Discover Your Perfect Chilmark Vacation Homes

Best Vacation Homes in Chilmark

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10.0 (2 Reviews)
House
Bijha's View
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
View Availability
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10.0 (1 Review)
House
Hillside Oak
  • Wheelchair Accessible
  • Balcony/Terrace
  • Accessibility
View Availability
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Chilmark Luxury Rentals

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Chilmark Pet Friendly Vacation Rentals

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Why Choose Rent By Owner for your Chilmark Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Weekly Weather Forecast for Chilmark

How to Book Your Chilmark Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Chilmark

More Top-Rated Vacation Rentals in Chilmark Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Other Places to Stay in Chilmark, MA

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The Yard Vacation Rentals
Menemsha Beach
Menemsha Beach Vacation Rentals
Menemsha Blues Charters
Menemsha Blues Charters Vacation Rentals
Menemsha
Menemsha Vacation Rentals
Waskosim's Rock Reservation
Waskosim's Rock Reservation Vacation Rentals
Chilmark Chocolates
Chilmark Chocolates Vacation Rentals
Lucy Vincent Beach
Lucy Vincent Beach Vacation Rentals
Squibnocket Pond
Squibnocket Pond Vacation Rentals
More Places to Stay Near Chilmark

Chilmark Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Chilmark?

There are a lot of options in Chilmark. If you plan on staying in the Chilmark area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chilmark:

How many vacation rentals have private pools in Chilmark?

There are 1 vacation rentals with private pools near Chilmark. Top-rated RBO homes that have access to a swimming pool include:

Which vacation homes in Chilmark are best for families?

If you are looking for a family-friendly vacation home in Chilmark, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chilmark:

How many Rentbyowner vacation rentals are available in Chilmark?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 125 in the Chilmark area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chilmark.β€―