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Chilmark Vacation Rentals

Find 123 available offers from 5 partners
Chilmark
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Farmhouse
Apartment
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+

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.

Show all 123 properties

Best Vacation Home Deals in Chilmark

Save up to 77%

House Chilmark
May 4 - May 11
-52%
$547
$262 per night
House ∙ 3 guests ∙ 2 bedrooms

Nice Vacation Home in Menemsha with Grill & Yard

5.0
Outstanding (57 ratings)
Chilmark, Dukes County, Massachusetts, United States
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House Chilmark
Jun 29 - Jul 6
-18%
$741
$608 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Menemsha with Yard & Grill

4.1
Very good (19 ratings)
Chilmark, Dukes County, Massachusetts, United States
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House Chilmark
Dec 2 - Dec 9
-77%
$965
$224 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Menemsha with Free Parking + 180-Degree View

4.6
Excellent (10 ratings)
Chilmark, Dukes County, Massachusetts, United States
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Find the ideal vacation rental for as little as $200 per night by searching among the 123 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 81%.

Top-Rated Rentals and Accommodations in Chilmark

Book Vacation Rental Offers with the Highest User Rating

House Chilmark
Nov 16 - Nov 23
$266 per night
House ∙ 4 guests ∙ 2 bedrooms

House in Menemsha with Yard & Grill + Pond Views

5.0
Outstanding (36 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

4.7
Excellent (9 ratings)
Chilmark, Dukes County, Massachusetts, United States
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Cottage Chilmark
May 25 - Jun 1
$523 per night
Cottage ∙ 9 guests ∙ 5 bedrooms

Pleasant Cottage in Chilmark with Grill & Yard + Ocean View

5.0
Outstanding (6 ratings)
Chilmark, Dukes County, Massachusetts, United States
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Recommended Vacation Rentals in Chilmark

Find your perfect vacation rental in Chilmark: from $200 per night

House Chilmark
Nov 16 - Nov 23
$715 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Menemsha + Water Views

5.0
Outstanding (18 ratings)
Chilmark, Dukes County, Massachusetts, United States
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House Chilmark
Nov 16 - Nov 23
$535 per night
House ∙ 9 guests ∙ 4 bedrooms

House in Menemsha with Free Parking

5.0
Outstanding (2 ratings)
Chilmark, Dukes County, Massachusetts, United States
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House Chilmark
Dec 2 - Dec 9
$444 per night
House ∙ 10 guests ∙ 4 bedrooms

House in Menemsha with Wood-Burning Fireplace

5.0
Outstanding (11 ratings)
Chilmark, Dukes County, Massachusetts, United States
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House Chilmark
Dec 2 - Dec 9
-47%
$1,071
$570 per night
House ∙ 9 guests ∙ 4 bedrooms

House in Menemsha with Grill & Yard

5.0
Outstanding (6 ratings)
Chilmark, Dukes County, Massachusetts, United States
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House Chilmark
Dec 1 - Dec 8
-34%
$475
$315 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Menemsha with Grill & Yard

4.9
Outstanding (45 ratings)
Chilmark, Dukes County, Massachusetts, United States
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House Chilmark
Dec 1 - Dec 8
-76%
$850
$200 per night
House ∙ 8 guests ∙ 4 bedrooms

Beautiful Vacation Home in Menemsha with Grill + Ocean View

4.5
Excellent
Chilmark, Dukes County, Massachusetts, United States
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Cottage Chilmark
Jun 15 - Jun 22
-20%
$500
$400 per night
Cottage ∙ 5 guests ∙ 2 bedrooms

Rustic Cottage in Menemsha with Grill & Yard + Water Views

5.0
Outstanding (16 ratings)
Chilmark, Dukes County, Massachusetts, United States
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House Chilmark
Dec 2 - Dec 9
-73%
$1,875
$500 per night
House ∙ 10 guests ∙ 5 bedrooms

Beautiful House in Menemsha with Yard & Grill

4.8
Outstanding (18 ratings)
Chilmark, Dukes County, Massachusetts, United States
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House Chilmark
Jul 20 - Jul 27
$940 per night
House ∙ 6 guests ∙ 3 bedrooms

Lovely Vacation Home in Menemsha with Free Parking + Water Views

Chilmark, Dukes County, Massachusetts, United States
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Budget-friendly Vacation Rentals in Chilmark

Find Fantastic yet Inexpensive Offers

House Chilmark
May 25 - Jun 1
-64%
$1,690
$600 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Menemsha with Yard, Grill & Pool

5.0
Outstanding (34 ratings)
Chilmark, Dukes County, Massachusetts, United States
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House Chilmark
Aug 10 - Aug 17
$6,600 per night
House ∙ 10 guests ∙ 4 bedrooms

House in Menemsha with Grill & Yard

5.0
Outstanding (20 ratings)
Chilmark, Dukes County, Massachusetts, United States
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House Chilmark
Dec 23 - Dec 30
$850 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Menemsha with Yard & Grill

Chilmark, Dukes County, Massachusetts, United States
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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  Chilmark
Jul 20 - Jul 27
$929 per night
House ∙ 14 guests ∙ 5 bedrooms

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

4.4
Very good (40 ratings)
Chilmark, Dukes County, Massachusetts, United States
Pet-friendly
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House  Chilmark
Jul 5 - Jul 12
$826 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Menemsha with Grill + Water Views

3.5
Good
Chilmark, Dukes County, Massachusetts, United States
Pet-friendly
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House  Chilmark
Dec 2 - Dec 9
-35%
$1,072
$700 per night
House ∙ 12 guests ∙ 5 bedrooms

Vacation Home in Chilmark with Yard & Grill

5.0
Outstanding (79 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  Chilmark
Dec 2 - Dec 9
$2,000 per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation Home in Menemsha with Yard & Grill

Chilmark, Dukes County, Massachusetts, United States
Balcony
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House  Chilmark
Dec 2 - Dec 9
-35%
$1,000
$650 per night
House ∙ 6 guests ∙ 3 bedrooms

Pleasant House in Chilmark with Grill & Yard + Wonderful Views

5.0
Outstanding (21 ratings)
Chilmark, Dukes County, Massachusetts, United States
Balcony
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House  Chilmark
Feb 3 - Feb 10
$1,350 per night
House ∙ 10 guests ∙ 4 bedrooms

House in Menemsha with Yard & Grill + Water View

5.0
Outstanding (14 ratings)
Chilmark, Dukes County, Massachusetts, United States
Balcony
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Apartments With Balconies or Patios

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

House  Chilmark
Dec 2 - Dec 9
$1,571 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Chilmark with Grill & Yard + Water Views

5.0
Outstanding (14 ratings)
Chilmark, Dukes County, Massachusetts, United States
Balcony/Patio
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House  Chilmark
Nov 16 - Nov 23
$425 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Menemsha with Yard & Grill

4.8
Outstanding (18 ratings)
Chilmark, Dukes County, Massachusetts, United States
Balcony/Patio
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House  Chilmark
May 18 - May 25
-33%
$472
$315 per night
House ∙ 4 guests ∙ 2 bedrooms

House in Menemsha with Grill

5.0
Outstanding (1 rating)
Chilmark, Dukes County, Massachusetts, United States
Balcony/Patio
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Popular Rental Amenities in Chilmark

  • Pet-friendly (49)
  • Air conditioning (103)
  • Pool (7)
  • WiFi (127)
  • TV (105)
  • Fireplace (54)
  • Grill (109)
  • Balcony/patio (4)
  • Washing machine (105)
  • Microwave (104)
  • Parking (2)
  • Kitchen (120)

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 are looking for a pet-friendly rental or you want to stay cool in your vacation home, as most accommodations provide "Pets allowed" and "Air conditioning." It is also possible to find a property in Chilmark if you would like a smoking room as 2 of the listed accommodations there offer "Smoking."

The Weather in Chilmark

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41°
27°
16 days 16
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39°
25°
15 days 15
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46°
28°
15 days 15
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57°
37°
13 days 13
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66°
48°
13 days 13
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73°
55°
11 days 11
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81°
64°
11 days 11
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79°
61°
9 days 9
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75°
54°
9 days 9
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64°
46°
13 days 13
max.
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54°
37°
10 days 10
max.
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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

Wed, 29 Nov
37°
35°

0%

4 h

10 mi/h

Thu, 30 Nov
44°
42°

0%

5 h

10 mi/h

Fri, 1 Dec
53°
51°

15%

0 h

13 mi/h

Sat, 2 Dec
46°
46°

15%

0 h

7 mi/h

Sun, 3 Dec
44°
42°

0%

1 h

14 mi/h

Mon, 4 Dec
48°
46°

15%

0 h

17 mi/h

Tue, 5 Dec
46°
44°

15%

0 h

27 mi/h

Accommodations for your vacation in Chilmark

In Chilmark, most of the 123 accommodation types are house rental, which represent 81.13% of its listed properties. Interestingly, specific accommodation type, this specific type of property is $1,669 a night, with an average area of 194 m². Moreover, if you are going in a group of 8, 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 122 m² on average, with prices averaging $672 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 available 123 homes
💳 Possible discounts up to 81%
🌙 Nightly prices starting at $200
⭐ Popular amenities Pets allowed, Air conditioning and Pool
🐾 Pet friendly homes 49 homes

Frequently Asked Questions

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

The average accommodation in Chilmark is priced at $200 per night. If you would like to stay in a house rental, the average price is $1,669 per night. A cabin Chilmark will cost $672 per night on average.

How many vacation rentals are available to book in Chilmark?

There are 123 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 6 vacation rentals available in Chilmark.

Are dogs allowed in vacation rentals in Chilmark?

Sure, currently there are 49 vacation rentals in Chilmark that allow dogs and the average nightly rate is $2,054.

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.

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