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, HomeAway 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 412 vacation rentals around Chilmark. From 361 house rentals to 27 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a seaside property in Chilmark?

If you're wild about sea views and the sound of waves, you're in luck! Luckily, there are 121 beachside vacation properties to spirit yourself away to. Alternatively, you might prefer trying something else. Vrbo has no lack of options to choose from, including:

  • 66 rural vacation rentals.
  • 62 water-view vacation rentals.
  • 53 village vacation rentals.

Can I rent a house in Chilmark?

If you're seeking a home away from home for your trip, renting a house is a terrific idea. You'll have the space you need for all your vacation activities. There are 307 options currently listed on Vrbo. Prices start at $225 a night. If that doesn't match your squad's style, we've got a number of other rental options available, such as:

  • Cottage: 24 vacation homes. Prices start from $200 per night.
  • Condo: 8 vacation homes. Prices start from $295 per night.
  • Townhome: 5 vacation homes. Prices start from $260 per night.

Can I stay in Chilmark in a large group?

There's nothing quite as exciting as being somewhere entirely new with close friends and family. And the great news is Vrbo has some options to suit large groups. The top choice for larger groups here are house vacation homes, and we have 108 available. Rental properties in this area that can cater for large groups include:

  • On the lookout for vacation homes that can hold 8 vacationers? We have 113 that will suit. Prices begin from just $271 per night.
  • If you have 6 in your party, you'll be happy to hear that there are 64 vacation homes suitable. Prices start at $225 per night.
  • Seeking places for rent catering to 10 guests? You'll be delighted to know we have 64 that will fit the bill. You can get one for as little as $311 per night.

So don't fear! When you book with us you can bring your dad, your grandma and all your pals to Chilmark.

Where are the cheapest rentals in Chilmark?

Say au revoir to sterile, drab hotel chains! Delight in the ease of staying like a local in a cost-effective rental instead. Have a look at the amazing options that can be snapped up now on Vrbo. When it comes to seeking out a fantastic deal, your first port of call ought to be Woods Hole. Here, Vrbo has 54 rentals at an average price of $315 a night. Buzzards Bay is another great option. We've got 102 rentals here, and the average price is around $330 per night.