Discover a selection of 393 vacation rentals in Chilmark, MA 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 $164 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.
Top rated rentals — Chilmark
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 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, MA?

Our 2020 property listings offer a large selection of 393 vacation rentals around Chilmark. From 372 house rentals to 23 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Chilmark?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Chilmark:

  • Katama: 262 vacation rentals
  • South Dartmouth: 189 vacation rentals
  • Falmouth Heights: 221 vacation rentals
  • Mews Village: 63 vacation rentals
  • West Chop: 16 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Chilmark?

Vrbo offers a large selection of vacation rentals near lovely places in Chilmark. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Menemsha Beach: 1,176 vacation rentals
  • Chilmark Chocolates: 1,142 vacation rentals
  • The Yard: 1,318 vacation rentals
  • Menemsha Blues Charters: 1,169 vacation rentals
  • Waskosim's Rock Reservation: 1,343 vacation rentals

But there are many other points of interest around Chilmark listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Chilmark?

Yes, of course. Vrbo has 372 Houses in Chilmark. Our other popular types of vacation rentals in Chilmark include:

  • Cottages: 23 rentals available
  • Cabins: 23 rentals available
  • Bungalows: 23 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Chilmark?

Yes, you can select your preferred vacation rental with pool among our 47 vacation rentals with pool available in Chilmark. Please use our search bar to access the selection of vacation rentals available.

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