Vacation rentals with breakfast in Dukes County

Vineyard Haven Family Beach, Fire Pit & Garden Vie

Escape to Vineyard Haven House, a stunning holiday home perfect for your next getaway! This beautiful house boasts 4 spacious bedrooms, 2.5 bathrooms, and multiple living areas with cozy fireplaces. Enjoy direct access to the lake, a private dock, and fantastic outdoor amenities, including a fire pit, gas grill, and outdoor shower. Located in a tranquil neighborhood, you're just a short drive from beaches, shops, and the ferry to the islands. Relax and unwind in this idyllic retreat, offering th

Family · Location · Kitchen

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!

Value · Family · Comfort

Pilot House- The Famous Menemsha Inn Cottage

Pilot House is the Menemsha Inn Cottage made famous as the base camp for 50 summers for legendary life photographer Alfred Eisenstaedt. Full kitchen, living room with wood burning fireplace and Roku TV. It includes a private deck with chairs and a screened-in porch with a picnic table. Additional amenities include outside showers, BBQ grill, use of the inn's facilities, and walk-on or car passes to a choice of Chilmark's Private Beaches - Lucy Vincent or Squibnocket during beach pass season.

Location · Value · Heating

Vineyard Haven Harbor 60’ sailboat 2 Cabins 4 beds

Gently rock yourself to sleep on a big beautiful classic sailing yacht. This listing is two Cabins on Tandemeer, a 1980 sailing ketch, 60' long and 15 feet wide. These are the two forward staterooms. Each stateroom has two large comfortable single beds, with storage space underneath for luggage, fans, an opening ceiling hatch, and a private toilet, sink and shower. The spacious main salon, cockpit and deck areas are also available for lounging and enjoying the view from your yacht on the water

Family · Location · View

Top guest favorite

Guest favorite

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.

Family · Value · Decor

Top guest favorite

Guest favorite

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.

Location · Value · Wifi

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

Location · Value · Air conditioning

The Look Inn/Parrish Room

The Look Inn is a licensed bed and breakfast Inn by the Town of Tisbury/Vineyard Haven celebrating our 35th year of operation. The Parrish and Blue and Look Out Rooms have a queen size bed and can sleep one or two people. The rooms shares a full bath with the rooms that each have sinks with hot/cold water and the common spaces of living room with tv and screened porch. There are relaxing lawn chairs that view the many gardens of flowers and vegetables. Serving guests over 18

Value · Location · Sleep quality

Top guest favorite

Guest favorite

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.

Value · Family · Amenities

Top guest favorite

Guest favorite

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.

Value · Location · Layout

Charming King Room - Woods Hole Inn

This beautiful vintage meets modern style inn is a 10-minute walk from the beach and right across from the ferry to Martha's Vineyard in Woods Hole. Free private parking and free WiFi is available on site. Easy walk to the beach, several restaurants, and most science facilities. Guests can enjoy various activities in the area, including windsurfing, fishing, and traveling to Martha's Vineyard.

Location · Value · Walkability

Top guest favorite

Guest favorite

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.

Location · Family · Indoor spaces