Martha’s Vineyard holds a special place in Black travel history. For generations, the island—particularly Oak Bluffs—has been a cherished summer refuge for Black families, artists, professionals, and cultural leaders. From the legacy of Inkwell Beach to the tight-knit seasonal community that returns year after year, the Vineyard represents far more than a vacation destination—it’s a living archive of Black leisure, resilience, and joy.
Today, that legacy continues through a growing collection of Black-owned bed and breakfasts and vacation rentals that offer travelers authentic stays rooted in community, culture, and comfort. Below is a curated guide to where to stay when you want your Vineyard experience to reflect both excellence and intention.
Black-Owned Bed & Breakfasts & Vacation Rentals in Oak Bluffs & Martha’s Vineyard
53 Carol Lane — Oak Bluffs, Martha’s Vineyard
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.
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Bird Street Breeze — Oak Bluffs, Martha’s Vineyard
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
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.
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Dragonfly MV Properties — Dragonfly House — Oak Bluffs, Martha’s Vineyard
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
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.
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Inkwell Beach House — Martha’s Vineyard
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.
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Narragansett House — Bed & Breakfast
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.
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Soulas Martha’s Vineyard Victorian Beach House
Currently listed on major booking platforms, 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
The Oak Bluffs Inn — Bed & Breakfast
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
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.