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Chilmark Vacation Rentals

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Enjoy blissful beaches at a Chilmark vacation home

Vacation homes in Chilmark, Massachusetts, snuggle between Providence, Boston, and internationally famous natural beauty spots such as Martha's Vineyard. With a vacation home here, you can enjoy some of the finest cultural and intellectual scenes in the country as well as the state's superlatively beautiful coastline.

Save up to 50%

Best Vacation Home Deals in Chilmark

Oct 21 - Oct 28

-35%

~~$1,072~~

$700 per night

House ∙ 12 guests ∙ 4 bedrooms

Vacation Home in Chilmark with Yard & Grill

5.0

"Excellent" (44 ratings)

Chilmark, Dukes County, Massachusetts, United States

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Oct 21 - Oct 28

-46%

~~$929~~

$500 per night

House ∙ 14 guests ∙ 5 bedrooms

Lovely Vacation Home in Menemsha with Grill & Yard + Distant Views

4.4

"Very good" (37 ratings)

Chilmark, Dukes County, Massachusetts, United States

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Jun 18 - Jun 25

-50%

~~$425~~

$214 per night

House ∙ 8 guests ∙ 4 bedrooms

House in Menemsha with Grill

4.5

"Outstanding"

Chilmark, Dukes County, Massachusetts, United States

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Vacasa

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Find the ideal vacation rental for as little as $214 per night by searching among the 118 options being offered in Chilmark. With HomeToGo, you can directly compare the prices of each available property to find the best price and save up to 51%.

Book Vacation Rental Offers with the Highest User Rating

Top-Rated Rentals and Accommodations in Chilmark

Sep 23 - Sep 30

$715 per night

House ∙ 6 guests ∙ 4 bedrooms

Vacation Home in Menemsha with Yard & Grill + Water Views

5.0

"Excellent" (14 ratings)

Chilmark, Dukes County, Massachusetts, United States

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Oct 21 - Oct 28

$800 per night

Cottage ∙ 5 guests ∙ 2 bedrooms

Cottage in Chilmark with Grill + Beach Nearby

5.0

"Excellent" (6 ratings)

Chilmark, Dukes County, Massachusetts, United States

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Jan 8 - Jan 15

$243 per night

House ∙ 8 guests ∙ 4 bedrooms

Beautiful Vacation Home in Menemsha with Grill + Ocean View

4.5

"Outstanding"

Chilmark, Dukes County, Massachusetts, United States

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Vacasa

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Recommended Vacation Rentals in Chilmark

Find your perfect vacation rental in Chilmark: from $214 per night

May 25 - Jun 1

$375 per night

House ∙ 3 guests ∙ 2 bedrooms

Nice Vacation Home in Menemsha with Grill & Yard

5.0

"Excellent" (36 ratings)

Chilmark, Dukes County, Massachusetts, United States

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Jun 17 - Jun 24

-47%

~~$434~~

$230 per night

House ∙ 8 guests ∙ 4 bedrooms

Pleasant Vacation Home in Menemsha with Grill

4.6

"Outstanding" (5 ratings)

Chilmark, Dukes County, Massachusetts, United States

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Dec 2 - Dec 9

-41%

~~$396~~

$235 per night

House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Menemsha with Grill & Yard + 180-Degree View

5.0

"Excellent" (2 ratings)

Chilmark, Dukes County, Massachusetts, United States

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Oct 21 - Oct 28

$437 per night

House ∙ 4 guests ∙ 2 bedrooms

House in Menemsha with Yard & Grill + Pond Views

5.0

"Excellent" (20 ratings)

Chilmark, Dukes County, Massachusetts, United States

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Oct 21 - Oct 28

$370 per night

Cottage ∙ 5 guests ∙ 2 bedrooms

Rustic Cottage in Menemsha with Grill & Yard + Water Views

5.0

"Excellent" (9 ratings)

Chilmark, Dukes County, Massachusetts, United States

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Oct 21 - Oct 28

-42%

~~$1,200~~

$700 per night

House ∙ 8 guests ∙ 3 bedrooms

Modern Vacation Home in Menemsha with Grill + Close to Beach

5.0

"Excellent" (20 ratings)

Chilmark, Dukes County, Massachusetts, United States

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Sep 23 - Sep 30

-22%

~~$460~~

$358 per night

House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Menemsha with Grill & Yard

4.8

"Excellent" (8 ratings)

Chilmark, Dukes County, Massachusetts, United States

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May 25 - Jun 1

$405 per night

House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Menemsha with Grill & Yard

4.9

"Excellent" (42 ratings)

Chilmark, Dukes County, Massachusetts, United States

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Dec 2 - Dec 9

$500 per night

Cottage ∙ 7 guests ∙ 3 bedrooms

Nice Cottage in Menemsha with Yard + Water Views

5.0

"Excellent" (2 ratings)

Chilmark, Dukes County, Massachusetts, United States

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Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals in Chilmark

May 25 - Jun 1

$565 per night

Cottage ∙ 6 guests ∙ 3 bedrooms

Charming Cottage in Menemsha with Grill & Yard

Chilmark, Dukes County, Massachusetts, United States

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Sep 23 - Sep 30

$950 per night

House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Menemsha with Yard, Grill & Pool

5.0

"Excellent" (23 ratings)

Chilmark, Dukes County, Massachusetts, United States

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Aug 19 - Aug 26

$1,200 per night

House ∙ 6 guests ∙ 3 bedrooms

Pleasant House in Chilmark with Grill & Yard + Wonderful Views

5.0

"Excellent" (21 ratings)

Chilmark, Dukes County, Massachusetts, United States

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Vacation Houses With Pools

Make a splash on your next vacation! Over 9% of in Chilmark vacation rentals have a swimming pool.

May 11 - May 18

-42%

~~$989~~

$571 per night

House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Menemsha with Yard, Grill & Pool

5.0

"Excellent" (23 ratings)

Chilmark, Dukes County, Massachusetts, United States

Pool

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Feb 24 - Mar 2

$999 per night

House ∙ 4 guests ∙ 4 bedrooms

Vacation Home in Menemsha with Gunite Pool

5.0

"Excellent" (4 ratings)

Chilmark, Dukes County, Massachusetts, United States

Pool

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Jul 1 - Jul 8

$1,000 per night

House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Chilmark with Pool & Grill + Beautiful View

Chilmark, Dukes County, Massachusetts, United States

Pool

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WeNeedaVacation

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Dog-Friendly Vacation Rentals

Bring Fido on your next trip and book a stay in one of these pet-friendly rentals in Chilmark!

Nov 4 - Nov 11

-21%

~~$376~~

$296 per night

House ∙ 3 guests ∙ 2 bedrooms

Nice Vacation Home in Menemsha with Grill & Yard

5.0

"Excellent" (36 ratings)

Chilmark, Dukes County, Massachusetts, United States

Pet-friendly

Details

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Dec 16 - Dec 23

-42%

~~$391~~

$227 per night

House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Menemsha with Grill & Yard + 180-Degree View

5.0

"Excellent" (1 rating)

Chilmark, Dukes County, Massachusetts, United States

Pet-friendly

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Nov 4 - Nov 11

-19%

~~$437~~

$356 per night

House ∙ 4 guests ∙ 2 bedrooms

House in Menemsha with Yard & Grill + Pond Views

5.0

"Excellent" (19 ratings)

Chilmark, Dukes County, Massachusetts, United States

Pet-friendly

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Best vacation rentals with a balcony

Looking for a home with a balcony? Check out these vacation homes in Chilmark with their own private patios and balconies.

Oct 21 - Oct 28

-46%

~~$930~~

$500 per night

House ∙ 14 guests ∙ 5 bedrooms

Lovely Vacation Home in Menemsha with Grill & Yard + Distant Views

4.4

"Very good" (37 ratings)

Chilmark, Dukes County, Massachusetts, United States

Balcony

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Oct 21 - Oct 28

$1,348 per night

House ∙ 10 guests ∙ 4 bedrooms

House in Menemsha with Yard & Grill + Water View

5.0

"Excellent" (11 ratings)

Chilmark, Dukes County, Massachusetts, United States

Balcony

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Jun 3 - Jun 10

-33%

~~$1,500~~

$1,000 per night

House ∙ 6 guests ∙ 3 bedrooms

Nice Vacation Home in Menemsha with Grill + Great Views

Chilmark, Dukes County, Massachusetts, United States

Balcony

Details

WeNeedaVacation

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Popular Rental Amenities in Chilmark

Pets allowed (43)
Air conditioning (90)
Pool (11)
Internet (123)
TV (110)
Fireplace (51)
Grill (114)
Balcony/Patio (4)
Washer (107)
Microwave (104)
Parking (3)
Kitchen (123)

Use filters to look for an offer fitting your needs among all of the rentals in Chilmark. You can easily search and find a vacation rental fitting your criteria in Chilmark if you travel with your pet or you would prefer a rental with A/C, as most accommodations provide "Pets allowed" and "Air conditioning." It is also possible to find a property in Chilmark if you need a special entrance for wheelchairs as 4 of the listed accommodations there offer "Wheelchair accessible."

The Weather in Chilmark

- Rainy days

Check out the climate diagram for Chilmark. In July maximum temperatures go higher than 81°. Conversely, February is the coolest month in Chilmark, with temperatures going under 25° The rainiest month is January while the driest month is August.

7-Day Weather Forecast in Chilmark

Sun, 4 Jun

50°

48°

Mon, 5 Jun

57°

53°

Tue, 6 Jun

66°

55°

Wed, 7 Jun

62°

55°

Thu, 8 Jun

59°

55°

Fri, 9 Jun

62°

57°

Sat, 10 Jun

64°

57°

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Accommodations for your vacation in Chilmark

In Chilmark, most of the 118 accommodation types are house rental, which represent 89.47% of its listed properties. Interestingly, specific accommodation type, this specific type of property is $1,611 a night, with an average area of 194 m². Moreover, if you are going in a group of 7, house rental are the ideal property type in Chilmark, as they usually welcome this exact group size. If you would prefer to book a different accommodation type, you could consider cabin, which are the other most frequent property type in Chilmark. Cabin in Chilmark are 105 m² on average, with prices averaging $663 per night.

What are the best places to discover the arts and culture of Chilmark?

Hang out at Edgar Allen Poe’s old haunts

Providence sits at the confluence of several rivers – fitting, as it is also a confluence of culture. While Boston has Harvard, Providence is home to Brown University, another prominent Ivy League institution. Its historic streets are filled with charming lanes, galleries, and theaters where you can experience the latest outpourings from creative locals. Rhode Island School of Design is also situated here, and the Providence Athenaeum's unique architecture is not to be missed. The famously eccentric poet Edgar Allen Poe allegedly used to pursue women here!

What are the best activities for families in Chilmark?

Into the wild

Children love the animals at Nomans Land Island National Wildlife Center. Approximately 640 acres of island stretch before you, full of exciting wildlife such as raptors, songbirds, and double-crested cormorants. Wander the trails through goldenrod and American beachgrass as you take in the views. Martha's Vineyard, a charming enclave that attracts creatives, is miles away from the grip of commercialization. Menemsha Harbor, featured in the film Jaws, is ringed with fishing boats and sublime views over the sparkling water.

Where are the unique attractions in Chilmark?

Venture to Boston

Boston, just a two-and-a-half-hour drive along the coast from your vacation home, is well worth the journey. With Harvard University, the Boston Tea Party Ships & Museum, and Boston Public Library all vying for your attention, you'll be glad you came. Watch the Red Sox play at Fenway Park in the summer months, or head to MIT to see some of the world's most famous innovations. The intellectual scope of the city is matched only by its architectural elegance.

Information about vacation rentals in Chilmark

🏡 Vacation rentals	118 properties
💳 Possible discounts	up to 51%
🌙 Nightly prices starting at	$214
⭐ Popular amenities	Pets allowed, Air conditioning and Pool
🐾 Pet friendly accommodations	42 properties
🏊 Vacation rentals with pools	10 properties

Frequently Asked Questions

What is the nightly price for a vacation home in Chilmark?

The average accommodation in Chilmark is priced at $214 per night. If you would like to stay in a house rental, the average price is $1,611 per night. A cabin Chilmark will cost $663 per night on average.

How many vacation rentals are available to book in Chilmark?

There are 118 vacation homes in Chilmark to browse and rent for your next trip.

What are the most popular amenities for vacation rentals in Chilmark?

Three most popular amenities for home rentals in Chilmark include accommodations that have: Pets allowed, Air conditioning, and Pool.

How many vacation homes with a pool are in Chilmark?

Choose from 10 vacation rentals available in Chilmark.

Are dogs allowed in vacation rentals in Chilmark?

Sure, currently there are 42 vacation rentals in Chilmark that allow dogs and the average nightly rate is $1,925.

What's the best time of year to travel to Chilmark?

July and August are the warmest months in Chilmark with temperatures around 81 °F. The coldest months in Chilmark are February and January, with 25 °F on average.

We list offers from thousands of providers, including:

max. Min. 41° 27° 16 days 16	max. Min. 39° 25° 15 days 15	max. Min. 46° 28° 15 days 15	max. Min. 57° 37° 13 days 13	max. Min. 66° 48° 13 days 13	max. Min. 73° 55° 11 days 11	max. Min. 81° 64° 11 days 11	max. Min. 79° 61° 9 days 9	max. Min. 75° 54° 9 days 9	max. Min. 64° 46° 13 days 13	max. Min. 54° 37° 10 days 10	max. Min. 48° 34° 16 days 16
Jan.	Feb.	Mar.	Apr.	May	June	July	Aug.	Sep.	Oct.	Nov.	Dec.

Chilmark Vacation Rentals

Choose the perfect vacation rental

Enjoy blissful beaches at a Chilmark vacation home

Best Vacation Home Deals in Chilmark

Top-Rated Rentals and Accommodations in Chilmark

Recommended Vacation Rentals in Chilmark

Budget-friendly Vacation Rentals in Chilmark

Vacation Houses With Pools

Dog-Friendly Vacation Rentals

Best vacation rentals with a balcony

Popular Rental Amenities in Chilmark

The Weather in Chilmark

7-Day Weather Forecast in Chilmark

Accommodations for your vacation in Chilmark

Hang out at Edgar Allen Poe’s old haunts

Into the wild

Venture to Boston

Information about vacation rentals in Chilmark

Frequently Asked Questions

What is the nightly price for a vacation home in Chilmark?

How many vacation rentals are available to book in Chilmark?

What are the most popular amenities for vacation rentals in Chilmark?

How many vacation homes with a pool are in Chilmark?

Are dogs allowed in vacation rentals in Chilmark?

What's the best time of year to travel to Chilmark?

Vacation Destinations Near Chilmark

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