Discover Your Perfect Chilmark Vacation Homes

Chilmark Luxury Rentals

See More Chilmark Luxury Vacation Rentals
Find More Chilmark Villas, Resorts, & Rentals on BedroomVillas

Chilmark Pet Friendly Vacation Rentals

|
8.6 (5 Reviews)
House
Chilmark Guest House
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
View Availability
See More Pet-Friendly Vacation Rentals in Chilmark on PetFriendly.io

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

What makes our Vacation Rentals special?

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

Best Times to Visit Chilmark

When should you plan your Vacation Rentals stay?

Choosing the right time to visit this charming destination can enhance your experience, allowing you to enjoy its serene landscapes and coastal beauty at their best, whether you're seeking quiet relaxation or vibrant local events throughout the year.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, this destination experiences its peak season with warm weather and lively outdoor activities. It's an ideal time for beach outings and exploring the region's scenic beauty.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
autumn
Early Fall (September to October)

The early fall offers pleasant weather and vibrant foliage, making it a popular season for those seeking tranquility and scenic views in the area.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F

Off-Season Highlights

image
Late Fall to Early Winter (November to December)

This period sees fewer visitors as the weather cools, providing a more peaceful experience while still enjoying the region’s natural charm.

Average Temperature Daytime: 50°F to 55°F - Nighttime: 40°F to 45°F
image
Winter (January to February)

During winter, the quiet atmosphere is perfect for travelers seeking solitude and cozy retreats in the region’s scenic surroundings.

Average Temperature Daytime: 35°F to 45°F - Nighttime: 25°F to 35°F

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

Outdoor Amenities

  • Enjoy outdoor seating areas perfect for relaxing and dining amid the natural beauty of the region.
  • Take advantage of spacious lawns or gardens ideal for outdoor activities and family gatherings.
  • Benefit from access to private or community swimming pools, offering a refreshing escape during your stay.
  • Explore nearby hiking or walking trails that showcase the scenic landscapes of this coastal destination.
  • Make use of outdoor fireplaces or grills to enhance your culinary experience in the fresh air.
  • Relax in sheltered patios or verandas designed for enjoying sunrise or sunset views over the area's picturesque surroundings.
  • Utilize outdoor showers or hot tubs that provide a luxurious touch to your getaway in this sought-after location.

Top Attractions Around Chilmark

What attractions are nearby?

In this charming destination, you can enjoy a variety of outdoor activities, including pristine beaches, scenic hiking trails, and tranquil nature preserves that showcase the region’s natural beauty.

image
image

Family Activities

  • Chilmark Vineyard Tours: Discover the region’s renowned vineyards and enjoy family-friendly tastings amidst scenic landscapes.
  • Squibnocket Beach: Spend a relaxing day on the sandy shores perfect for swimming, picnicking, and exploring tide pools with your loved ones.
  • Alley’s General Store: Experience a charming local shopping spot where you can pick up essentials and regional treats for your family outing.
  • Martha’s Vineyard Museum: Engage in educational exhibits that highlight the area's rich history, offering an enriching experience for children and adults alike.
image

Adult Activities

  • Chilmark Vineyard Tours: Explore the region’s renowned vineyards and enjoy tasting sessions amidst scenic farm landscapes.
  • Beachcombing at Squibnocket Beach: Spend your days discovering unique shells and enjoying the pristine shoreline of this beloved beach destination.
  • Art Gallery Visits: Appreciate local artistry by browsing through galleries featuring works inspired by the area's natural beauty.
  • Guided Nature Walks: Discover the region's diverse flora and fauna on expertly guided walks through nearby nature preserves.

Other Places to Stay in Chilmark, MA

Dukes County
Dukes County Vacation Rentals
Fulling Mill Brook Preserve
Fulling Mill Brook Preserve Vacation Rentals
The Yard
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 Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local markets and eateries: Take the time to discover the region's unique flavors and artisanal products, enriching your stay in Chilmark by supporting local vendors.
  • Plan outdoor activities carefully: Make the most of the area's natural beauty by scheduling visits to scenic spots early in the day for optimal weather and fewer crowds.
  • Communicate with your hosts: Engage with property owners or managers to gain insider tips and ensure a smooth, enjoyable experience during your visit here.
  • Respect the environment: Practice eco-friendly habits to preserve the scenic landscapes that make this destination so special for future travelers.

Transportation Options

  • Chilmark Ferry Service: Provides scenic and convenient boat trips connecting this part of the region to nearby islands and coastal destinations.
  • Regional Taxi Services: Offers reliable transportation options for exploring the area or traveling to local towns from your vacation rental.
  • Rental Car Agencies: Allows you to explore all around here at your own pace with a variety of vehicles available directly in the region.
  • Public Bus Transit: Serves as an affordable and eco-friendly way to get around, connecting key points within the area and nearby communities.

Local Customs Options

  • Respect for the Land and Nature: Locals hold a deep reverence for the area's natural environment, making sustainable practices and conservation efforts an important part of community life.
  • Seafood and Local Cuisine: Sharing freshly caught seafood is a cherished tradition here, often enjoyed during communal gatherings and local festivals.
  • Traditional Gatherings and Seasonal Events: Participating in seasonal celebrations and community events helps you connect with regional customs and local residents alike.
  • Quiet Respect for Privacy: Maintaining a tranquil ambiance is valued, so visitors are encouraged to keep noise levels considerate, especially in residential areas.

Frequently Asked Questions About Chilmark?

1. 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:

2. 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:

3. How many Rentbyowner vacation rentals are available in Chilmark?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 118 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.