Gay Head Classifieds > Housing > Vacation Rentals

Spacious four bedroom home situated high on Prospect Hill with magnificent views of the Elizabeth Islands and Aquinnah.

Come and enjoy this fabulous family retreat. Nestled in the trees off an historic lane in exclusive Chilmark. Relax on the deck with built-in seating overlooking an expansive view of south shore Atlantic Ocean. Awake to the chirping of birds and enjoy the fabulous up-island beaches. House is fully equipped with a new HDTV, DVR and wireless internet. The perfect up-island getaway.

Vineyard cottage with gorgeous views of Chilmark Pond and beyond. Located at Quitsa Pond Overlook. Owners have verbal agreement with dock owners to use the dock for short term use on, no tie-ups. Mooring & dingy available. Wheelchair access.

Front half of duplex unit.andnbsp; Back half may be occupied by other tenants.andnbsp; Private parking.andnbsp; Both front and back duplexes may be rented together - see BONE6.

Delightful 3 bedroom immaculately maintained.andnbsp;andnbsp;andnbsp; Private back yard and deck. Conveniently locatedandnbsp;near bike paths to beach and town.andnbsp; andnbsp;Additional features include Plasma TV, gas fireplace, WiFiandnbsp; and TV's in all bedrooms.andnbsp; *** OWNER OCCUPIES GUEST HOUSE TO THE LEFT.andnbsp; TENANT PRIVACY IS MAINTAINED ***

This charming Katama Cape house and guest cottage are located at the end of a private way in the desirable Katama area. Our Cape house features a bright open dining room with cathedral ceilings, skylights and hardwood floors. The kitchen has a center island with granite countertop and French doors leading out to a sunny deck. The first floor has a full bath and bedroom with a double bed. Second...

Luxurious Katama rental home home built in 2008. This upscale property offers high quality design, great flow for your summer vacation rental. Essentially two master bedrooms, on upstairs and on down, central air conditioning and minutes to South Beach. Enjoy beautiful sea breezy and sunsets across open fields with distant water views. The perfect home for the perfect Martha's Vineyard vacation.

Meetinghouse Way Condominium located in Edgartown, approximately 2 miles from the village. This two story centrally air conditioned Townhouse has the privacy of an end unit with a side and backyard equipped with a hammock in a quiet neighborhood setting. Tastefully decorated with a finished basement and a pool table. Be sure to end your day with a dip in the condo Association pool just steps away.

This Martha's Vineyard beach house has a wrap-around front deck with plenty of outdoor seating, screened in porch and a nice big backyard for a game of wiffle ball or grilling your favorite meal. This property is located on a quiet street only and only 1.5 miles to South Beach. Inside you will find an open floor plan of living, dining and kitchen with access to the decks via sliding glass doors.

Recently built guest cottage in Katama with central air, cathedral ceilings, quality textures throughout home, such as oak floors, tumble marble, limestone and corrian. A spacious master suite with full bath and whirlpool. Outdoor shower for those long days at the beach, a garage to house those who might have a convertible or motorcycle. Beach chairs, beach blankets and many more conveniences. ...

Private home set at the end of a cul du sac boarding the State Forest, within minutes to bike paths and walking trails. This newly furnished immaculate home features three bedrooms and has all the amenities one would want on vacation! The outdoor space features stone patio, gas grill, wrap around deck, above ground pool and gazebo with hot tub and outdoor shower. The backyard is fenced with a g...

Contemporary Vineyard farmhouse with farmers porch. Ideally located on a shady island road off the Edgartown-Vineyard Haven Road, close to bike path. Approximately 0.5 mile to shops, restaurants and 1.5 miles to downtown Edgartown or beaches. The house is situated on a quiet wooded area with little traffic and a large backyard with open deck and gas grill. Sunny, airy and open floor plan, creat...

Sprawling vintage Edgartown home just steps away from desirable Fuller Street beach. Separate two bedroom, two bath guesthouse with living area as well as an attached garage. Main house includes a private second floor master suite with access to a small rooftop deck - spectacular views of Chappy and Edgartown Harbor entrance. Fully equipped eat-in kitchen. Private beautifully landscaped yard. F...

A historic house in downtown Edgartown, built in 1836. Known as the Davis Academy, it was a school (and also community debating venue) in the 19th century. Bought by pulitzer prize winning journalist, James Reston, in 1969, it has recently been restored and renovated to pristine Vineyard standards.

Charming Frank Lloyd Wright Craftsman home located within several blocks to town and bike path. Spacious living room flowing into a country kitchen with ample seating for six as well as a laundry room. The house is furnished with antiques and top quality furniture and bedding throughout. Relax and enjoy the outdoor entertainment space which offers tiered decking, one for grilling and the other ...

Contemporary home with an open floor plan and lots of sunlight. Upper and lower level decks, great for relaxing and entertaining. Complete update to kitchen with new cabinets, granite countertops and new appliances and new tile flooring. Updated bathrooms include new vanities, mirrors and light fixtures. Convenient location, close to center of town and South beach.

Private home nestled in a country setting of Sweetened Water Farm, over 63 acres with just 12 homes in the association. Conveniently located, minutes away from both South beach (3 miles) and State Beach (2 miles), just off the bike path and 1/2 mile from downtown Edgartown. Quiet and off the beaten path, yet easy access to everything you need for a great vacation. The home is roomy and comforta...

Tastefully renovated in 2012, this saltbox has an open floor plan and hardwood floors throughout.andnbsp; Open dining/living area includes new furnishings and a wall mounted 55" HDTV.andnbsp; Kitchen has center island food prep/eating area (with 4 Stools) that opens to a deck and grilling area.andnbsp; The first floor has two bedrooms with bath.andnbsp; The second level features master bedroom,...

Immaculate cottage near the sea, nestled on a farm pond with pretty waterviews. Just a few steps to the end the street and you are at Ink Well Beach for a relaxing day on the water. Miles of scenic bike trails begin about a half a block from the house. Stroll the waterfrontandnbsp; to Oak Bluffs center where you will find fine dining or family friendly dining, movies, quaint shops, an arts dist...

East Chop three level modern home with waterviews from each level, the second level deck makes outdoor activities such as eating an enjoyable experiance.