Luxury Homes for Rent in Chilmark, MA (34 Rentals)

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The most luxurious Homes in Chilmark with high-end amenities, features, and finishes.

property at 11 Hammett Ln

$4,250

Total Monthly Price

Total Monthly Price

Base Rent
$4,250

Total Monthly Price
$4,250

2 Bedroom, 2 Bath Home for Rent

Available Now

11 Hammett Ln

ChilmarkMA02535
property at 27 Beach Plum Ln

$7,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,000

Total Monthly Price
$7,000

4 Bedroom, 3.5 Bath Home for Rent

Available Now

27 Beach Plum Ln

ChilmarkMA02535
property at 2 Paddock Cir

$7,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,900

Total Monthly Price
$7,900

3 Bedroom, 2.5 Bath Home for Rent

Available Now

2 Paddock Cir

ChilmarkMA02535
property at 141 N Rd

$10,800

Total Monthly Price

Total Monthly Price

Base Rent
$10,800

Total Monthly Price
$10,800

4 Bedroom, 2 Bath Home for Rent

Available Now

141 N Rd

ChilmarkMA02535
property at 224 N Rd

$13,200

Total Monthly Price

Total Monthly Price

Base Rent
$13,200

Total Monthly Price
$13,200

2 Bedroom, 2 Bath Home for Rent

Available Now

224 N Rd

ChilmarkMA02535
property at 5 Trail End

$16,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$16,000

Total Monthly Price
$16,000

7 Bedroom, 3.5 Bath Home for Rent

Available Now

5 Trail End

ChilmarkMA02535
property at 31 S Ridge Rd

$16,800

Total Monthly Price

Total Monthly Price

Base Rent
$16,800

Total Monthly Price
$16,800

3 Bedroom, 2 Bath Home for Rent

Available Now

31 S Ridge Rd

ChilmarkMA02535
property at 2 Strikers Wy

$22,000

Total Monthly Price

Total Monthly Price

Base Rent
$22,000

Total Monthly Price
$22,000

3 Bedroom, 2.5 Bath Home for Rent

Available Now

2 Strikers Wy

ChilmarkMA02535

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

property at 36 Henry Hough Ln

$22,000

Total Monthly Price

Total Monthly Price

Base Rent
$22,000

Total Monthly Price
$22,000

4 Bedroom, 2 Bath Home for Rent

Available Now

36 Henry Hough Ln

ChilmarkMA02535
property at 44 Flanders Ln

$24,000

Total Monthly Price

Total Monthly Price

Base Rent
$24,000

Total Monthly Price
$24,000

4 Bedroom, 3 Bath Home for Rent

Available Now

44 Flanders Ln

ChilmarkMA02535
property at 56 Chilmark Rd

$24,000

Total Monthly Price

Total Monthly Price

Base Rent
$24,000

Total Monthly Price
$24,000

4 Bedroom, 3.5 Bath Home for Rent

Available Now

56 Chilmark Rd

ChilmarkMA02535
property at 29 Cemetery Rd

$36,000

Total Monthly Price

Total Monthly Price

Base Rent
$36,000

Total Monthly Price
$36,000

3 Bedroom, 3.5 Bath Home for Rent

Available Now

29 Cemetery Rd

ChilmarkMA02535
property at 384 Middle Rd

$40,000

Total Monthly Price

Total Monthly Price

Base Rent
$40,000

Total Monthly Price
$40,000

6 Bedroom, 5 Bath Home for Rent

Available Now

384 Middle Rd

ChilmarkMA02535
property at 19 Lake Rd

$42,000

Total Monthly Price

Total Monthly Price

Base Rent
$42,000

Total Monthly Price
$42,000

5 Bedroom, 2.5 Bath Home for Rent

Available Now

19 Lake Rd

ChilmarkMA02535
property at 6 Trail End

$50,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$50,700

Total Monthly Price
$50,700

4 Bedroom, 3 Bath Home for Rent

Available Now

6 Trail End

ChilmarkMA02535
property at 15 Courtland Dr

$2,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

3 Bedroom, 1.25 Bath Home for Rent

Available Jan 12, 2026

15 Courtland Dr

SandwichMA02537

The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

property at 32 Madison Dr

$2,600

Total Monthly Price

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom, 2 Bath Home for Rent

Available Now

32 Madison Dr

SandwichMA02537
property at 28 Parsons Ln

$3,200

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

5 Bedroom, 3 Bath Home for Rent

Available Now

28 Parsons Ln

FalmouthMA02536
property at 849 State Rd

$3,300

Total Monthly Price

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

3 Bedroom, 2 Bath Home for Rent

Available Now

849 State Rd

AquinnahMA02535
property at 3 Nonquitt Ave

$3,500

Total Monthly Price

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

4 Bedroom, 2 Bath Home for Rent

Available Now

3 Nonquitt Ave

DartmouthMA02748
property at 18 Great Hill Rd

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

4 Bedroom, 2 Bath Home for Rent

Available Now

18 Great Hill Rd

SandwichMA02563
property at 44 Music St

$6,180

Total Monthly Price

Total Monthly Price

Base Rent
$6,180

Total Monthly Price
$6,180

3 Bedroom, 3.5 Bath Home for Rent

Available Now

44 Music St

West TisburyMA02568
property at 227 S Gate Rd

$8,250

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,250

Total Monthly Price
$8,250

7 Bedroom, 5 Bath Home for Rent

Available Now

227 S Gate Rd

West TisburyMA02568
property at 24 Nat's Farm Ln

$10,000

Total Monthly Price

Total Monthly Price

Base Rent
$10,000

Total Monthly Price
$10,000

3 Bedroom, 2 Bath Home for Rent

Available Now

24 Nat's Farm Ln

West TisburyMA02568

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

property at 76 School House Ln

$14,500

Total Monthly Price

Total Monthly Price

Base Rent
$14,500

Total Monthly Price
$14,500

5 Bedroom, 5.5 Bath Home for Rent

Available Now

76 School House Ln

West TisburyMA02568
property at 41 Naushon Rd

$15,000

Total Monthly Price

Total Monthly Price

Base Rent
$15,000

Total Monthly Price
$15,000

5 Bedroom, 6.5 Bath Home for Rent

Available Now

41 Naushon Rd

AquinnahMA02575
property at 19 Lighthouse Rd

$15,000

Total Monthly Price

Total Monthly Price

Base Rent
$15,000

Total Monthly Price
$15,000

3 Bedroom, 2 Bath Home for Rent

Available Now

19 Lighthouse Rd

AquinnahMA02535
property at 50 Carl's Way

$17,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$17,600

Total Monthly Price
$17,600

4 Bedroom, 2 Bath Home for Rent

Available Now

50 Carl's Way

West TisburyMA02568
property at 40 Lighthouse Rd

$18,000

Total Monthly Price

Total Monthly Price

Base Rent
$18,000

Total Monthly Price
$18,000

3 Bedroom, 2.5 Bath Home for Rent

Available Now

40 Lighthouse Rd

AquinnahMA02535
property at 40 Sweet William Way

$19,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$19,000

Total Monthly Price
$19,000

6 Bedroom, 6.5 Bath Home for Rent

Available Now

40 Sweet William Way

West TisburyMA02568
property at 3 E Pasture Ln

$20,000

Total Monthly Price

Total Monthly Price

Base Rent
$20,000

Total Monthly Price
$20,000

4 Bedroom, 4.5 Bath Home for Rent

Available Now

3 E Pasture Ln

AquinnahMA02535
property at 709 Old County Rd

$20,000

Total Monthly Price

Total Monthly Price

Base Rent
$20,000

Total Monthly Price
$20,000

4 Bedroom, 2.5 Bath Home for Rent

Available Now

709 Old County Rd

West TisburyMA02568

Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

property at 836 State Rd

$24,000

Total Monthly Price

Total Monthly Price

Base Rent
$24,000

Total Monthly Price
$24,000

3 Bedroom, 2 Bath Home for Rent

Available Now

836 State Rd

AquinnahMA02535
property at 15 Loon Ln

$34,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$34,000

Total Monthly Price
$34,000

4 Bedroom, 2.5 Bath Home for Rent

Available Now

15 Loon Ln

AquinnahMA02535

Chilmark, MA Local Guide

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

Read Article
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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

Read Article
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Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

decorative image of people with a giant lease agreement

Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Chilmark, MA Rentals by Map

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Frequently Asked Questions about Chilmark

What type of rentals are currently available in Chilmark?

There are currently 45 Apartments for Rent in Chilmark, MA with pricing that ranges from $1,300 to $5,012. There are also 38 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chilmark ranging from $1,385 to $50,700.

What is the current price range for Rental Homes in Chilmark?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Chilmark ranges from $1,385 to $50,700 with an average monthly rent of $16,372.

How much are larger Three and Four Bedroom Rentals in Chilmark?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Chilmark range from $1,890 to $5,012, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $36,000. Four Bedroom Single-Family rentals are also available starting from $1,700 and Four Bedroom Apartments start at $2,245.

Expert Rental Resources

The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.

Articles, How-To's, and Tips

decorative image for Renting with Roommates: Realistic Expectations for Shared Lease article

Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

decorative image for Apartment Common Area Rules: What Renters Need to Know article

Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

decorative image for How to Negotiate Your Apartment Lease and Save Money article

How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

decorative image for The Rental Move-In Inspection Checklist: A Guide for Renters article

The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.