Photo by Wen C.

Chilmark holiday rentals

We found 517 holiday rentals — enter your dates for availability

Select from 69 homes, 10 cottages and other holiday rentals in Chilmark to find one that's perfect for your trip. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as cable TV and a washer and dryer. At the end of the day, you're sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Explore the beachside setting in Chilmark

The area's wineries and festivals are just some of the reasons to come on holiday to Chilmark. Revered for its beaches, hiking and local tours, this city is both relaxing and scenic. If you're looking for accommodation options 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 find things to do in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Chilmark a fun place to get away to. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Shining Sea Bikeway (17.2 mi / 27.7 km)
  • Farm Neck Golf Club (11.2 mi / 18 km)
  • Oak Bluffs Fishing Pier (12.6 mi / 20.3 km)
  • Cape Cod Winery (18.4 mi / 29.6 km)
  • Chilmark Chocolates (0.1 mi / 0.2 km)
  • Fulling Mill Brook Preserve (2.5 mi / 4 km)

Exploring the natural landscape of Chilmark

Whether you're an adventurous traveller or just want to take in the scenery, Chilmark is a great place to get outside. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Edgartown Beach (11.4 mi / 18.3 km)
  • South Beach (11.4 mi / 18.3 km)

Transport 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 centre. 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 holiday home accommodation in Chilmark?
Houses are the most popular type of holiday home in Chilmark, according to our data. Even if you have a different idea about what you want, Stayz has properties in many sizes and shapes. Browse our options to find your ideal fit.
How much does it cost to rent a holiday home in Chilmark?
Property type, length of stay and season are some factors that can affect the price of a holiday home. Simply add your dates of travel to find your perfect fit. From quaint country cottages to plush villas, all Stayz holiday homes 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 travelling. Simply enter your dates of travel into Stayz and the number of guests to view your home 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 holiday homes in Chilmark?
Yes. There are. You’ll have your pick of 63 holiday homes that cater to pets in Chilmark. Several of our pet-friendly holiday homes 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 Stayz.
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 Stayz. Morning dip, sunset soak or midnight swim? Leisure time is up to you when your holiday home comes with its own pool.
What are popular home amenities in Chilmark?
When it comes to home amenities that people are on the lookout for in Chilmark, a chef, a water view and tennis rank the highest. With Stayz holiday 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 holiday homes 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, Stayz will help you find a large group home that fits the occasion.
Are there holiday homes 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 holiday homes. 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 favourite.
What are the top attractions for families in Chilmark?
Keeping the kids entertained during your holiday in Chilmark is simple with these leading family-friendly attractions:

  • Lamberts Cove Beach
  • Menemsha Beach
  • Lucy Vincent Beach

Are there one-bedroom holiday homes in Chilmark?
Chilmark has two one-bedroom homes on offer. Usually situated in sought-after areas thanks to their smaller size, a one-bedroom holiday home is great if you’re travelling 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 holiday homes 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 holiday homes with WiFi in Chilmark?
Choose from 26 holiday homes with WiFi in Chilmark. If you want to disconnect from daily life on your holiday, 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 Stayz.
How can I find holiday homes with air conditioning in Chilmark?
Pick your travel dates and then use the filter tool to find holiday homes with air conditioning in Chilmark on Stayz. With 45 air-conditioned properties on offer here, you can enjoy a cool and comfortable trip.
How old do you have to be to rent a holiday home in Chilmark?
The minimum age allowed can vary across properties on Stayz, so check the rules of the holiday home in Chilmark you’re interested in. But in general, it’s 16, 18 or 21.
How long can I rent a holiday home in Chilmark for?
The amount of time you can rent a Chilmark holiday home for differs depending on the property. Just enter your travel dates to view options that offer extended stays. They come with all the things you need to make your extended holiday more comfortable such as laundries and air conditioning. Some holiday homes may also offer discounted weekly or monthly prices, so you can stick around for longer for less.

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