Oak Bluffs Classifieds > Housing > Vacation Rentals

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 ...

Beautiful Custom built, 4 bedroom, 2.5 home in Seaside New Seabury neighboorhood of Little Neck Bay, close to South Cape Beach. Open, light and colorful, immaculate home with new furnishings that features, 1st floor master suite with private bath, spa tub, wood floors, central A/C, Plasma TV s, screen porch sitting area, 2 decks and patio. Three 2nd floor bedrooms, all with queen beds and also ...

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!

An absolutely charming, traditional Chappaquiddick cottage furnished with cottage antiques. Gorgeous views of the Edgartown outer harbor from the front porch . 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!

Chappaquiddick cottage furnished with cottage antiques. Gorgeous views of the Edgartown outer harbor from the front porch . Private beach just steps away. NOTE: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!

Exceptional new home on Chappaquiddick. Recently built, this three bedroom home has incredible waterviews from just about every room. Walk to private beach or a short distance to Wasque. NOTE:Please go to the "ISLAND INFO" link on our website and click on "Chappaquiddick" for additional IMPORTANT information on living on this magic little island!

This informal Chappy Cottage is located in a wooded area about midway between the Cape Pogue Wildlife Refuge and the Wasgue Reservation, both of which have glorious hiking trails and beaches (there is a small entry fee). It has easy access to the road that leads to the Chappy ferry. NOTE:Please go to the "ISLAND INFO" link on our website and click on "Chappaquiddick" for additional IMPORTANT in...

This is a lovely home on Chappaquiddick that was developed over the years to accommodate multiple generations and be the center of family vacation fun while maintaining its original charm. Like many of the original Chappaquiddick houses the focus is on the family areas. It has a spectacular view of the outer harbor, East Chop and the Cape (on a clear day). The Main House has 2 living rooms (one...

Situated along Edgartown's inner harbor, this quintessential Vineyard home invites you to relax and watch the glorious sunsets. This well equipped home offers many amenities of modern living including high speed internet. Two kayaks are available for exploring the harbor or Caleb's Pond. Come to this harbor side Chappy gem with your own private beach and your own private dock. Also Caleb's Pond...

This home has been kept in excellent condition, yet still retains a New England colonial/island feel. The house sits on 12 secluded acres with breathtaking views of Katama Bay and the southern shore. It is a waterfront home with 570 feet of private beach on Katama Bay. The distance to the beach is less than 200 yards. NOTE:Please go to the "ISLAND INFO" link on our website and click on "Chappaq...

Beautiful and perfectly located home on top of Chappy's Sampson Hill with heated pool, gardens and jacuzzi, large yard and porches. All beaches and amenities just 1 mile away. Never see traffic or parking jams, your exclusive home is 1 mile to beach. The home centers on old native walking/biking paths connecting to all beaches on Island. PLAY ON CHAPPY's famous beaches during day AND AT NIGHT, ...

Situated with two other houses on a wonderful, 88 acre, waterfront estate of rolling hills and woods with hiking trails, this secluded "Artist's Barn" has a 2 story living room with oak beams, fieldstone fireplace and sliding glass doors overlooking the low deck. A long sweeping meadow leads down to a private beach (rocky) with a little Beach Camp (shared with Main House permission). Loft has q...

Charming Chappaquiddick cottage with distant views of Katama Bay. Relax on the deck after a day at the beach - Katama Bay is only 300 yards away!