
Sankofa Vineyard Retreat is a Black-owned Oak Bluffs getaway offering a 4-bedroom, 2-bath main house that sleeps up to 9, plus a private 1-bedroom, 1-bath studio—available separately or together for a total of 5 bedrooms and 3 baths. Interested renters can inquire and connect directly with the owner through the Airbnb contact portal for seasonal availability. https://www.airbnb.com/rooms/1208074066306032389?guests=1&adults=1&s=67&unique_share_id=8c3efc3e-ddb1-4e14-98c9-d941a31f1e76 & https://www.airbnb.com/rooms/1203722448954188613?guests=1&adults=1&s=67&unique_share_id=389c5865-784e-473c-afed-9547cab27803

Legacy House is an elegant 5-bedroom, 3½-bath colonial in Vineyard Haven that sleeps up to 12 guests and offers over 4,000 sq ft of modern comfort. Built in 2020 and newly furnished in 2026, the home features individually controlled AC, a private fire pit, and generous indoor and outdoor living spaces—ideal for memorable Vineyard stays. 📩 Booking & Inquiries:
Guests can contact the owner directly through the We Need a Vacation contact portal. https://www.weneedavacation.com/Marthas-Vineyard/Vineyard-Haven-Vacation-Rental-41170

The Sandcastle – Vineyard Haven, Martha’s Vineyard 🌊✨
Imagine yourself here — beachfront bliss, ocean breezes, and pure luxury.
This 5BR, 6½-bath retreat sleeps 12 and features a private beach, deep-water dock, and modern coastal design made for unforgettable gatherings. Perfect for Juneteenth, July 4th, Labor Day, or a peaceful summer escape.
🌅 Luxury. Privacy. Restoration.
📍 Vineyard Haven, Martha’s Vineyard
🔗 Serious inquiries: https://www.weneedavacation.com/Marthas-Vineyard/Vineyard-Haven-Vacation-Rental-38942

The Encore House is a beautifully appointed Oak Bluffs property featuring a main cottage and a cozy garage apartment, perfect for couples, families, or groups seeking flexibility. Centrally located near the Martha’s Vineyard Performing Arts Center, it offers easy access to beaches, shopping, and dining. A peaceful retreat with the best of the Vineyard just minutes away.
Rent both the Cottage and the Garage Apartment for flexibility, privacy, and shared gathering space—while staying together in one prime location.
All inquiries & bookings must be made through the We Need A Vacation listing portal:
Charming & Centrally Located Oak Bluffs Garage Apartment (Listing #41194)
Charming and Centrally Located Oak Bluffs Cottage (Listing #41191)
Classic Vineyard charm. Central location. Thoughtful design.
Your Oak Bluffs stay starts here.
https://www.weneedavacation.com/.../Oak-Bluffs-Vacation.../ & https://www.weneedavacation.com/.../Oak-Bluffs-Vacation.../

Black-Owned • Trusted • High-Visibility
Soulas Martha's Vineyard Victorian Beach House Walk to Inkwell Beach & Town (Circuit Ave) Summer and Fall 2026 Dates Available! 5 Bedrooms 3 Full Bathrooms Flat Screen TVs Central Air Patio Private Driveway Book here: https://vrbo.onelink.me/ItNz/2v6awykj
Newly renovated, Great for Family & Friends, Corporate Retreats, Central Air & Heat, walk to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, Galley kitchen, new appliances, dining room, family room, Flat Screen TVs, FREE Wifi, washer & dryer, Oak & Pine wood flooring, outdoor shower, wrap around porch, blue stone patio, side backyard, private cobblestone driveway, comfortable beds, pillows and mattresses encased in (non-vinyl) water and allergen proof protectors. COVID-19-conscious cleaning and disinfecting are done regularly 5 Bedrooms 3 Full Bathrooms ◦ Living room ◦ Dining room ◦ Galley kitchen ◦ Family room ◦ Washer/Dryer ◦ Central Air and Heat on first floor ◦ Central Heat and Air Conditioning ◦ Patio/Courtyard ◦ Large wrap around porch ◦ Breakfast nook ◦ Flat screen TVs

https://oasison.my.canva.site/
This newly renovated 3-bedroom, 3-bath Oak Bluffs home sleeps up to 8 and is ideally located just minutes from the week’s signature events, beaches, restaurants, and all that Martha’s Vineyard has to offer.
Contact: Madeiramrealestate@gmail.com

https://studiorealty.com/properties/coastal-retreat-in-quiet-edgartown-neighborhood
Contact: Bridget Smith, 718 578-5886. Email: bridgeloveinc@aol.com

L Edgartown - Sunny Beach House on the Bike Path! AC! FREE Bus to town!
3 BR, 2 baths, Sleeps 6, Beds: 2 queens, 2 twins
Beach: 2 miles to State Beach; 3 miles to South Beach
This comfortable home is ideally situated on the bike path! Perfect for a family vacation, a romantic getaway or a small gathering of friends. It"s located midway between Oak Bluffs town center and Edgartown Village

Welcome to this Oak Bluffs Modern Cottage
2 bedrooms 2 beds, 1 bath, sleeps 4.
Walkable to downtown Oak Bluffs, Circuit Avenue, and The Inkwell Beach. This 2-story home has a modern kitchen & cozy living room. Relax on the outdoor patio & enjoy the BBQ grill. Two queen size beds make this home perfect for a small family, girls trip, or couples vacation. Maximum 4-person occupancy. July - August rentals minimum 7 days with a Saturday or Sunday check-in. Flexible check-in / out for multi-week stays. No Pets.
https://www.airbnb.com/rooms/23730119?viralityEntryPoint=1&s=76

First-timers to The Vineyard? I highly recommend a week in late August/early September, after all of the hoopla... when daily life becomes easier!
Cozy Cottage at Coleman Corners is nestled in a quiet, wooded area of East Chop, Oak Bluffs, but merely a 10-minute walk to downtown shopping, restaurants, art galleries, museums, beaches and a vibrant nightlife.
Quiet, comfy, cozy and warm.....your home away from home....the Cottage can accommodate 8 adults and 2 small children, with 4 Bedrooms, a Kids' Loft,
2 Bathrooms with Showers and an Outdoor Shower.
Or perhaps you can only spare a few nights: July 8, 9 and 10 are currently available.
FMI: Please see: https://joyner12.wixsite.com/cozycottage and inquire via website, if interested.

The Island Luxe Retreat at Tower Ridge is a spacious Oak Bluffs getaway located directly across from Farm Neck Golf Course, just minutes from beaches, town, and island attractions. This beautifully appointed home features 4 bedrooms, 3 full bathrooms, and comfortably sleeps up to 10 guests. Designed for relaxed island living, it offers open, light-filled spaces ideal for families or group stays. No pets.
👉 Interested renters can use the link below directly for availability, pricing, and inquiries:
https://www.vacasa.com/unit/123832
Nestled right in the heart of Oak Bluffs, this cozy garden suite is your perfect coastal escape for Legacy Week 2026. Step through your own private entrance into a bright, welcoming retreat just a short, sun-drenched stroll away from the vibrant energy of Circuit Avenue and the sandy shores of Inkwell Beach. It is the ultimate laid-back haven to unwind, soak up the Vineyard magic, and experience the best of the island right at your doorstep.
https://www.weneedavacation.com/Marthas-Vineyard/Oak-Bluffs-Vacation-Rental-39489/#section-pricing
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