We're searching thousands of homes to help you
find and book the perfect vacation rental.

Loading...

Chilmark Vacation Rentals in Massachusetts

1of 1 
  • Nicely situated "Up Island" in a scenic rural area of Middle Road. Very private & quiet.

    $150-$250 per night*
    • Chilmark
    • Vacation Home
    • Sleeps 5
    • 2 bedrooms,
    • 1 bath
    • No Pets
  • Description: Wonderful Bow roof cape nestled in the woods of Chilmark, minutes from Menemsha Basin, and the beach. Pine floors, fireplaces in living room and master bedroom. Soak up the sun on the…

    $300-$700 per night*
    • Chilmark
    • Vacation Home
    • Sleeps 7
    • 3 bedrooms,
    • 3 baths
    • Pets Allowed
  • Wooded property, with three private acres, within walking distance to the village of Menemsha and to the town beach, the Main house has two bedrooms and the guest house sleeps three.

    $700-$1,000 per night*
    • Chilmark
    • Vacation Home
    • Sleeps 7
    • 3 bedrooms,
    • 2 baths
    • Pets Allowed
1of 1 

*Final rates are based on travel dates and other factors.

Real-time Listings

ClearStay real-time listings give you all the information you need with up to the second accuracy to find, choose and book your rental.

  • Real-time availability information
  • Exact Rate Quotes
  • Ratings & Reviews
  • Bookable Online

Basic Listings

ClearStay basic listings provide property descriptions, photos and a link for you to contact the manager for rates, availability and booking.

  • Contact manager for availability
  • Contact manager for exact rate quote
  • Contact manager for bookings

More Vacation Rentals

The ClearStay Difference

The ClearStay Difference