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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Spacious, Sunny, Private Chilmark Home

— Property 136112
Chilmark house rental - House with deck in back
4 Bedrooms, Sleeps 12,
House, 3 Bathrooms, near the ocean, rural, jacuzzi
Rates - per property (USD)
$3,500 - $4,500/week
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Spacious, High Ceilings, On Acre of Woods

— Property 106058
Chilmark house rental
1 Bedroom, Sleeps 2,
House, 1 Bathroom, pets considered, TV
Rates - per property (USD)
$1,450 - $1,650/week
Want to buy or sell a vacation home?
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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)
$2,000 - $3,850/week
$8,000 - $15,400/month
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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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The views will knock your socks off, Enjoy cooking in a gorgeous kitchen.

— Property 269558
Chilmark house rental - Snapping Turtle Farm entrance
5 Bedrooms, Sleeps 9,
House, 3 Bathrooms, near the ocean, waterfront, garden
Rates - per property (USD)
$3,000 - $11,000/week
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Secluded Contemporary, wooded, quiet, private- ferry tix available!

— 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
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Ocean View Chilmark Family Vacation Home. Walking distance to Squibnocket Beach.

— Property 278645
Chilmark house rental
5 Bedrooms, Sleeps 9,
House, 2 Bathrooms, 1 Half Bath, near the ocean, rural, internet access
Rates - per property (USD)
$2,500 - $9,000/week
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Exclusive Cobbs Hill Rd. Chilmark, Waterfront Tisbury Great Pond With Dock

— Property 230437
Chilmark house rental - View From Front Deck
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, beach, waterfront, balcony
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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
Rates - per property (USD)
$2,500 - $4,000/week
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Chilmark Cottage and studio, 5 acre privacy, wireless internet

— Property 120447
Chilmark cottage rental - 1
3 Bedrooms, Sleeps 6,
Cottage, 1 Bathroom, 1 Half Bath, near the ocean, rural, pets considered
Rates - per property (USD)
$1,450 - $2,450/week
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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
Rates - per property (USD)
$2,000 - $3,700/week
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ALDEN

— Property 7043684h
Chilmark house rental
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, internet access, pets
Rates - per house (USD)
$3,250 - $6,950/week
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HERGT

— Property 7043694h
Chilmark house rental
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, 1 Half Bath, internet access, dialup access
Rates - per house (USD)
$6,900 - $8,900/week
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HURLD

— Property 7043695h
Chilmark house rental
4 Bedrooms, Sleeps 8,
House, 1 Bathroom, 1 Half Bath, activity, adventure
Rates - per house (USD)
$4,500 - $6,500/week
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Waterfront: Tisbury Great Pond 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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Private beach, tennis courts, kayaks, very charming

— 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)
$800 - $1,300/week
Calendar Updated Feb 3 2010

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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Secluded Natural Chilmark House

— Property 117303
Chilmark house rental
2 Bedrooms, Sleeps 8,
House, 1 Bathroom, near the ocean, rural
Rates - per property (USD)
$475 - $1,500/week
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Prime Location in Chilmark w/Roof Deck Sunsets Over Menemsha- great for 2 groups

— Property 231734
Chilmark house rental - Main Deck Looking Towards House
3 Bedrooms, Sleeps 9,
House, 3 Bathrooms, near the ocean, rural, jacuzzi
Rates - per property (USD)
$3,500/week
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Sunset Water View, Hot Tub and Path to Menemsha Beach!

— Property 230932
Chilmark house rental - Peace glorious peace.
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, beach, near the ocean, garden
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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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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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Spring Point Waterview- CH216

— Property 7008400h
Chilmark house rental
3 Bedrooms, Sleeps 8,
House, 3 Bathrooms, 1 Half Bath, children welcome, pets not allowed
Rates - per house (USD)
$2,000 - $5,500/week
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Chilmark Retreat- CH205

— Property 7008387h
Chilmark house rental
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, coffee maker, children welcome
Rates - per house (USD)
$1,600 - $2,700/week
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Best View of the South Shore in Chilmark- CH209

— Property 7008391h
Chilmark house rental
4 Bedrooms, Sleeps 10,
House, 2 Bathrooms, 1 Half Bath, children welcome, pets not allowed
Rates - per house (USD)
$6,250 - $6,875/week
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Chilmark, Quansoo

— Property 7008393h
Chilmark house rental
2 Bedrooms, Sleeps 4,
House, 1 Bathroom, children welcome, pets not allowed
Rates - per house (USD)
$2,200/week
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Fabulous Waterview of Menemsha Pond

— Property 7008397h
Chilmark house rental
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, 1 Half Bath, coffee maker, children welcome
Rates - per house (USD)
$8,000/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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Large Chilmark house w/ocean views + private beach, cottage available too

— Property 164828
Chilmark house rental - House exterior facing ocean.
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, beach, rural, garden
Rates - per property (USD)
$2,995 - $5,250/week
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Chilmark Summer Home...small, luxury gem. private, convenient, fully equiptedem

— Property 114834
Chilmark house rental - Living room
3 Bedrooms, Sleeps 6,
House, 2 Bathrooms, 1 Half Bath, beach, village, internet access
Calendar Updated Jan 20 2010

Property Review

This was our 3rd year in Menemsha and the nicest vacation home we have stayed in. Very fair price; great layout; clean and spacious; wonderful yard (even with wild turkeys and roosters!) and a...