Discover a selection of 470 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 air conditioning. Prices start at $197 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

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.

Things to do

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

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:

  • 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 (11.1 mi / 17.8 km)
  • Inkwell Beach (12.5 mi / 20 km)
  • Oak Bluffs Town Beach (12.6 mi / 20.3 km)
How to get there

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 Hyannis, MA (HYA-Barnstable Municipal), which is 32.6 mi (52.5 km) away.

What are the top vacation rentals in or near Chilmark?

Whether you're looking for a cozy escape for you and your love or somewhere roomy to fit all your friends, you'll find some top vacation rentals in and around Chilmark. Here are a couple to get you inspired:

  • Around 18 miles from the center of Chilmark, it's hard to top "Panoramic Views Of Snug Harbor In Beautiful West Falmouth". It has 6 bedrooms and a range of amenities including an electric kettle and a free nearby fitness center.
  • Alternatively, make yourself comfortable at "Exceptional - Waterfront Home". Around 20 miles from the heart of Chilmark, it has 3 bedrooms and features cable/satellite TV services and WiFi.

For even more great options, use the search bar at the top of the page to find the perfect Chilmark vacation rental for you.

What are the best tiny house vacation rentals in or near Chilmark?

You need only take a peek inside our tiny house vacation rentals in Chilmark to figure out that awesome things really do come in small packages. Sensibly designed to maximize space, these pocket-sized digs deliver a big vacation experience:

  • Leave the world behind and disappear to "Marion Village's Very Best Cottage - Tiny Home Living Close To The Town Beach". This getaway in Marion Center packs plenty of comforts into its cozy space, such as spa and beauty services and an oven.
  • Alternatively, book a couple of nights at "Stay In A Tiny House 0. 4mi To Beach Village Restaurants Pet Friendly 2 Bikes". Located in Dennis Port, this teensy abode comes with outdoor furniture and internet services.

Can I find log cabins to rent in or near Chilmark?

You certainly can! From rustic hideaways to upmarket escapes, Vrbo has a range of log cabins to rent in or around Chilmark. If you're the adventurous type, here's where you can go:

  • "Spacious Wellfleet Tree Top Log Cabin Great For Families And Reunions": Enjoy a week unwinding and relaxing at this superb escape nestled in nature. Once you've reenergized, enjoy fishing or kayaking, which are some of the leading activities in this area.
  • "Rustic Cozy Log Cabin": After a big day of trying out some popular local pastimes, such as snowboarding and kayaking, wind down at this cozy property.

What are the top-rated vacation rentals for weekend getaways in or near Chilmark?

Nothing's better than squeezing in a quick break to revive your spirits. Pack your overnight bag and get cozy in one of these appealing weekend getaways in and near Chilmark:

  • "Luxurious Estate Includes - Tennis Court" is a comfortable option around 30 miles northeast of central Chilmark. You'll never need to venture far to find something to keep you busy around this escape. Get out and explore Springhill Beach and National Marine Life Center. Activities like basketball and ice skating will add the finishing touch to your mini break.
  • Alternatively, make your home away from home at "Located Steps Away To Main Street And. 7 Miles From Surf Drive Beach". Stay in and put your feet up, or head out and try your hand at some windsurfing and basketball. When it's time to discover more of the area, organize a visit to Fallriver Heritage State Park and Children's Museum of Greater Fall River. This attractive vacation rental is around 16 miles northeast of Chilmark.

Can I find studio apartments for rent in and around Chilmark?

Typically small in size, easy on the hip pocket and well located, it's easy to be charmed by a studio apartment. Get comfy in one of these vacation rentals and experience the vibe of Chilmark up close:

  • Explore the world around you and then sleep soundly at "Menemsha Village - Davis Cottage". This vacation rental is a popular base for sightseeing and comes with amenities including a phone and free WiFi.
  • Another inviting option is "Cozy Efficiency Apartment/heated Pool". Make use of air conditioning, WiFi and other convenient amenities during your stay.

There are plenty of sights around Chilmark to put on your to-do list. Feed your inner culture vulture by visiting SoWa Artists Guild and Artisans Asylum.

Can I find short term rentals in or near Chilmark?

Short-term rentals are plentiful in and around Chilmark. Stay a night or two in a luxury cabin, a budget apartment or a home that'll fit the family. Whatever type of property you're after, you'll find what you need with Vrbo. These are a few of our favorites:

  • Nice and close to the center of Chilmark, "Located Steps Away To Main Street And. 7 Miles From Surf Drive Beach" is the perfect place for a quick getaway. While you're about, don't miss top sights like Walden Pond and Louisa May Alcott's Orchard House.
  • Eat, sleep and explore from "Water View - Walk Town/beach, Pets Considered", another excellent option. Old Manse and Concord Visitors Center should be on your itinerary when it's time to see the sights.

What are the best romantic weekend getaways in or near Chilmark?

Whether spent in a luxury condo or a rustic cabin, a romantic weekend getaway is an excellent way to add some fire to your relationship. Whisk your other half away for a couple of leisurely days at one of these sought-after escapes in or near Chilmark:

  • Slip away on Friday afternoon for a few passion-filled nights at "Panoramic Views Of Snug Harbor In Beautiful West Falmouth". Approximately 18 miles from Chilmark, it comes with plenty of nice touches, like a fireplace and a nearby bay.
  • "Exceptional - Waterfront Home" is another retreat that'll impress. It's approximately 20 miles from Chilmark and has winery tours and beauty services.

What are the best large group vacation rentals in or near Chilmark?

Share your vacation and boost your odds of having fun. Whether you're planning an active getaway with buddies or a big family gathering, you'll have your choice of large group vacation rentals in and around Chilmark:

  • A range of amenities including a kitchen and a garden make "Panoramic Views Of Snug Harbor In Beautiful West Falmouth" a top pick for groups. This expansive getaway has 6 bedrooms and accommodates up to 12 guests. From the heart of Chilmark, it's around 18 miles away to the north.
  • Nothing's more important than being together with loved ones, and "Luxurious Estate Includes - Tennis Court" is the perfect place to do that. Located around 30 miles to the northeast of Chilmark, as many as 14 guests can stay in this vacation rental which has 6 bedrooms. A fireplace and a garden are among the various amenities you'll have at hand.

What are the best houses for rent with a pool in or near Chilmark?

Of all the amenities a vacation rental can offer, a pool is one of the most desired. Check out these houses for rent with a pool in or near Chilmark and spend your time splashing around. Just remember to bring your inflatable doughnut:

  • Round up your gang and enjoy a memorable stay at "New House, Steps To Beaches, Main St". There's plenty to love about this getaway apart from its pool, such as a fenced yard and childrens activities.
  • "Cool, Mid Century House - - Lots Of Light" is the kind of place you go to leave it all behind and make the most of your surroundings, starting with its pool. A stereo and a fridge are also on hand to make your visit as comfy as possible.

Not sure how to pack your suitcase for your Chilmark break? This enticing destination has a humid subtropical climate. In summer, you can expect average temperatures ranging from 65 ºF to 70 ºF. Scroll through our selection of Chilmark vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more great ideas about where to stay.

What are the best large family vacation rentals in or near Chilmark?

It's always more fun to share wonderful times with the folks you care about the most. Whether you're organizing a family get-together or getting away with close friends, we'll have a large vacation rental to suit your style. These are two of our best in and around Chilmark:

  • Get everyone under the same roof at "Panoramic Views Of Snug Harbor In Beautiful West Falmouth", which has 6 bedrooms that sleep up to 12 guests. This getaway is around 18 miles to the north of Chilmark and comes with amenities such as childrens activities and nearby whale-watching activities.
  • "Luxurious Estate Includes - Tennis Court" also offers the space you need to reconnect with loved ones. This rental is around 30 miles to the northeast of Chilmark, and accommodates as many as 14 guests in its 6 bedrooms. On-site watersports and childrens activities will help keep everyone content and comfortable.

If you're hoping to visit some family-friendly attractions around the area, there's no shortage of choice. New England Aquarium, Newbury Street and CoCo Key Water Resort - Boston promise lots of fun for all the gang.