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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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Seventh Heaven  - Vineyard Haven, MA Vacation Rental

Seventh Heaven

Vineyard Haven, MA
4 Bed 2 Bath Sleeps 9
- - - - 190 190 190 190 190 190 240 240 190 190 190 190 190
Nature's Pocket  - Vineyard Haven, MA Vacation Rental

Nature's Pocket

Vineyard Haven, MA
3 Bed 3 Bath Sleeps 6
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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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Bright Grove - Oak Bluffs, MA Vacation Rental

Bright Grove

Oak Bluffs, MA
3 Bed 2 Bath Sleeps 6
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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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Pine Street Haven - Edgartown, MA Vacation Rental

Pine Street Haven

Edgartown, MA
4 Bed 3 Bath Sleeps 8
140 145 140 - - - - 215 225 225 290 290 225 225 225 225 215
The Blue Cape - Edgartown, MA Vacation Rental

The Blue Cape

Edgartown, MA
3 Bed 2 Bath Sleeps 8
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The CAVU Mansion on Bellevue  - Tisbury, MA Vacation Rental
- - - - 185 185 195 195 195 195 250 250 195 195 195 195 195
Lantern Lane - Vineyard Haven, MA Vacation Rental

Lantern Lane

Vineyard Haven, MA
4 Bed 2.5 Bath Sleeps 11
180 185 185 235 235 195 195 195 195 195 250 250 195 195 195 195 195
Island Sanctuary - Oak Bluffs, MA Vacation Rental

Island Sanctuary

Oak Bluffs, MA
3 Bed 1.5 Bath Sleeps 7
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Casita del Amor "Love Cottage" - Edgartown, MA Vacation Rental
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Cape on Forest  - Oak Bluffs, MA Vacation Rental

Cape on Forest

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

Serenity

Oak Bluffs, MA
2 Bed 1.5 Bath Sleeps 4
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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
270 285 285 320 320 295 295 295 295 295 340 340 295 295 295 295 285
The Samoset  - Oak Bluffs, MA Vacation Rental

The Samoset

Oak Bluffs, MA
4 Bed 2 Bath Sleeps 8
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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 99 99 - - 115 120 120 120 120 160 160 120 120 115 - -
Oak View Cottage  - Oak Bluffs, MA Vacation Rental

Oak View Cottage

Oak Bluffs, MA
3 Bed 2.5 Bath Sleeps 6
- - - - 750 750 750 750 750 750 750 750 750 750 750 750 750
The Wayland Victorian - Oak Bluffs, MA Vacation Rental

The Wayland Victorian

Oak Bluffs, MA
5 Bed 2 Bath Sleeps 12
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Briar Patch - Edgartown, MA Vacation Rental

Briar Patch

Edgartown, MA
3 Bed 2 Bath Sleeps 7
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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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Colonial Blue on Whalers Walk - Edgartown, MA Vacation Rental
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Casa de Reyna - Edgartown, MA Vacation Rental

Casa de Reyna

Edgartown, MA
5 Bed 3.5 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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Stewart Manor - Oak Bluffs, MA Vacation Rental

Stewart Manor

Oak Bluffs, MA
3 Bed 2 Bath Sleeps 6
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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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Tranquility on Great Plains - West Tisbury, MA Vacation Rental
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Off the Radar on Hidden Village Road - West Tisbury, MA Vacation Rental
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Historic Whaling Captain's Home & Cottage - Falmouth, MA Vacation Rental
215 225 225 295 295 255 270 270 270 270 375 375 270 270 270 270 255
Beauty and the Beach on Chapoquoit Island  - Falmouth, MA Vacation Rental
- - - - - 195 195 195 195 195 290 - - - - 180 180
Historic Whaling Captain's Home - Falmouth, MA Vacation Rental
165 165 165 195 195 170 180 180 180 180 260 260 180 180 180 180 170
The Green Monstah! - Falmouth, MA Vacation Rental

The Green Monstah!

Falmouth, MA
4 Bed 1.5 Bath Sleeps 12
165 175 175 220 220 160 160 160 160 160 220 220 160 160 160 160 160
"Old Silver" - Falmouth, MA Vacation Rental

"Old Silver"

Falmouth, MA
2 Bed 1 Bath Sleeps 4
135 145 145 185 185 135 135 135 135 135 180 180 135 135 135 135 135
Captain's Cottage - Falmouth, MA Vacation Rental

Captain's Cottage

Falmouth, MA
1 Bed 1 Bath Sleeps 5
99 99 99 145 145 125 125 125 125 125 160 160 125 125 125 125 125
Mill View: La Maison de l'Artiste - Falmouth, MA Vacation Rental
135 145 145 185 185 145 145 145 145 145 190 190 145 145 145 145 145
A Slice of Heaven in Falmouth - Falmouth, MA Vacation Rental
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Stunning Coastal Retreat - Falmouth, MA Vacation Rental

Stunning Coastal Retreat

Falmouth, MA
5 Bed 2.5 Bath Sleeps 12
140 140 140 190 190 145 155 155 155 145 - - - - - - 140

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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