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Chilmark vacation rentals

We found 527 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Select from 67 homes, 12 cottages, and other vacation rentals in Chilmark to find one that's perfect for your trip. Vacation homes provide the best amenities for you and your friends, family, or even pets, like air conditioning and cable TV. At the end of the day, you'll find a rental for everyone's needs, including accessible or non-smoking choices.

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Explore the beachside setting in Chilmark

The area's wineries and festivals are just a few of the reasons to vacation in Chilmark. Well-liked for its beaches, hiking and local tours, this city is both relaxing and scenic. 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

Are you searching for attractions to see 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 one-of-a-kind vacation spot. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Shining Sea Bikeway (17.2 mi / 27.7 km)
  • Farm Neck Golf Club (11.2 mi / 18 km)
  • Chilmark Chocolates (0.1 mi / 0.2 km)
  • Menemsha Blues Charters (1.3 mi / 2 km)
  • Fulling Mill Brook Preserve (2.5 mi / 4 km)
  • Island Cove Miniature Golf (9.8 mi / 15.8 km)

Exploring the natural landscape of Chilmark

Whether you're looking for adventure or just want to take in the scenery, Chilmark is a great spot to appreciate mother nature. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Menemsha Beach (1.4 mi / 2.3 km)
  • Aquinnah Cliffs (4.8 mi / 7.8 km)
  • Lambert's Cove Beach (8 mi / 12.9 km)
  • Katama Beach (8.6 mi / 13.9 km)
  • South Beach (11.4 mi / 18.3 km)
  • Inkwell Beach (12.5 mi / 20.1 km)

Transportation options to and around Chilmark

The nearest airport is in Vineyard Haven, MA (MVY-Martha's Vineyard), located 7.6 mi (12.2 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to New Bedford, MA (EWB-New Bedford Regional), which is 25.4 mi (40.8 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Chilmark?

Houses are the most popular type of vacation rental in Chilmark, according to our data. Even if you have a different idea about what you want, Vrbo has properties in many sizes and shapes. Browse our options to find your ideal fit.

How much does it cost to rent a vacation rental in Chilmark?

Property type, length of stay and season are some factors that can affect the price of a vacation home. Simply add your dates of travel to find your perfect fit. From quaint country cottages to plush villas, all Vrbo vacation rentals offer incredible value.

How much does it cost to rent a beach house in Chilmark?

Prices for beach houses in Chilmark differ depending on the size and type of the property and when you're traveling. Simply enter your dates of travel into Vrbo and the number of guests to view your rental options and prices. From there you can use the filters to tailor your search by amenities, nearby activities, ratings and more.

Are there pet-friendly vacation rentals in Chilmark?

Yes. There are. You'll have your pick of 63 vacation rentals that cater to pets in Chilmark. Several of our pet-friendly vacation rentals have a garden for your fur baby to play in, doggie beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find your pawfect pad on Vrbo.

Can I rent a house with a pool in Chilmark?

Check the "pool" box in our handy filter tool and you'll find eight houses with private pools in Chilmark on Vrbo. Morning dip, sunset soak or midnight swim? Leisure time is up to you when your vacation home comes with its own pool.

What are popular rental amenities in Chilmark?

When it comes to rental amenities that people are on the lookout for in Chilmark, a chef, a water view and tennis rank the highest. With Vrbo vacation homes, you'll have options to suit your taste and style, whether you're taking a trip with your partner, your friends or even pets.

Are there large group vacation rentals in Chilmark?

With 14 properties that can host 10 guests or more in Chilmark, you don't have to limit the invite list. From fun family get-togethers to special events like birthday parties and weddings, Vrbo will help you find a large group rental that fits the occasion.

Are there vacation rentals in Chilmark that welcome kids?

Bring the whole group together for the adventure of a lifetime in Chilmark at one of our 61 family-friendly vacation rentals. A lot of these stays feature amenities that are suitable for getaways with the little ones, such as laundry facilities, living rooms and swimming pools. Simply check the "Properties good for families" filter and choose your favorite.

What are the top attractions for families in Chilmark?

Keeping the kids entertained during your vacation in Chilmark is simple with these leading family-friendly attractions:

  • Lamberts Cove Beach
  • Menemsha Beach
  • Lucy Vincent Beach

Are there one-bedroom vacation rentals in Chilmark?

Chilmark has two one-bedroom rentals on offer. Usually situated in sought-after areas thanks to their smaller size, a one-bedroom vacation rental is great if you're traveling with a pal or your partner. And with home comforts like kitchens and more privacy than a standard hotel, you'll be able to kick back while sightseeing around this fabulous destination.

Can I find two-bedroom vacation rentals in Chilmark?

You can pick from 10 two-bedroom homes in Chilmark. Settle the kids into the second room or fill it with a couple of your besties. There's enough space for whoever's fortunate enough to be coming along for the ride.

Are there vacation rentals with WiFi in Chilmark?

Choose from 26 vacation rentals with WiFi in Chilmark. If you want to disconnect from daily life on your vacation, but still want to be connected to the internet, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.

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