103 Properties For Rent in Chilmark, Massachusetts

4 Bedroom house for rent in Chilmark, sleeps 8 starting $3500/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

3 Bedroom house for rent in Chilmark, sleeps 5

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

3+ Bedroom house for rent in Chilmark

3 Bedroom house for rent in Chilmark, sleeps 8

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...

4 Bedroom house for rent in Chilmark, sleeps 8 starting $12000/week

2 Bedroom house for rent in Chilmark, sleeps 3

4 Bedroom house for rent in Chilmark, sleeps 10 starting $12000/week

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

Walk to staircase down to amazing Private Atlantic Beach

Quintessential up-island cottage. Sleeps 2

4 Bedroom house for rent in Chilmark, sleeps 10

3 Bedroom house for rent in Chilmark, sleeps 8