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Chilmark Vacation Rentals

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Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Farmhouse
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

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.

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Best Vacation Home Deals in Chilmark

House 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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Vrbo
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House Chilmark
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
Details
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House Chilmark
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
Details
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%.

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Top-Rated Rentals and Accommodations in Chilmark

House 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
Details
Vrbo
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Cottage Chilmark
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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House Chilmark
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
Details
Vacasa
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Recommended Vacation Rentals in Chilmark

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

House Chilmark
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
Details
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House Chilmark
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
Details
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House Chilmark
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
Details
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House Chilmark
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
Details
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Cottage Chilmark
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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House Chilmark
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
Details
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House Chilmark
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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House Chilmark
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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Cottage Chilmark
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

Cottage 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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House Chilmark
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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House Chilmark
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.

House Pool Chilmark
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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House Pool Chilmark
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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House Pool Chilmark
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!

House Pet-friendly 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
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House Pet-friendly Chilmark
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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House Pet-friendly Chilmark
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.

House Balcony Chilmark
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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House Balcony Chilmark
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
Details
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House Balcony Chilmark
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

max.
Min.
41°
27°
16 days 16
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39°
25°
15 days 15
max.
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46°
28°
15 days 15
max.
Min.
57°
37°
13 days 13
max.
Min.
66°
48°
13 days 13
max.
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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.
- 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°

70%

2 h

14 mi/h

Mon, 5 Jun
57°
53°

65%

3 h

9 mi/h

Tue, 6 Jun
66°
55°

15%

9 h

12 mi/h

Wed, 7 Jun
62°
55°

15%

3 h

13 mi/h

Thu, 8 Jun
59°
55°

15%

0 h

11 mi/h

Fri, 9 Jun
62°
57°

15%

8 h

9 mi/h

Sat, 10 Jun
64°
57°

10%

9 h

7 mi/h

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:

Booking.com Vacation Rentals in Chilmark TripAdvisor Vacation Rentals in Chilmark Vrbo Vacation Rentals in Chilmark VacationRentals.com Vacation Rentals in Chilmark HouseTrip Vacation Rentals in Chilmark FlipKey Vacation Rentals in Chilmark Homestay.com Vacation Rentals in Chilmark Only-apartments Vacation Rentals in Chilmark Interhome Vacation Rentals in Chilmark Novasol Vacation Rentals in Chilmark HomeEscape Vacation Rentals in Chilmark

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