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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!

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.

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

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.

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

Secret Garden Suite with full breakfast

We built our home in 1997 and have shared it with our five children, grandchildren and extended family. We thought someday when the kids leave, we will make it into a Bed & Breakfast and Airbnb has made the dream simply possible. Joining Airbnb in May 2016 changed and enriched our lives by the many travelers we have hosted and friends we have made. We look forward to being your host soon. We believe that the breakfast we include with the room rate adds substantial value.

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

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.

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.

Glendale Petite @ Frederick William House

The Glendale Petite Room is Double Deluxe Room at Frederick William House. Located on the Shining Sea Bikeway in Falmouth Massachusetts across the street from Goodwill Park. Your stay includes bike rentals. Short walk to the Steamship Authority parking & shuttle to the ferry boat. Guest are welcome to take bikes over to Martha's Vineyard for day excursions. Beach passes are available allowing access all 139 private & public beaches.

Relaxing Retreat in Falmouth

Escape to this cozy 2BR Cape Cod retreat in the gated Sun Retreats Resort! Enjoy pools, hot tub, private beach access, fishing, paddleboards, mini golf, and family activities—all just minutes from downtown Falmouth. Relax on your private deck with a fire pit after a day in the sun. Pet-friendly, Wi-Fi included, and perfect for families or couples. The ultimate affordable Cape getaway awaits—book your stay now!