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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!

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

The Mary Suite- Kathleens Kottage- Oak Bluffs MV

Kathleen Nasser is the owner of Kathleen's Kottage, a seasonal Host Home located in Oak Bluffs, MA. This is the Mary Suite the most private and spacious room. The suite is located on the second floor of the building adjacent to the main house. The suite has a private entrance with a lockable door. King size bed. Private bath with dual sinks. Sitting room. Cable TV, AC and Internet. Microwave, Refrigerator and Coffeemaker. Serving a light fare breakfast. We are small Pet Friendly.*

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.

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.

Park Side Queen Room @ Frederick William House

This beautifully appointed room with private bath & sitting area, includes bike rentals, cable, free WIFI, overlooking gardens & park. We are located on the Shining Sea Bikeway in Falmouth, across the street from Goodwill Park, a short walk to the Steamship Authority. Guest are welcome to take bikes over to Martha's Vineyard for day excursions. Beach passes are available, 139 private & public beaches to choose from.

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!

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.