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Chilmark Vacation Rentals

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The  Eliot Noyes - Chilmark, MA Vacation Rental

The Eliot Noyes

Chilmark, MA
4 Bed 2 Bath Sleeps 8
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Sweet Island Child - Chilmark, MA Vacation Rental

Sweet Island Child

Chilmark, MA
3 Bed 2 Bath Sleeps 6
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The Bird's Nest  - Chilmark, MA Vacation Rental

The Bird's Nest

Chilmark, MA
2 Bed 1 Bath Sleeps 4
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Island Romance  - Chilmark, MA Vacation Rental

Island Romance

Chilmark, MA
4 Bed 1.5 Bath Sleeps 8
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The Looks Pond Garden House - West Tisbury, MA Vacation Rental
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Nature's Pocket  - Vineyard Haven, MA Vacation Rental

Nature's Pocket

Vineyard Haven, MA
3 Bed 3 Bath Sleeps 6
265 280 330 330 295 295 295 295 295 350 350 295 295 295 295 295 350
Cape on Forest  - Oak Bluffs, MA Vacation Rental

Cape on Forest

Oak Bluffs, MA
4 Bed 2 Bath Sleeps 8
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The Walker House  - Oak Bluffs, MA Vacation Rental

The Walker House

Oak Bluffs, MA
4 Bed 2 Bath Sleeps 8
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Bright Grove - Oak Bluffs, MA Vacation Rental

Bright Grove

Oak Bluffs, MA
3 Bed 2 Bath Sleeps 6
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Seventh Heaven  - Vineyard Haven, MA Vacation Rental

Seventh Heaven

Vineyard Haven, MA
4 Bed 2 Bath Sleeps 9
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Tranquility on Great Plains - West Tisbury, MA Vacation Rental
155 165 215 215 175 175 175 175 175 225 225 175 175 175 175 175 225
Pine Street Haven - Edgartown, MA Vacation Rental

Pine Street Haven

Edgartown, MA
4 Bed 3 Bath Sleeps 8
130 130 - - - - - - - 215 225 160 160 160 160 160 225
The Happy Place  - Vineyard Haven, MA Vacation Rental

The Happy Place

Vineyard Haven, MA
4 Bed 1.5 Bath Sleeps 8
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Casita del Amor "Love Cottage" - Edgartown, MA Vacation Rental
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The CAVU Mansion on Bellevue  - Tisbury, MA Vacation Rental
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Oak Villa - Edgartown, MA Vacation Rental

Oak Villa

Edgartown, MA
6 Bed 3.5 Bath Sleeps 13
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The Blue Cape - Edgartown, MA Vacation Rental

The Blue Cape

Edgartown, MA
3 Bed 2 Bath Sleeps 8
115 120 180 180 125 125 125 135 135 195 195 135 135 135 135 135 195
Colonial Blue on Whalers Walk - Edgartown, MA Vacation Rental
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Islander's Retreat  - Vineyard Haven, MA Vacation Rental

Islander's Retreat

Vineyard Haven, MA
3 Bed 3.5 Bath Sleeps 9
270 285 320 320 295 295 295 295 295 340 340 295 295 295 295 295 340
Lantern Lane - Vineyard Haven, MA Vacation Rental

Lantern Lane

Vineyard Haven, MA
4 Bed 2.5 Bath Sleeps 11
180 180 235 235 195 195 195 195 195 250 250 195 195 195 195 195 250
Briar Patch - Edgartown, MA Vacation Rental

Briar Patch

Edgartown, MA
3 Bed 2 Bath Sleeps 7
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Serenity  - Oak Bluffs, MA Vacation Rental

Serenity

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 4
120 130 160 160 135 135 135 135 135 170 170 135 135 135 135 135 170
Island Sanctuary - Oak Bluffs, MA Vacation Rental

Island Sanctuary

Oak Bluffs, MA
3 Bed 1.5 Bath Sleeps 7
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The Wayland Victorian - Oak Bluffs, MA Vacation Rental

The Wayland Victorian

Oak Bluffs, MA
5 Bed 2 Bath Sleeps 12
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Oak View Cottage  - Oak Bluffs, MA Vacation Rental

Oak View Cottage

Oak Bluffs, MA
3 Bed 2.5 Bath Sleeps 6
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The Vacation House - Vineyard Haven, MA Vacation Rental

The Vacation House

Vineyard Haven, MA
2 Bed 1 Bath Sleeps 6
- 99 145 145 115 115 115 115 115 155 155 115 115 115 115 115 155
Casa de Reyna - Edgartown, MA Vacation Rental

Casa de Reyna

Edgartown, MA
5 Bed 3.5 Bath Sleeps 8
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The Samoset  - Oak Bluffs, MA Vacation Rental

The Samoset

Oak Bluffs, MA
4 Bed 2 Bath Sleeps 8
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Sunset Meadows - Oak Bluffs, MA Vacation Rental

Sunset Meadows

Oak Bluffs, MA
2 Bed 1 Bath Sleeps 4
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Martha's Nest - Edgartown, MA Vacation Rental

Martha's Nest

Edgartown, MA
3 Bed 2 Bath Sleeps 8
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Off the Radar on Hidden Village Road - West Tisbury, MA Vacation Rental
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Captain's Cottage - Falmouth, MA Vacation Rental

Captain's Cottage

Falmouth, MA
1 Bed 1 Bath Sleeps 5
99 99 150 150 115 115 115 160 160 195 195 160 160 160 160 160 195
"Old Silver" - Falmouth, MA Vacation Rental

"Old Silver"

Falmouth, MA
2 Bed 1 Bath Sleeps 4
120 130 170 170 135 135 135 160 160 195 195 160 160 160 160 160 195
Beauty and the Beach on Chapoquoit Island  - Falmouth, MA Vacation Rental
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The Green Monstah! - Falmouth, MA Vacation Rental

The Green Monstah!

Falmouth, MA
4 Bed 1.5 Bath Sleeps 12
195 220 255 255 235 235 235 185 185 235 235 185 185 185 185 185 235
Stunning Coastal Retreat - Falmouth, MA Vacation Rental

Stunning Coastal Retreat

Falmouth, MA
5 Bed 2.5 Bath Sleeps 12
140 140 175 175 145 155 155 160 160 225 215 - - - - - -
Historic Whaling Captain's Home - Falmouth, MA Vacation Rental
700 700 700 700 700 700 700 700 700 700 700 700 700 700 700 700 700
Mill View: La Maison de l'Artiste - Falmouth, MA Vacation Rental
120 130 170 170 135 135 135 135 135 180 180 135 135 135 135 135 180
Historic Whaling Captain's Home & Cottage - Falmouth, MA Vacation Rental
750 750 750 750 750 750 750 750 750 750 750 750 750 750 750 750 750
A Slice of Heaven in Falmouth - Falmouth, MA Vacation Rental
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About Chilmark

Chilmark rated 4.8 out of 5 based on 5 reviews Chilmark, MA

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. 

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. 

Photo credit: Massachusetts Office of Travel and Tourism via flickr

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