Book a Chilmark Rental for a Perfect Massachusetts Getaway

When you think of a Massachusetts vacation, Martha’s Vineyard probably comes to mind. Chilmark is on the western coast of the island and is often referred to as “up-island” by the locals. It is known for its stone walls, rolling meadows, and one of the best beaches on the island, Lucy Vincent Beach. Chilmark also has the highest property values in the state, which makes a Chilmark rental quite prestigious.

Chilmark Vacation Rentals in a Fishing Village


With Chilmark rentals, it is possible to take in the rustic charm of Menemsha, a small fishing village opening up to the Vineyard Sound. It was in this village that much of the film “Jaws” was shot. Local fishermen and visitors from Chilmark vacation rentals alike take advantage of the well-populated waters. Visitors to a Chilmark rental may charter a fishing boat or visit Dutcher’s Dock for a plethora of fresh fish markets.

Best Beach Offered to Chilmark Rentals


Lucy Vincent Beach is one of the best beaches available to those who stay in Chilmark rentals. It is a private beach, intended for island residents only, but if you have a Chilmark rental, this won’t be a problem as you can get the proper identification issued at the city hall. The popular beach may shock some people who stay in Chilmark vacation rentals as nudity is allowed, so just be advised when you arrive!

With a Chilmark Rental, There’s Plenty to Do


With a Chilmark rental, you don’t have to stay right in town. Martha’s Vineyard is small enough that you can visit each small town on a different day and still enjoy your time at your Chilmark rentals in the evening. There are plenty of antique shops and specialty stores to fill your days after beach bumming and eating! Chilmark vacation rentals allow for a true Massachusetts getaway and are perfect for three-day weekends or a week in the summer.

Increase your search options for Martha's Vineyard lodging in the following areas: vacation rentals in Chappaquiddick, lodging in Edgartown MA, Katama beach homes, Vineyard Haven home rental, or vacation accommodation West Tisbury MA.



Vacation Rentals Chilmark Massachusetts

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Private, Chilmark, Architect Designed & Owned, serene

— Property 239624
Chilmark house rental - Front Exterior View Showing Full Veranda
3 Bedrooms, Sleeps 8,
House, 3 Bathrooms, near the ocean, rural, garden
Rates - per property (USD)
$2,500 - $3,850/week
$10,000 - $15,400/month
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North and South Shore Waterviews

— Property 7015682h
Chilmark house rental - North Shore Views from Main House
5 Bedrooms, Sleeps 10,
House, 3 Bathrooms, beach, clothes dryer
Rates - per house (USD)
$25,714/month
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Privacy, Serenity, Elegance, Beautiful Sunrise Views, Chilmark

— Property 238938
Chilmark house rental
2 Bedrooms, Sleeps 4,
House, 1 Bathroom, near the ocean, rural, garden
Rates - per property (USD)
$1,750 - $2,600/week
$7,000 - $10,400/month
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Exclusive Cobbs Hill Rd. Chilmark Waterfront Tisbury Great Pond

— Property 230437
Chilmark house rental - View From Front Deck
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, beach, waterfront, balcony
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Waterfront: Ten acres in Quansoo With QBA Beach Key-Main & Guest Houses

— Property 107871
Chilmark house rental - View from sun room to pond and beach beyond
4 Bedrooms, Sleeps 10,
House, 3 Bathrooms, rural, waterfront, internet access
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Waterview, Air-Conditioned, totally private setting w/ large yard

— Property 133117
Chilmark house rental - 3 acre privacy, wrap-around decks
4 Bedrooms, Sleeps 8,
House, 2 Bathrooms, near the ocean, rural, garden
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Waterview, Newly Renovated Tri-Level

— Property 121220
Chilmark house rental - just driving in,large private yard in front
4 Bedrooms, Sleeps 9,
House, 3 Bathrooms, near the ocean, rural, internet access
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Key to Black Point Beach, 5-acre privacy, located in Quansoo

— Property 120243
Chilmark house rental - courtyard area, round outside shower
4 Bedrooms, Sleeps 8,
House, beach, rural, garden
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Chilmark Cottage and studio, 5 acre privacy, wireless internet

— Property 120447
Chilmark cottage rental - close-up of front deck and brick sidepatio
3 Bedrooms, Sleeps 6,
Cottage, 1 Bathroom, 1 Half Bath, near the ocean, rural, pets considered
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Menemsha Harbor, Magical Cottage with Panoramic Sunset and Water Views

— Property 133101
Chilmark cottage rental - waterside and front of cottage
3 Bedrooms, Sleeps 4,
Cottage, 1 Bathroom, 1 Half Bath, beach, near the ocean, TV
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Air-Conditioned, Vineyard and St.Bart's Blend, completely private setting

— Property 134537
Chilmark house rental - front yard, fully decked, MBR to right
3 Bedrooms, Sleeps 6,
House, near the ocean, rural, garden
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Chilmark Waterview Compound w/ Pool

— Property 219166
Chilmark house rental
5 Bedrooms, Sleeps 13,
House, 3 Bathrooms, beach, near the ocean, pool
Calendar Updated Nov 10 2009

Property Review

We rented this house last summer with our family, including small children. We were very disapointed at the condition of the house and property. There were piles of trash with nails and broken...
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Sea Watch

— Property 204164
Chilmark house rental
5 Bedrooms, Sleeps 12,
House, beach, near the ocean, jacuzzi
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Beetlebung Cottage

— Property 218759
Chilmark cottage rental
2 Bedrooms, Sleeps 6,
Cottage, 1 Bathroom, 1 Half Bath, beach, river, garden
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Log Cabin

— Property 204169
Chilmark cottage rental
Studio, Sleeps 6,
Cottage, beach, river, garden
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Charming Menemsha Harbor Cottage

— Property 253913
Chilmark house rental - Sunset house & Menemsha Creek
3 Bedrooms, Sleeps 6,
House, 1 Bathroom, beach, near the ocean, satellite or cable
Rates - per property (USD)
$1,200 - $2,300/week
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Martha's Vineyard - Chilmark cottage

— Property 246898
Chilmark cottage rental
2 Bedrooms, Sleeps 4,
Cottage, 1 Bathroom, beach, near the ocean, garden
Rates - per property (USD)
$750 - $1,300/week
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Charming cape on Upper Chilmark Pond and Lucy Vincent Beach

— Property 224786
Chilmark house rental - Living Room / Dining Room
3 Bedrooms, Sleeps 7,
House, 2 Bathrooms, beach, waterfront, internet access
Rates - per property (USD)
$7,000 - $12,500/week
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Stunning Views and Sunsets

— Property 182266
Chilmark cottage rental - View toward Menemsha
3 Bedrooms, Sleeps 8,
Cottage, 3 Bathrooms, beach, waterfront, garden
Rates - per property (USD)
$2,600 - $5,300/week
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Spacious, Conveniently Located Saltbox in Chilmark -

— Property 106032
Chilmark house rental - Welcome!
4 Bedrooms, Sleeps 8,
House, 2 Bathrooms, near the ocean, rural, internet access
Rates - per property (USD)
$1,000 - $2,950/week
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Private beach, tennis courts, kayaks, very charming: Seasonal Rental

— Property 165500
Chilmark studio rental - Abel's Hill private beach
1 Bedroom, Sleeps 2,
Studio, beach, near the ocean, tennis court
Rates - per property (USD)
$5,000/month
Calendar Updated Oct 24 2009

Property Review

A perfect casual getaway...The living space, beach, and amenities (e.g., kayaks, grill, outdoor seating) were perfect for two. Note that the pictures do not do the studio's size or feel justice;...
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Charming Yankee Barn in Martha's Vineyard pristine Chilmark area

— Property 116157
Chilmark house rental
4 Bedrooms, Sleeps 8,
House, 2 Bathrooms, 1 Half Bath, beach, rural, pets considered
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House Rental, Chilmark, Mass. - Menemsha Pond Views with Private Beach Access

— Property 259557
Chilmark house rental - Cove Road House
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, beach, near the ocean, garden
Rates - per property (USD)
$3,500/week
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Sunny, hilltop home with treetop view

— Property 187239
Chilmark house rental - Welcome!
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, near the ocean, resort, air-conditioning
Rates - per property (USD)
$3,000 - $3,500/week
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Charming Chilmark Cottage

— Property 234463
Chilmark cottage rental
2 Bedrooms, Sleeps 5,
Cottage, 2 Bathrooms, near the ocean, rural, internet access
Rates - per property (USD)
$1,700 - $2,200/week
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Secluded Chilmark summer house with sweeping Atlantic views

— Property 164828
Chilmark house rental - House exterior facing ocean.
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, near the ocean, rural, garden
Rates - per property (USD)
$4,990 - $5,600/week
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Stone Walls, Flowery Meadows, Ocean View, newly rennovated cottage

— Property 119314
Chilmark house rental
3 Bedrooms, Sleeps 5,
House, 1 Bathroom, 1 Half Bath, near the ocean, rural, garden
Rates - per property (USD)
$2,800/week
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Recession Special/Prime Location in Chilmark With Sunsets Over Menemsha Pond

— Property 231734
Chilmark house rental - Main Deck Looking Towards House
3 Bedrooms, Sleeps 9,
House, 3 Bathrooms, near the ocean, rural, jacuzzi
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Desirable Chilmark Location Sweeping Ocean Views Private Beach

— Property 194085
Chilmark house rental - View from deck and living area
4 Bedrooms, Sleeps 8,
House, 2 Bathrooms, beach, near the ocean, tennis court
Rates - per property (USD)
$3,000 - $4,000/week
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Secluded Contemporary, wooded, quiet, private

— Property 106205
Chilmark house rental
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, near the ocean, rural, balcony
Rates - per property (USD)
$2,200 - $2,600/week