Holiday rentals with breakfast in Dukes County

Find and book unique Holiday Accommodation with Breakfast on Airbnb

Top-rated Holiday Accommodation with Breakfast in Dukes County

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Place to stay in Oak Bluffs

4.55 out of 5 average rating, 29 reviews

Classic MVY Cottage, private, prime location, 2BR

"It's an amazingly quaint spot" With a bit of reconstruction, we have transformed a cozy 1933 fishing cabin into a charming cottage wrapped by world-class gardens. This property is perfectly suited for a single traveler, couple or small party of 3 (maximum), seeking privacy & solitude. We are a mere bike ride to Eastville Beach, the Harbor and Circuit Avenue. Enjoy backyard cookouts, shopping, sailing, fresh seafood, chocolates & more. Let this Cozy Cottage become part of your MVY memories.

Home in Oak Bluffs

4.91 out of 5 average rating, 11 reviews

Colorful + Stylish Cottage in Oak Bluffs

Welcome to the 1871 Gingerbread Cottage of our dreams! We have renovated this house by hand and spend much of our time here filling it with love and memories. When our own family isn't here, we open it to you + yours! The cottage was featured in the May/June '16 issue of Yankee Magazine, as well as several design books. We are within walking distance of the Oak Bluffs ferry terminal, Circuit Avenue's restaurants and bars, and several beaches. Lighthouses + more are just a short bike ride away!

Superhost

Private room in Oak Bluffs

4.92 out of 5 average rating, 61 reviews

Oak Bluffs/ In Town/ Harbor Views/ Full Bed

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!

Superhost

Guest suite in Edgartown

4.91 out of 5 average rating, 96 reviews

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.

Home in Falmouth

4.91 out of 5 average rating, 23 reviews

Enjoy Falmouth Heights Beach ANYTIME!

Beautiful home down the street from the Heights beach! The house flows openly to the wrap around porch that is perfect for grilling, gatherings and sunset cocktails. There is a washer and dryer in basement and ample off street parking. The house has central a/c that each room can control. If preferred, enjoy the beach air with the windows open! Located close to beaches, restaurants and attractions: bike bath, Woods Hole, Island Queen boat to MV, Falmouth Road Race finish line and so much more.

Top Guest favourite

Private room in Oak Bluffs

4.99 out of 5 average rating, 190 reviews

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.

Guest favourite

Home in Edgartown

5 out of 5 average rating, 55 reviews

Walk to Town/Golf Club - Renovated Edgartown Home

The perfect retreat for your escape to Martha's Vineyard, walking distance to downtown Edgartown! Location, location, location! We're a stone's throw from Edgartown Golf Club and all the amazing restaurants + shops are just a 10 minute stroll. This 2-bedroom, 2-bathroom home has been completely renovated, with an all-new kitchen, bathrooms, furnishings, linens & accessories. The house accommodates 5 people very comfortably, and is located on a quiet residential street just off Upper Main.

Guest favourite

Private room in Edgartown

4.83 out of 5 average rating, 504 reviews

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.

Cottage in Oak Bluffs

4.89 out of 5 average rating, 116 reviews

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

Guest favourite

Guesthouse in Vineyard Haven

4.94 out of 5 average rating, 126 reviews

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.

Top Guest favourite

Private room in Oak Bluffs

4.99 out of 5 average rating, 281 reviews

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.