99 Properties For Rent in Chilmark, Massachusetts

Stunning Waterviews of the Vineyard Sound from this Hilltop Contemporary

Vintage modern Chilmark House set in a meadow just a short drive to Lucy Vincent and Chilmark Center

Chilmark cottage with prime location between Chilmark Store and Menemsha Village

Waterfront house on Lucy Vincent Beach. Kayak or walk to the beach from this newly renovated beach house.

Set on a ridge in Chilmark off Middle Rd.

Rambling shingle style farmhouse updated to todays standards & lifestyles.

New rental with in walking distance to the beach.

Beautiful new guest house in Abel's Hill neighborhood. Access to Association south shore beach and tennis courts.

Lovingly restored this newly refurbished home is the perfect beach getaway.

Beautiful 3 bedroom home and summer cabin on 5 private acres

4 Bedroom house for rent in Chilmark, sleeps starting $7000/week

3 Bedroom house for rent in Chilmark, sleeps 7

Surrounded by meadows and stonewalls, this authentic antique is charming and functional

One mile to Lucy Vincent Beach from this waterview home on historic Ocean View Farm Road.

Bedroom house for rent in Chilmark, sleeps 6

5 Bedroom house for rent in Chilmark, sleeps 10 starting $16500/week

Fabulous double view from this newly renovated spacious home high on a hill overlooking the Atlantic! $25000/week

2 Bedroom house for rent in Chilmark, sleeps 4+

4 Bedroom house for rent in Chilmark, sleeps 8

5 Bedroom house for rent in Chilmark, sleeps 10

Menemsha four bedroom waterview home. Restyled, refurbished.

5 Bedroom house for rent in Chilmark, sleeps 10 starting $6000/week

Wonderful clean space with new kitchen modern feel with great aesthetic design

Spectacular Amenities abound in this much sought after area. Two ocean beaches, Squibnocket Pond Access and walking trails

Perfect for a large family looking for a relaxed vacation home with wonderful amentities. Key to South shore Atlantic Beach, Tennis and beachy...