Chilmark Vacation Rentals

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USA > Massachusetts > Chilmark

Make Chilmark your next getaway—choose from 8 great vacation rentals

A quiet residential town that includes nearby Nomans Land Island, Chilmark, Massachusetts is a haven of rest and relaxation. It's no wonder President Obama and his family are frequent visitors to this quiet stretch of Martha's Vineyard! Stroll by a variety of small ponds or relax amid the wildflowers at one of the preserves. You'll find out soon enough why everyone wants to stay at one of our Chilmark vacation rentals when they head to this bucolic wonder. 

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House rentals

View 8 House rentals

Chilmark vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Chilmark Charm
2 Bedroom | 1 Bath | Sleeps 4

Chilmark Charm - Chilmark, MA

$341 avg / night
Hillside Oak
4 Bedroom | 4 Bath | Sleeps 8

Hillside Oak - Chilmark, MA

$591 avg / night
Chilmark Beauty
5 Bedroom | 2 Bath | Sleeps 8

Chilmark Beauty - Chilmark, MA

$443 avg / night
North Road Home
3 Bedroom | 2.5 Bath | Sleeps 6

North Road Home - Chilmark, MA

$355 avg / night
The Eliot Noyes
4 Bedroom | 2 Bath | Sleeps 8

The Eliot Noyes - Chilmark, MA

$794 avg / night

View 3 more homes

Recent Chilmark vacation rental reviews

We loved staying in this Chilmark charmer. Unlike other rentals we have had on the Vineyard, everything here is new, fresh, clean, modern, bright, airy and comfortable at the same time. The rooms are spacious, with many nice design touches. The bathroom is large, has a great shower and has high quality finishes. The closets have plenty of room for your gear. The mattresses are new and very comfortable. The appliances and heat and AC are all new and work well. There are plenty of places to hike and walk right outside your door. All this, in a lovely wooded setting with a pretty backyard. We will be back!
Karen K. | Sep 2022
I booked this house because it had a pool and it did not disappoint us! My family had a great time playing in the pool. It was so nice to jump in after a hot day being out and about. I was a bit concerned about not having AC but it wasn’t bad at all.
Jin A. | Aug 2022
The views, area, environment and culture all make it worth every penny!
Dan G. | Jun 2022
Chilmark Frequently Asked Questions

Yes, 6 of our Chilmark homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 26 of our Chilmark vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Chilmark vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Chilmark team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Chilmark, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

History of Chilmark, MA

Europeans settled the area in 1660 and the town became its own entity in 1714. It has long been a farming community and, at one point in the 1800s, boasted 96 working farms. Mariners also called it home due to its beautiful meadows and plentiful green spaces. Today, it remains quiet and peaceful, with few bustling businesses. It's a place to truly get away from the everyday!

Things to do in Chilmark

Chilmark is known for its tranquility and natural wonders. The beaches get the most draw in the summer, although it's important to note that most beaches are reserved for residents only and require seasonal passes. Luckily, the town has one fully public beach that doesn't require a pass. Leave your worries behind and head to Menemsha Beach, on the North Shore of the island. It's perfect for the entire family thanks to its gentle waves and clean water. 

The town's ponds also lure tourists looking for scenic spots to contemplate life. Tisbury Great Pond, Menemsha Pond, and Squibnocket Pond are all popular spots during the summer for late afternoon strolls. Head to Peaked Hill, the tallest point on the island - 311 feet - for a great view of the area. 

There are several nature preserves that shouldn't be missed! Menemsha Hills Reservation is a hiker's dream. You can head up to the second-tallest peak on the island, through wetlands and woodlands, and enjoy spectacular ocean views at this 211-acre preserve. Don't forget your fishing rod as you're more than welcome to surfcast here!

The Waskosim's Rock Reservation is great for hikers and bikers who can traverse woodland, open fields, and wetland at this 185-acre preserve. The Fulling Mill Brook Conservation Area is worthy of a detour due to its variety of activities, from hiking to picnicing to horseback riding. The 50-are preserve boasts nesting songbirds and numerous footbridges over babbling brooks. 

Day Trips from Chilmark

While Chilmark is a great place to explore, you should spend an afternoon venturing out of town and seeing all the other great spots on the Vineyard! West Tisbury has the 60-acre Polly Hill Arboretum. Vineyard Haven is known for the Long Point Wildlife Refuge, as well as number of mom-and-pop shops. Edgartown has the peaceful Cape Pogue Wildlife Refuge and the Felix Neck Wildlife Sanctuary. Ride the country's oldest carousel in Oaks Bluff or visit the historic East Chop Lighthouse. 

Beauty and tranquility peacefully collide in lovely Chilmark! Book a Chilmark vacation rental today to see for yourself why the Obamas and others love this quiet Massachusetts town.