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  3. Chilmark
  4. The Yard
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Discover Your Perfect The Yard Rentals by Owner

The Yard Rentals by Owner

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10.0 (1 Review)
House
Hillside Oak
  • Pet Friendly
  • Wheelchair Accessible
  • Balcony/Terrace
View Availability
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8.6 (5 Reviews)
House
Chilmark Guest House
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
View Availability
More Top-Rated Rentals by Owner in The Yard Area

Why Choose Rent By Owner for your The Yard vacation rental?

What makes our Rentals by Owner 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.

Popular Areas for The Yard Rentals by Owner

Where are the best neighborhoods to stay in The Yard?

When exploring your options for a memorable stay, the neighborhoods around The Yard in Chilmark, Massachusetts, offer a peaceful and scenic retreat. These areas provide a perfect backdrop for those seeking a quiet, private experience while enjoying easy access to the natural beauty of the region. Booking a rental by owner through Rent By Owner ensures you find a comfortable and trustworthy accommodation that complements your trip to this charming part of Massachusetts. Whether you're looking for something secluded or conveniently located near local attractions, these neighborhoods are ideal for a relaxing getaway in Chilmark.

Katama

In this part of the region, you'll find charming vacation rentals that offer a peaceful escape close to natural beauty. It's an ideal spot for those seeking a serene stay with easy access to outdoor activities.

View 131+ Rentals in Katama

West Chop

Here, you can enjoy comfortable rental options in a scenic neighborhood known for its lovely waterfront views and relaxed atmosphere, perfect for unwinding during your visit.

View 829+ Rentals in West Chop

Best Times to Visit The Yard

When should you plan your Rentals by Owner stay?

To make the most of your stay here, consider visiting during the region’s shoulder seasons when you can enjoy pleasant weather and fewer crowds while exploring the area’s natural beauty and tranquil surroundings.

Peak Season Highlights

spring
June to September

During these months, the area experiences its warmest weather, making it ideal for enjoying the outdoors and beaches. This is when you’ll find the region bustling with activity, perfect for those seeking a lively atmosphere.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
spring
Late April to early June

Spring offers pleasant temperatures and vibrant scenery, attracting visitors looking to explore in comfortable weather before the peak summer crowd arrives. It’s an excellent time for serene getaways and outdoor activities.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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October to March

The cooler months bring fewer visitors, providing a quieter experience here. You can enjoy a peaceful retreat while avoiding the summer crowds, with a chance to explore the natural beauty in a more relaxed setting.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F
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Late November to February

Winter offers a tranquil atmosphere with less hustle and bustle. Although temperatures are lower, this season provides a unique opportunity to enjoy the region’s quiet charm and scenic landscapes without the peak-season crowds.

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

Weekly Weather Forecast for The Yard

How to Book Your The Yard vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 The Yard

More Top-Rated Rentals by Owner in The Yard Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 spacious outdoor seating areas perfect for relaxing and entertaining
  • Take advantage of private patios or decks with scenic views of the surrounding landscape
  • Make the most of landscaped gardens and lush lawns for outdoor activities
  • Utilize outdoor grilling stations for convenient barbecues during your stay
  • Relax by a private swimming pool or hot tub, if available in the area
  • Experience outdoor recreation with dedicated walking or hiking trails nearby
  • Benefit from shaded pergolas or covered outdoor spaces ideal for alfresco dining

Top Attractions Around The Yard

What attractions are nearby?

Nearby, you can enjoy a variety of outdoor activities and scenic experiences that highlight the natural beauty of this destination, making your stay both memorable and relaxing.

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Family Activities

  • Chilmark Community Farm: Engage your family in farm activities and enjoy a hands-on experience at this local farm, perfect for kids to learn about sustainable agriculture.
  • Menemsha Beach: Spend a relaxing day by the shore at this scenic beach, ideal for families to swim, explore tide pools, and enjoy stunning sunsets in the area.
  • Alley’s General Store: Explore this historic store where you can pick up local treats and unique souvenirs, offering a charming shopping experience for all ages.
  • Chilmark Preservation Trust Trails: Discover a network of family-friendly walking and biking trails that showcase the region’s natural beauty and provide an active outdoor adventure.
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Adult Activities

  • Beachcombing and Coastal Walks: Enjoy leisurely strolls along the pristine shores, discovering unique shells and marine life typical of this coastal region.
  • Wine Tasting Tours: Explore local vineyards and wineries to sample regional wines that showcase the area's rich agricultural heritage.
  • Bird Watching and Nature Observation: Experience the diverse bird species and native wildlife in natural habitats preserved throughout this destination.
  • Golfing at Scenic Courses: Play a round on world-class golf courses that offer stunning views and a relaxing atmosphere in this tranquil region.

The Yard Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local outdoor activities: Take advantage of the region’s scenic landscapes by engaging in outdoor pursuits such as hiking or biking to truly experience its natural beauty.
  • Connect with nearby communities: Immerse yourself in the area's culture by visiting local markets and engaging with residents for authentic regional experiences.
  • Plan your visit around seasonal events: Check the calendar for seasonal festivals or gatherings that highlight the area's unique charms and traditions.
  • Utilize local transportation options: Make the most of available transit services or car rentals to easily access popular sites and hidden gems within this destination.

Transportation Options

  • Car Rentals: Renting a car is a convenient way to explore the region and access your rental in The Yard, Chilmark, Massachusetts, with numerous local agencies offering flexible options.
  • Public Transportation: The area's public transit system provides reliable bus services that connect you to key destinations within Chilmark and nearby towns.
  • Taxi Services & Rideshares: Taxis and rideshare options like Uber and Lyft are available, offering quick and easy transportation from nearby airports and around the region.
  • Bicycle Rentals: For eco-friendly travel and scenic views, bicycle rentals are a popular choice in the area surrounding your Chilmark vacation rental.

Local Customs Options

  • Respect for the Area's Natural Environment: Locals in this region emphasize sustainable practices and appreciate visitors who are mindful of conserving the area's unique landscape.
  • Community Gatherings and Festivals: Participating in local events fosters a deeper connection with the community and offers insights into traditional customs here.
  • Polite Engagement and Quiet Etiquette: Maintaining a respectful demeanor during interactions and respecting quiet hours is valued by residents and enhances your experience.
  • Preservation of Local Heritage: Visitors are encouraged to honor the region’s history by supporting traditional crafts and adhering to cultural guidelines during their stay.

Frequently Asked Questions About The Yard Rentals by Owner

1. What are the top vacation rentals in The Yard?

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

2. How many Rentbyowner vacation rentals are available in The Yard?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 98 in the The Yard 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 The Yard. 

3. What is the cancellation policy for a rental by owner in this region?

The cancellation policies for rentals vary by owner and listing. You should carefully review the specific terms listed on the property page or contact the owner directly to understand any applicable fees or restrictions before completing your booking.

4. How do I verify the safety and quality of a rental by owner here?

Safety and quality assurances come from detailed listings, host reviews, and property photos provided in the listing. It is recommended to read all guest reviews and reach out to the owner with any questions before finalizing your reservation.

5. Are there any additional fees I should be aware of when booking a rental by owner in this area?

Additional fees such as cleaning charges, security deposits, or service fees may apply depending on the property. These details are typically disclosed in the listing, but it’s best to confirm with the owner directly to avoid surprises during your stay.

6. Is there a minimum stay requirement for rentals in this destination?

Minimum stay requirements differ by property and season. To ensure your plans align, check the specific listing details or contact the owner directly for the most accurate information.

7. How can I communicate with the owner about my booking or special requests?

Communication is typically facilitated through the booking platform’s messaging system. You can reach out to the owner at any time to discuss your questions or special requests before confirming your stay.

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More Top-Rated Rentals by Owner in The Yard Area