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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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. 25 of our Chilmark vacation rentals have internet access, so you can stay connected throughout your trip.Browse homes with internet access >
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 >
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!
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.
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.