Holiday rentals with breakfast in Dukes County

Oak Bluffs/ Harbor Views/ Full 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.

Ocean Park Victorian

Private suite in Ocean Park Victorian home. Private locking entrance to second floor sunny bedroom, breakfast/sitting room, private bath with tub, shared outdoor shower. English muffins, OJ, and jam are provided and there is a Keurig coffee-maker for your use. At your leisure enjoy your muffin and coffee in the sitting room or outside on the deck or front porch. Enjoy the beautiful town beach at the end of the street. Easy walking distance to the ferries, beach,restaurants, and shopping.

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 ($75). To book two separate beds you must specify 3 people in your party.

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

Bright, Unique on Martha's Vineyard!

SPRING SPECIAL through June 15: Min Stay 2 nights, stay third night, get 30% rebate from hostess! A spacious room with bath in a studio behind my house, opens onto a broad meadow, abuts bike & walking trails. Serene, yet just 5-20 minutes from beaches & towns & all the lively Island happenings. If you are coming for a wedding, an anniversary, a reunion or just for the humming of nature and the sea, The Broad Meadow is for you. NO ROOM TAX - Good breakfast & beach passes!

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.

Vineyard Charm Island Memories

This is a Vineyard home, not a house on the Vineyard! Charming and eclectic, the house was built in 1868 and is an original Gothic Victorian Methodist Campground. The home has been recently renovated yet retains its vintage roots. The Airbnb bedroom is downstairs with private bathroom and a separate entrance. Pets allowed—one-time dog fee of $35, choose *extra guest* option to add this cost. Keep in mind we have 2 full size English Mastiffs that live here full time.

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.