Vacation rentals in Oak Bluffs Harbor

Guest suite in Oak Bluffs

A spacious living room is highlighted by a large grey sectional couch adorned with various throw pillows. A wooden coffee table sits in front, featuring storage compartments. Two abstract paintings in calming blues are displayed above the couch, while soft lighting illuminates the area.

Lovely 2 BR Oak Bluffs Apartment

*To returning guests: Airbnb has restructured their fees; so while our nightly price may look higher at first glance, it is our same pricing overall This private apartment is on the 1st floor of a family home with a personal entrance & parking; owners and their son live upstairs. There are no shared spaces. It is a mile from Oak Bluffs Center, a half mile from the Cottages and Farm Neck Golf Course, and across the street is a bike path. The bus stop is on the corner for easy island wide travel!

FamilyValueOutdoor spaces

4.95 out of 5 average rating, 442 reviews

Guest suite in Oak Bluffs

An aerial view highlights a shoreline featuring sandy beaches and a long wooden pier extending into calm blue waters. Surrounding the area are residential homes and green landscapes, with boats visible on the water. The clear sky and vibrant hues create a scenic coastal environment.

Sea View Waterfront Beachfront Apartment

Prime location- right across the street from a sandy beach, a few minutes walk to the harbor, downtown, and transportation (boat, bus, etc). This beautiful street-level one-bedroom apartment sits across the street from the ocean, where you can take a dip and enjoy the beach. The apartment was recently redone and has a small bedroom with a queen size bed, small bathroom, full kitchen, and living room area with pull-out couch. Convenient to take the ferry into Oak Bluffs and walk to the apartment

FamilyValueBiking

4.97 out of 5 average rating, 141 reviews

4.98 out of 5 average rating, 105 reviews

Arrowsmith Cottage-Oak Bluffs Near Eastville Beach

Welcome to Arrowsmith Cottage! If you are considering bringing your small dog, please first contact me (scroll down on the cottage's listing page and click on the "Contact Host" button), and tell me a little bit about him/her, as dogs require homeowner's written approval and guest’s agreement to the pet fee and homeowners’ pet rules. We cannot allow cats, birds, or any animals other than one pre-approved dog. Hosts are not responsible for listing inaccuracies due to Airbnb's own input or AI.

FamilyLocationCheckout

4.96 out of 5 average rating, 102 reviews

The extended front porch features comfortable outdoor seating, including a patterned couch and a hanging chair. A striped runner runs along the wooden floor, while the street below reflects the vibrant town with shops and parked cars in view.

Apartment in Oak Bluffs

Cozy 3 bedroom apartment with King bed on Main St.

A 3 min walk to parks, beaches, the Oak Bluffs ferry and public transportation. Located in the middle of all Oak Bluffs has to offer. This apartment sits above Circuit Ave with a large extended front porch overlooking the town. You are only steps away from numerous restaurants, coffee shops, grocery stores and gift shops. A couple of blocks away is Niantic Park, home to 2 basketball courts, 3 tennis/pickleball courts and a playground. Directly behind you are the famous Gingerbread houses.

LocationFamilyCleanliness

4.9 out of 5 average rating, 155 reviews

A bright living space is visible, with sheer white curtains framing sliding glass doors that open to a private porch. A table with six chairs is seen under a vibrant pink umbrella, providing outdoor seating options for guests.

Cottage in Oak Bluffs

East Chop Cottage - walk to lighthouse & beach!

This quaint little cottage is located in the heart of East Chop, a neighborhood of Oak Bluffs. East Chop features the high, prominent bluffs that gave Oak Bluffs its name. A lighthouse, East Chop Light, stands at the north end of the chop on Telegraph Hill- only a five minute walk from the cottage. The cottage is a twelve minute walk to the harbor, and about a mile from the Oak Bluffs ferry! There is a public beach about 1/2 mile down the road. ***This space is not suitable for children

LocationFamilyQuiet

A charming cottage is framed by a lush garden with vibrant flowers. The front porch features two rocking chairs, inviting relaxation. Soft lighting emanates from inside, through the gothic-style windows, under a welcoming blue roof surrounded by greenery.

4.92 out of 5 average rating, 213 reviews

impeccable cottage STEPS to downtown OB & beach!

Unique opportunity to stay in an impeccable cottage in Downtown Oak Bluffs. With a front porch with rocking chairs, a back deck & grill, & an outdoor shower, and A/C! - this is the ideal oasis for your Vineyard Vacation. Turn right and find yourself steps from restaurants & shops on Circuit ave. Turn left and walk 5 mins to beautiful beaches. Everything you want out of vacation at your fingertips. Relax, and truly experience the Vineyard the way it was meant to be, at the @WeePackemInn

ValueFamilyOutdoor spaces

An open-living area showcases a dining table with transparent chairs and a modern chandelier above. A cozy seating arrangement with a sofa and colorful cushions is visible. Light enters through multiple windows, illuminating the space and enhancing the white shiplap walls.

4.97 out of 5 average rating, 39 reviews

1/2 mile walk to Downtown Oak Bluffs

Fully renovated home in Oakbluffs, just minutes from Downtown Oak Bluffs & beaches. It boasts three inviting bedrooms and a built in daybed/trundle bed living room cove. This home comfortably accomodates up to ten guests. The open kitchen, dining, living area serves as an ideal gathering space, and a comfortable area to relax after a day of exploring. Our newly renovated kitchen is equipped with brand new appliances and all the essentials you need to prepare delicious meals .

ValueFamilyNearby

4.96 out of 5 average rating, 45 reviews

An aerial view captures the layout of the neighborhood with various rooftops, showcasing a mix of architectural styles. The ocean is visible in the background, providing a scenic backdrop, while green spaces are located nearby, creating a serene environment.

Apartment in Oak Bluffs

14D Kennebec THE center of OB! No car, No problem!

An incredible stay awaits you in these new, luxury one-bedroom apartments right in the heart of town! Just steps from the Flying Horses Carousel, 100 steps from Back Door Donuts, and with Inkwell Beach Just a short walk across Ocean Park! All ferries and buses are nearby. Enjoy modern amenities like fast WiFi, full-size washer/dryer, smart TVs, and premium finishes. Don’t miss out on the best location in Oak Bluffs! Book now and experience unforgettable magic!

LocationValueBathroom

A rustic cottage with weathered gray siding is set against a backdrop of calm ocean waters. Wildflowers in vibrant yellow, pink, and purple line a dirt path, bordered by a wooden fence, offering a glimpse of the natural beauty surrounding the property.

4.88 out of 5 average rating, 41 reviews

The Boat House

Located on majestic East Chop and only a mile and a half from both Vineyard Haven and Oak Bluffs, this rustic ocean front cottage offers a unique Martha's Vineyard experience. Whether you relax on the the private beach and watch majestic sunsets, stroll up to East Chop Lighthouse, or head only a little over a mile to vibrant Oak Bluffs harbor, you are sure to have a memorable trip. This is the perfect perfect haven from which to explore Martha's Vineyard.

FamilyValueGrill

The exterior of the yurt showcases a circular wooden structure with large, rounded windows, complemented by a metal roof. A private yard features lush greenery, colorful flora, and outdoor seating arrangements, creating an inviting space for relaxation and outdoor activities.

4.93 out of 5 average rating, 327 reviews

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

ValueLocationGetting around

An open-concept living area features a spacious, light-filled layout with modern furnishings. A comfortable sofa is positioned opposite a wall-mounted television. Bar stools are arranged along an island with sleek finishes, enhancing the inviting kitchen space. Natural wood flooring complements the neutral decor.

4.96 out of 5 average rating, 25 reviews

Charming 3-Bedroom Home in the Heart of Oak Bluffs

Welcome to your perfect Martha’s Vineyard getaway! Nestled in the heart of Oak Bluffs, this charming 3-bedroom home offers the ultimate convenience and comfort. Located just above Sunset Park, you'll be steps away from Oak Bluffs Marina, Circuit Avenue, Inkwell Beach, East Chop Beach, the Campground, and Ocean Park. With easy access to State Beach and the surrounding towns, this is the ideal home base for your island adventure.

FamilyValueKitchen

A spacious, newly constructed home is showcased with a dark blue exterior and white accents. The façade features a prominent front porch with chairs and a large garage. A gravel driveway leads to the entrance, framed by a lush green lawn and trees.