Discover a selection of 397 vacation rentals in Chilmark that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $175 per night, and houses and cottages are popular options for a stay in Chilmark. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Chilmark
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Destination guide

Head to the tranquil city of Chilmark

The area's wineries and festivals are just a few of the reasons to vacation in Chilmark. This city's beaches, hiking and local tours attract many visitors, and its relaxing and scenic location add to the charm. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities

Activities and attractions in and around Chilmark

Do you want to discover top things to see and do while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Chilmark a fun place to get away. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Island Cove Adventures (9.7 mi / 15.7 km)
  • Farm Neck Golf Club (11.2 mi / 18 km)
Natural features

Exploring the natural features in Chilmark

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Chilmark. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • Menemsha Beach (0.9 mi / 1.4 km)
  • Lucy Vincent Beach (1.4 mi / 2.3 km)
  • Aquinnah Cliffs (4.5 mi / 7.2 km)
  • Polly Hill Arboretum (5.1 mi / 8.2 km)
  • Long Point Beach (6.1 mi / 9.8 km)
  • Cedar Tree Neck Sanctuary (6.3 mi / 10.2 km)
How to get there

Transportation to and around Chilmark

Fly into Vineyard Haven, MA (MVY-Martha's Vineyard), the closest airport, located 7.7 mi (12.5 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to New Bedford, MA (EWB-New Bedford Regional), which is 24.8 mi (39.9 km) away.

How many vacation rentals are available around Chilmark?

Our 2021 property listings offer a large selection of 397 vacation rentals around Chilmark. From 374 house rentals to 22 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.