Gay Head Classifieds > Housing > Vacation Rentals

Nestled in a wooded, private setting located off of Moshup Trail in Aquinnah. Great up-island retreat, just two miles to private Philbin Beach. Bright, cheerful and spacious interior, open and clean living space. Enjoy and relax on the outdoor deck perfect for sunning, reading and/or grilling. The perfect up-island get away.

In a private setting, this lovely, classic, vineyard home, with herb & perennial gardens, is set at the edge of a lawn that slopes down to the water & beach on Katama bay. It is beautifully decorated w/antiques and fine quality furnishings that complement the relaxed, semi-formal style of the home. All rooms look west to the harbor and Katama bay over a salt marsh and pond with an active osprey...

Located away from the crowds (but only a ten minute drive to the ferry & Edgartown town), this casual, cozy & charming home, with a Guest House attached via a large deck, is in a natural setting is a great spot to escape to. With both bay and ocean beaches close by, you can walk or drive to water....or relax at the house on the sunny rear deck, or in the shade on the covered front porch. There'...

Close your eyes and envision a summer in the romantic yesteryears when Chappaquiddick was a remote outpost, yet here was an amazing rural estate, Carriage House and all. Back then one had to be rowed across to this little island from Edgartown, there was no electricity and hand pumps for water & outhouses were the norm. As evidenced by the photographs, much has changed and modern luxury surroun...

It is located atop Sampson’s Hill being the highest elevation in Edgartown. Between now and the start of this upcoming summer, we will have updated and renovated the home completely. The house is an upside down house consisting of three levels with the top level being the shared living quarters consisting of the living room, dining area, and kitchen giving way to a spectacular panoramic v...

NEW LISTING - awaits verification by owner: Charming Chappy Cottage with gorgeous water views and only a short walk to one of several beautiful beaches. The cottage sleeps four comfortably with easy living and well appointed kitchen. Front and back decks available for enjoying memorable sunsets. Non smokers only and no pets permitted. Perfect for small groups or families. Enjoy the airy floor p...

Comfortable, open design, home with view of fields and historic farm house, this newer home borders conservation property & walking trails, and is one mile from the ocean beaches. Secluded setting with three bedrooms upstairs, sleeps 6-8; 2 half baths and one full bath; outdoor shower, large screened porch. Bonus room in basement with ping pong table and TV. An added plus is the Association bea...

Ideally located on Stonewall Beach and Pond, panoramic water views. Open floor plan with lots of light, nicely furnished with gourmet kitchen and outdoor deck, perfect for entertaining. A great vacation home to unwind and enjoy the beauty of the Vineyard.

The Guest House (see #1289 for Main House)is approximately 1400SF and includes a Master Bed and Bath with a stand up glass enclosed shower. There is an additional bedroom and bathroom with a tub. A special feature is the state of the art kitchen as well as a great family room. There is an outside shower and nice deck off the front of the house. There will most likely be a chiminea or fire pit o...

One of those wonderful "Chappy" summer homes, this one is a reverse design with glorious waterviews over the end of Katama Bay to the ocean beyond. As it faces West the sunsets can be breathtaking! It is on a short,dead end dirt road with only a scattering of other houses in the area. Its proximity to Wasque, a favorite ocean beach and fishing spot, makes it a popular location.

Located just off Wasque Road this comfortable, well maintained home lends itself to a relaxed, informal vacation experience. It is just minutes from all of Chappaquiddick's wonderful beaches! The flat yard lends itself to those wonderful summer pastimes like badminton, whiffle ball, or whatever else on might dream up. Come and enjoy! NOTE:Please go to the "ISLAND INFO" link on our website and c...

The beautiful,sandy, private association beach is the perfect compliment to this well maintained & appointed vintage Vineyard cottage. This adorable home was one of the first to be built along the bluff overlooking the inner harbor on Chappy. Set on two acres, this cottage boasts a panoramic view of Edgartown and Katama Bay. Extraordinarily private location with short walk to town and private, ...

NEW LISTING - PICTURES & FULL DESCRIPTION FORTHCOMING! 360 Degree water views from this newly built upscale Chappy home. Situated on top of Manaca Hill overlooking the inner and outer Edgartown Harbors, this three bedroom home is spacious and tastefully decorated. Outdoor living space includes stone fireplace perfect for evening cocktails while enjoying the boats sailing by. Over sized gourmet ...

This sweet Vineyard Haven home blends historic character with fresh and tasteful upgrades throughout. With a focus on comfort and amenities, this charming home is a delightful place to call home. Check-In: Sunday 3 p.m. Check-Out: Sunday 10 a.m.

This beautiful new home affords breathtaking views of the Vineyard Sound. You'll enjoy the best of the south end of the Island, including access to Philbin and the colorful Cliffs beaches. There's also Lobsterville and West Basin for calmer waters and hungry fishermen! Built and completed in 2001, this home will suit the most discerning tenants, and you'll have fun too! Gourmet dining right at ...

Beautifully maintained five bedroom traditional style post and beam house, located in a very private area with waterviews over Lobsterville Beach and the Elizabeth Islands.

The surrounding area is a throwback to a different time as there really isn’t much going on except beautiful beaches, extraordinary sunsets, the sound of the waves crashing in the distance as you sit on the deck with the clearest night skies you’ve ever seen. Spacious & well decorated, this home is located on 4 acres. There are 5 bedrooms & 3.5 bathrooms in this 4,300 square foot ho...

Sitting on the beach with the water of Vineyard Sound a stone's throw away, this west-facing, casual "beach" house has glorious views of boats, birds & golden sunsets. The double decks allow for casual get togethers, outdoor dining, and afternoon naps in the sun. A glass of iced tea, a good book and good company is all it takes to make this home a great vacation haven.

This rambling summer cottage is located in a private setting down a country road and is wonderful spot to spend those lazy, hazy days of summer. It is casual in feel, but it is well equipped and comfortable. The walk to the beach is about 10 mins down the sandy driveway. There is also a straight Sherriffs Meadow path down to the bluff to view the bay. There is an area for 2 cars to park down at...

Beautiful 3-Bedroom traditional Chappy cottage with specatular views of Edgartown light house and the outer harbor from the screened in porch. Meticulously maintained. Private beach just steps away. Please go to the "ISLAND INFO" link on our website and click on "Chappaquiddick" for additional IMPORTANT information on living on this little magic island!