Craft-1-2.jpg
https://sandpiperrental.icnd-cdn.com/images/resorts/DJI_0251_hdr (1).jpg
https://sandpiperrental.icnd-cdn.com/images/resorts/Inkwell Drone .jpg
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!
125 properties available
Enjoy high end living, with commanding water views in this luxurious and meticulously detailed home with guest house. This home is filled with artwork, beautifully restored architectural detail, and incredible water views. The main house includes four bedrooms, split between two floors, while the one bedroom guest house includes a full kitchen, liv
Oak Bluffs 8154
Enjoy high end living, with commanding water views in this luxurious and meticulously detailed home with guest house. This home is filled with artwork... Read More
Enjoy high end living, with commanding water views in this luxurious and meticulously detailed home with guest house. This home is filled with artwork... Read More
Centrally located, custom colonial, in Oak Bluffs. Cook a true Vineyard feast from the wonderfully designed chef's kitchen with Wolf Gas stove. The kitchen flows seamlessly into the living area where you may eat at the dining table that looks out to the back yard. Or for those evening cookouts, the rear deck is perfect. For those "working" on va
Oak Bluffs 832
Centrally located, custom colonial, in Oak Bluffs. Cook a true Vineyard feast from the wonderfully designed chef's kitchen with Wolf Gas stove. The k... Read More
Centrally located, custom colonial, in Oak Bluffs. Cook a true Vineyard feast from the wonderfully designed chef's kitchen with Wolf Gas stove. The k... Read More
This stunning single-level condo, situated on the second floor of the Seaview Condo complex, boasts two bedrooms and two bathrooms, along with a small additional room featuring a convenient desk. Perfectly positioned just across from the picturesque Inkwell beach and a leisurely stroll away from the charming Village of Oak Bluffs, this property is
Oak Bluffs 8025
This stunning single-level condo, situated on the second floor of the Seaview Condo complex, boasts two bedrooms and two bathrooms, along with a small... Read More
This stunning single-level condo, situated on the second floor of the Seaview Condo complex, boasts two bedrooms and two bathrooms, along with a small... Read More
Step back in time with a stay in this 1850s Victorian-style home, nestled in the heart of downtown Oak Bluffs. Overlooking the scenic Ocean Park and Nantucket Sound, this charming property offers the perfect blend of historic elegance and modern convenience. With seven bedrooms—one on the first floor and six on the second. On this floor is another
Oak Bluffs 8163
Step back in time with a stay in this 1850s Victorian-style home, nestled in the heart of downtown Oak Bluffs. Overlooking the scenic Ocean Park and N... Read More
Step back in time with a stay in this 1850s Victorian-style home, nestled in the heart of downtown Oak Bluffs. Overlooking the scenic Ocean Park and N... Read More
Sparkling Vineyard reverse level cottage has the fresh airy updates with painted white shiplap for wall decor, hardwoods and stainless steel to complete this modern beach house. From the open floor plan of dining, living and kitchen with walk out to the deck enjoy entertaining and keeping everyone together all on the second floor as well as a half
Oak Bluffs 8011
Sparkling Vineyard reverse level cottage has the fresh airy updates with painted white shiplap for wall decor, hardwoods and stainless steel to comple... Read More
Sparkling Vineyard reverse level cottage has the fresh airy updates with painted white shiplap for wall decor, hardwoods and stainless steel to comple... Read More
Experience the charm of Oak Bluffs in our delightful 2-bedroom cottage, perfectly situated in the heart of downtown. Both bedrooms, located on the second floor, feature en-suite bathrooms for your convenience. With A/C mini-split units in the living area and both bedrooms. Forget the hassle of needing a ferry reservation —this cottage is within wa
Oak Bluffs 8167
Experience the charm of Oak Bluffs in our delightful 2-bedroom cottage, perfectly situated in the heart of downtown. Both bedrooms, located on the sec... Read More
Experience the charm of Oak Bluffs in our delightful 2-bedroom cottage, perfectly situated in the heart of downtown. Both bedrooms, located on the sec... 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
This affordable and well-maintained four-bedroom Cape is located approximately two miles from the center of Oak Bluffs and just a short distance from the town landing on Lagoon Pond. It is ideal for accommodating your extended family. The efficient kitchen provides access to the back deck, perfect for outdoor dining and gatherings. The home feature
Oak Bluffs 877
This affordable and well-maintained four-bedroom Cape is located approximately two miles from the center of Oak Bluffs and just a short distance from ... Read More
This affordable and well-maintained four-bedroom Cape is located approximately two miles from the center of Oak Bluffs and just a short distance from ... Read More
This centrally air conditioned four bedroom traditional style home is located within the Bayes Hill neighborhood. A spacious, quiet and well maintained area in Oak Bluffs with beautiful curb appeal. This property has a well equipped kitchen, spacious living area, deck, and an area for those who need to work from home. There is an enclosed outdoor
Oak Bluffs 8101
This centrally air conditioned four bedroom traditional style home is located within the Bayes Hill neighborhood. A spacious, quiet and well maintai... Read More
This centrally air conditioned four bedroom traditional style home is located within the Bayes Hill neighborhood. A spacious, quiet and well maintai... 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
Five-bedroom Cape centrally located in Oak Bluffs. The main house has been beautifully appointed, including an open kitchen, dining, and a living area
with vaulted ceilings. The living area offers an oversized flat-screen TV and wood-burning fireplace leading into the Dining area, which opens up onto the back deck and pool area. The primary bedroo
Oak Bluffs 8116
Five-bedroom Cape centrally located in Oak Bluffs. The main house has been beautifully appointed, including an open kitchen, dining, and a living area... Read More
Five-bedroom Cape centrally located in Oak Bluffs. The main house has been beautifully appointed, including an open kitchen, dining, and a living area... Read More
A classically styled, expanded Cape in the Preserve in Oak Bluffs. Perched on a knoll overlooking the pond, this sprawling home includes a great room with vaulted ceilings, kitchen, living and dining area with French doors that open to an expansive patio and pool. Separate wings on each side of the great room house another living/sitting room and p
Oak Bluffs 8134
A classically styled, expanded Cape in the Preserve in Oak Bluffs. Perched on a knoll overlooking the pond, this sprawling home includes a great room ... Read More
A classically styled, expanded Cape in the Preserve in Oak Bluffs. Perched on a knoll overlooking the pond, this sprawling home includes a great room ... Read More
Tell us what you're looking for and someone will contact you with available options.
