Martha’s Vineyard, Massachusetts, has long been a treasured summer destination for Black travelers, with Oak Bluffs at the heart of the island’s Black travel history and community. This guide brings together bed and breakfasts, inns, and vacation rentals in Oak Bluffs and across the Vineyard.
Explore independently Black-owned lodging alongside homes in Getaway Society’s vacation-rental portfolio, a brand connected to East Chop Capital. Each listing includes location details, standout features, and booking information to help you plan a stay that fits your trip.
Black-Owned Bed & Breakfasts & Vacation Rentals in Oak Bluffs & Martha’s Vineyard
📱 Before you book—Check BlackHotelGuide.com First / Install the Black Hotel Guide app
Bed and Breakfasts, B&BS, on Martha’s Vineyard
Inkwell Beach House — Martha’s Vineyard. | BOOK
Just steps from one of the most culturally significant beaches in Black America, Inkwell Beach House places guests at the center of Vineyard history. This Black-owned vacation home offers both location and meaning, connecting travelers directly to Oak Bluffs’ storied past.
Why Stay Here: Stay where history lives—walkable, symbolic, and deeply rooted in Black Vineyard culture.
–BOOK
Narragansett House — Bed & Breakfast | BOOK
A longtime cornerstone of Oak Bluffs hospitality, Narragansett House is a historic Black-owned bed and breakfast that has welcomed generations of Vineyard visitors. Known for its gracious atmosphere and prime location, it remains a beloved option for travelers seeking tradition and connection.
Why Stay Here: Classic B&B hospitality with decades of Black travel history behind it.
–BOOK
The Oak Bluffs Inn — Bed & Breakfast | BOOK
The Oak Bluffs Inn is a Black-owned boutique bed and breakfast offering refined accommodations in the heart of town. Blending historic architecture with modern comforts, the inn is ideal for couples and travelers seeking a polished Vineyard stay.
Why Stay Here: Boutique charm, personalized service, and central Oak Bluffs access.
–BOOK
Beach houses, Vacation Rentals and Luxury Villas on Martha’s Vineyard & Oaks Bluffs
Soulas Martha’s Vineyard Victorian Beach House. | BOOK
Walk to Inkwell Beach & Town: Soulas Martha’s Vineyard Victorian Beach House is a grand Victorian home near Inkwell Beach and Circuit Avenue. Historically known as Akwaaba House, this property continues to be recognized for its place within Oak Bluffs’ Black-owned lodging landscape.
Why Stay Here: Spacious historic elegance in one of Oak Bluffs’ most walkable locations.
–BOOK
Pirate’s Cove — Oak Bluffs, Martha’s Vineyard | BOOK
Quintessential MV home near Oak Bluffs, beach & harbor: Pirate’s Cove is a Victorian-style vacation home on a quiet lane in East Chop. With four bedrooms, four bathrooms, and space for up to eight guests, it’s about a 15–18-minute walk from the beach, harbor, and Oak Bluffs town center.
The home features a large deck, backyard, hammock, gas grill, outdoor shower, and a finished basement with an arcade machine. Flexible twin beds, including one trundle, make it a practical choice for families and friends traveling together.
The property is part of Getaway Society’s luxury vacation rental portfolio. Getaway Society is affiliated with East Chop Capital, a Black-owned, multi-asset private equity and venture capital firm co-founded by Calvin L. Butts, Jr. and Carrington M. Carter.
Why Stay Here: A relaxed East Chop setting, walkable access to Oak Bluffs, and inviting indoor and outdoor spaces for an island stay.
–BOOK
Pirate’s Reef — Oak Bluffs, Martha’s Vineyard | BOOK
Pirate’s Reef is modern, luxury a five-bedroom, 4.5-bathroom w/full basement home in East Chop that accommodates up to 13 guests. The approximately 3,500-square-foot property has two master suites, a living room on each floor, and a finished basement with a wet bar and a combination pool and ping-pong table.
Tucked into a wooded setting behind historic Shearer Cottage, Pirate’s Reef offers a fire pit, gas grill, multiple Smart TVs, and parking for up to six cars. The beach, harbor, and Oak Bluffs town center are about a 15-minute walk away.
The property is part of Getaway Society’s luxury vacation rental portfolio. Getaway Society is affiliated with East Chop Capital, a Black-owned, multi-asset private equity and venture capital firm co-founded by Calvin L. Butts, Jr. and Carrington M. Carter.
Why Stay Here: Room for a larger group, separate gathering areas on both floors, and a peaceful East Chop location close to Oak Bluffs.
–BOOK
53 Carol Lane — Oak Bluffs, Martha’s Vineyard | BOOK
Located in a quiet residential pocket of Oak Bluffs, 53 Carol Lane is a Black-owned vacation rental offering guests a peaceful retreat with easy access to beaches, town attractions, and seasonal events. Ideal for families and groups, this home provides privacy while remaining close to the heart of Oak Bluffs.
Why Stay Here: A residential feel with Vineyard convenience, perfect for longer stays and repeat visitors.
–BOOK
Bird Street Breeze — Oak Bluffs, Martha’s Vineyard.| BOOK
Bird Street Breeze is a bright, Black-owned vacation home designed for relaxed island living. Situated near Oak Bluffs’ most popular beaches and attractions, this property offers a comfortable base for travelers who want walkability without sacrificing space.
Why Stay Here: Easy access to town, beaches, and nightlife with a laid-back, welcoming atmosphere.
–BOOK
Black Ivy Cottage — Direct Oceanfront | BOOK
With sweeping ocean views and direct waterfront access, Black Ivy Cottage stands out as a premier Black-owned Vineyard escape. This cottage blends coastal elegance with privacy, offering guests an elevated island experience right on the water.
Why Stay Here: Oceanfront living with style, serenity, and unmistakable Vineyard charm.
–BOOK
Dragonfly MV Properties — Dragonfly House — Oak Bluffs, Martha’s Vineyard | BOOK
Dragonfly House is a Black-owned vacation rental known for its warm design, comfortable layout, and proximity to Oak Bluffs attractions. Whether visiting with family or friends, this home provides an inviting setting for memorable island stays.
Why Stay Here: Comfortable, community-centered lodging close to the action.
–BOOK
Dragonfly MV Properties — Damselfly House | BOOK
Part of the Dragonfly MV collection, Damselfly House offers guests another thoughtfully curated Black-owned option in Oak Bluffs. Designed with relaxation and functionality in mind, it’s well-suited for extended stays and multi-generational travel.
Why Stay Here: A polished, dependable stay backed by experienced Black ownership.
–BOOK
Before you book—Check BlackHotelGuide.com First
➡️ Install the Black Hotel Guide app
Beyond Your Stay: Where Culture Meets Community
A Vineyard visit isn’t complete without engaging the island’s cultural and culinary landmarks.
- Edgartown Diner is a longtime favorite for classic comfort food and casual meals after a beach day or ferry arrival.
- The African American Heritage Trail of Martha’s Vineyard offers an essential journey through the island’s Black history, highlighting landmarks, stories, and community spaces that shaped Martha’s Vineyard into the destination it is today.
Why Booking Black-Owned on Martha’s Vineyard Matters
Choosing Black-owned lodging on Martha’s Vineyard is about more than accommodations—it’s about continuity. These homes, inns, and guesthouses help preserve the island’s cultural legacy while supporting present-day Black ownership in a market where representation matters.
When you stay Black-owned, you’re not just visiting the Vineyard—you’re participating in its living history.
Plan Your Stay
Explore all Black-owned lodging options on Martha’s Vineyard and Oak Bluffs at BlackHotelGuide.com and make your next trip one that reflects purpose, culture, and unforgettable island hospitality.
Looking for other destinations?
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