Vacation rentals with breakfast in Oak Bluffs

Oak Bluffs/ Harbor Views/ Queen Bed/ In Town

Welcome to Watchaboat! Our family home has a comfortable, clean room available. The room has a beachy cottage feel where you'll be happy to rest at the end of a summer day. We've got a great location, overlooking Oak Bluffs harbor, a 9-minute walk to downtown OB & a quick stroll to Oak Bluffs Town Beach (.3 mile). Our bustling home has a busy business on the property, so it's fit for travelers who need to drop their bags & go enjoy the island. Please read the listing carefully before booking!

Step Away; A Martha's Vineyard Retreat

Studio apartment addition attached to our family home. Our home is located three miles to downtown Edgartown with bus service & bike path close by. Private entrance, mini fridge, coffee press & accessories, private bath with shower, washer/dryer, bed in a loft area (ladder access only) with queen size sofa bed available below for additional sleeping. This is our family home with two baby boys. We try our best to keep quiet, but it is important to note their presence; rental has a sound machine.

Edgewater Sanctuary | Fully Off Grid | On The Bay

Welcome to "Edgewater Sanctuary", a part of the "Edgewater Escapes" collection of properties. This brand-new off-grid house sits on a uniquely secluded point directly on Buzzards Bay. 100% solar powered with breathtaking ocean views from every room. Kayak and fish from the front yard, relax on the screened porch, or gather around the fire under the stars. With 3 bedrooms, 1.5 baths, and space for 7 guests, it’s the perfect escape for those seeking unrivaled seclusion and connection with nature.

The Alison Boylston Piazza House

Welcome to my home, a 200 year-old former whaling captain's home in the heart of historic Edgartown on Martha's Vineyard (not Nantucket). From here, every amenity - shops, beaches, harbor, restaurants, and night life - is accessible by foot or bicycle. No car needed. ***IMPORTANT***the price listed is for the main double guest room that has one queen-sized bed. There is an additional charge for the second, single room ($100). To book two separate beds you must specify 3 people in your party.

North Falmouth Suite 'downstairs suite'

This gueen-bed suite has a private entrance, a living room with wifi/tv, and a small, private bath, on a beautifully maintained property on 28A in N. Falmouth. Enjoy easy access to beaches & the bike path is across the street. The suite is priced based on two people, additional people - older kids, friends, are $40/night more; two twin blow-ups can be set up in living room. You must list the total amount of guests when booking. This house is not well suited to toddlers & young children.

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

New Seabury French Chateau Inspired

You will love this bright, sunny, safe, quiet and fully fenced New Seabury home for home away getaway and relaxation. Split floor plan with master bedroom and bath on one side of the home, while there are two other bedrooms which share a bath on the other side. All bedrooms are large enough to accommodate family of 10! Additional living space in the loft as well as a bedroom and bath in the basement. Less than a mile away from the beach, lots of beautiful trails and more!

West Chop Cottage + Beach Access

Sweet, rustic, and tiny - yet comfortable with all the amenities - the cottage is a short walk to the town center, lighthouse, landmarks, and lovely harbor beaches on desirable West Chop. The private yard with harbor view allows for sunbathing and stargazing, lounging and lawn games, grilling and campfires. With access to spectacular private association ocean beach, Hancock Beach, on the island's south shore in Chilmark, this rental offers a complete Vineyard experience.

Beautiful private spacious apartment

800+ square feet of light and bright apartment. My low priced cleaning fee keeps your total cost down. Enjoy the patio surrounded by trees. You may see our wild turkey visitor or local bunny. Our 2 dogs are friendly and will visit if allowed. That’s up to you! There’s a neighborhood behind the house with basketball courts and walkable residential area. The apartment is newly painted. Queen bed and couch that converts to a full bed. Smart tv and fast wifi. LGBTQ friendly.

Spacious 1850s rustic meets modern walkout studio

Located on 1.6 acres, just a 6 minute drive from Vineyard Haven town center, this lovely post and beam walk out basement apartment is the perfect home base to explore the island. Although the home was built in 2000 and has all the modern amenities you could hope for, its structure, reclaimed from a Connecticut dairy barn built in 1852 brings old world charm to this stunning space. Please note that our family of 5 lives upstairs so there is potential for noise.

Newly Renovated: Cul-De-Sac/Wifi/AC/BEACH-PASS

The spacious two-story 4-bedroom 2-bathroom family retreat located on Cul-De-Sac street with central AC, a private backyard with patio, porch, and outdoor shower, offers an open floor plan with two living rooms, ample seating throughout, and allows multi-generational families to socialize comfortably. The house sleeps 10 people with two kings, two twins upstairs, and 2 twin bunk beds downstairs.

Walk to Town/Golf Club - Renovated Edgartown Home

Location, location, location! The perfect Martha’s Vineyard retreat—walk to downtown Edgartown! Ideally located on a quiet street off Upper Main, just a 10-minute stroll to shops, restaurants, and near Edgartown Golf Club. Minutes to scenic bike paths and beaches. This fully renovated 2BR/2BA home features a new kitchen, bathrooms, furnishings, and comfortably sleeps 5.