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Discover Your Perfect Chilmark Cabin Rentals

Chilmark Cabin Rentals

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10.0 (1 Review)
House
Hillside Oak
  • Pet Friendly
  • Wheelchair Accessible
  • Balcony/Terrace
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8.6 (6 Reviews)
House
Chilmark Guest House
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
View Availability
10.0 (5 Reviews)
Cottage
Bright and cozy menemsha cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
More Top-Rated Cabin Rentals in Chilmark Area

Why Choose Rent By Owner for your Chilmark Cabin Rentals?

What makes our Cabin 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.

Best Times to Visit Chilmark

When should you plan your Cabin Rentals stay?

To make the most of your stay here, consider visiting during the shoulder seasons when the area offers a quieter atmosphere and more favorable weather for enjoying your chosen cabins in Chilmark, Massachusetts.

Peak Season Highlights

summer
Summer (June to August)

This is the most popular time to visit, with warm weather ideal for exploring the area's scenic beauty and outdoor activities. Seasonal events and long daylight hours make it a lively period for your stay.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 65°F
autumn
Fall (September to November)

During this time, the region transforms with vibrant foliage, attracting visitors seeking a picturesque retreat. The pleasant temperatures and fewer crowds create an excellent setting for relaxing in your cozy cabin.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 55°F

Off-Season Highlights

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Winter (December to February)

Visit during the colder months for a peaceful experience away from the busy season. Though cooler, the area offers tranquility perfect for a quiet retreat in your rented cabin.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
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Spring (March to May)

In early spring, the region begins to bloom, and the weather gradually warms, making it suitable for visitors interested in a more subdued and serene getaway. Fewer tourists mean more privacy for your stay.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 40°F to 45°F

Weekly Weather Forecast for Chilmark

How to Book Your Chilmark Cabin Rentals

What's our booking process?

Our platform allows you to browse a curated selection of cabin 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 Cabin Rentals in Chilmark Area

Common Cabin Rentals Amenities

What amenities can you expect?

Our Cabin 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 a spacious outdoor patio or deck perfect for relaxing after exploring the area.
  • Take advantage of private gardens or landscaped yards to immerse yourself in the natural surroundings.
  • Make the most of outdoor dining areas, ideal for enjoying meals with scenic views.
  • Utilize outdoor grilling stations or barbecues for flavorful cooks during your stay.
  • Relax on hammocks or lounge chairs nestled in lush green spaces.
  • Benefit from access to shared or private outdoor pools for cooling off on warm days.
  • Explore nearby walking trails or outdoor recreational spaces just steps from your accommodations.

Top Attractions Around Chilmark

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities such as scenic hiking, bird watching, and exploring local beaches, offering a perfect blend of relaxation and adventure for your stay in Chilmark, Massachusetts.

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Family Activities

  • Chilmark Vineyard Tour: Explore local vineyards that offer family-friendly experiences and scenic views, perfect for a relaxing day in this charming region.
  • Menemsha Beach: Spend quality time with your loved ones at this picturesque beach, ideal for picnics, swimming, and enjoying breathtaking sunsets.
  • Farmers Market: Visit the area’s farmers market to discover fresh produce and artisan goods, great for family outings and supporting local vendors.
  • Public Nature Trails: Discover the region’s outdoor trails that are suitable for families seeking memorable nature walks and birdwatching adventures.
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Adult Activities

  • Chilmark Vineyard Tours: Explore the area's renowned vineyards, where you can enjoy wine tastings amidst stunning scenic views, making it a perfect activity for relaxation and appreciation of local craftsmanship.
  • Beach Relaxation at Lucy Vincent Beach: Spend your days unwinding on this pristine beach known for its soft sands and clear waters, ideal for sunbathing or peaceful strolls just steps from your cabin.
  • Explore the Menemsha Harbor: Visit this charming harbor to experience the authentic maritime atmosphere, watch local fishermen at work, or indulge in fresh seafood from nearby vendors.
  • Birdwatching and Nature Walks: Engage with the region’s rich natural habitats through guided walks or solo adventures, perfect for connecting with the area's diverse birdlife and lush landscapes.

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Chilmark Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Peak Seasons: Book your cabins well in advance to secure the best options and enjoy a stress-free stay during popular times of the year.
  • Explore Local Dining Options: Take advantage of the area’s unique culinary offerings by visiting local eateries, enhancing your overall experience here.
  • Discover Natural Beauty: Use your accommodation as a base to explore the region’s scenic landscapes and serene beaches, making the most of this destination’s outdoor appeal.
  • Connect with the Community: Engage with local events and activities to gain an authentic perspective of the area and enrich your visit to this charming region.

Transportation Options

  • Car Rental Services: Renting a car here offers the flexibility to explore Chilmark and its scenic surroundings at your own pace, making it a popular choice among visitors seeking convenience and independence.
  • Public Transportation: The regional bus services connect key points within the area, providing an affordable and eco-friendly way to navigate without the need for a private vehicle.
  • Taxi and Ride-Sharing: Taxis and ride-sharing options are readily available, offering quick and reliable transportation for short trips or airport transfers in this destination.
  • Biking and Walking: With charming paths and scenic landscapes, biking and walking are excellent ways to enjoy the area's quiet beauty while reaching nearby amenities comfortably.

Local Customs Options

  • Respect for the Local Fishing Traditions: Engaging in sustainable fishing practices and honoring the area's fishing heritage is highly valued by residents here.
  • Celebration of Harvest Festivals: Participating in seasonal harvest festivals reflects the community’s appreciation for local agriculture and regional produce.
  • Preservation of Historic Lighthouses: Maintaining and respecting the historic lighthouses along the coast demonstrates a deep respect for maritime history.
  • Embracing Outdoor Skills and Sports: Practicing outdoor activities like kayaking or hiking aligns with the region’s outdoor lifestyle and respect for nature.

Frequently Asked Questions About Chilmark Rental Cabins

1. What are the top Cabins 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 Cabins in Chilmark:

2. How many Cabins are available in Chilmark?

Currently, the total number of properties listed by RBO in 2026 is over 118 in the Chilmark area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cabins in Chilmark. 

3. What is the cancellation policy for cabins in this area?

Cancellation policies vary depending on the host and specific listing. To ensure you understand the terms, please review the cancellation details provided on the listing or contact the property owner directly before booking.

4. Are pets allowed in the cabins near here?

Pet policies are determined by individual hosts, so it's important to check the specific listing for any restrictions or pet fees. You can find this information in the property description or reach out to the owner for clarification.

5. Is there a minimum stay requirement when booking here?

Minimum stay requirements depend on the season and the host’s preferences. Details about length of stay are listed on each property page, or you can inquire directly with the owner for more information.

6. Are linens and kitchen amenities included with the cabins?

Most listings offer linens and essential kitchen supplies, but it’s best to confirm this directly on the property listing or by contacting the host to ensure all your needs are met during your stay.

7. How do I verify the availability of cabins in this region?

Availability calendars are updated regularly on the listing pages. For real-time availability and to secure your reservation, it’s recommended to book directly through the listing or communicate with the property owner.

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