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  3. Chilmark
  4. Menemsha
  5. Rentals by Owner

Discover Your Perfect Menemsha Rentals by Owner

Menemsha Rentals by Owner

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10.0 (1 Review)
House
Hillside Oak
  • Pet Friendly
  • Wheelchair Accessible
  • Balcony/Terrace
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8.6 (5 Reviews)
House
Chilmark Guest House
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
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5.0 (2 Reviews)
House
Beachroad Hideout
  • Security/Safety
  • Sports/Activities
  • Fireplace/Heating
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3.0 (1 Review)
House
Wayside Camp
  • Pet Friendly
  • Balcony/Terrace
  • Security/Safety
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More Top-Rated Rentals by Owner in Menemsha Area

Why Choose Rent By Owner for your Menemsha 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.

Best Times to Visit Menemsha

When should you plan your Rentals by Owner stay?

Timing your visit to this charming coastal area ensures you experience its natural beauty and vibrant community at its best, making it an ideal choice for a memorable vacation in Menemsha, Chilmark.

Peak Season Highlights

summer
Summer (June to August)

During these months, the area is lively with warm weather and bustling activity, making it an ideal time for enjoying the scenic views and vibrant local atmosphere.

Average Temperature Daytime: high 70s to low 80s °F - Nighttime: mid 60s to low 70s °F
autumn
Fall (September to October)

Autumn brings mild temperatures and stunning foliage, encouraging outdoor exploration and a peaceful retreat in this destination's charming surroundings.

Average Temperature Daytime: mid 60s to high 70s °F - Nighttime: mid 50s to mid 60s °F

Off-Season Highlights

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Late Spring (April to May)

In the spring, you can enjoy fewer crowds while experiencing pleasant weather, perfect for exploring the region at a relaxed pace.

Average Temperature Daytime: mid 50s to mid 60s °F - Nighttime: mid 40s to mid 50s °F
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Early Winter (November to December)

During early winter, the area quiets down, offering a serene environment with cooler temperatures that are suitable for a cozy getaway.

Average Temperature Daytime: mid 40s to mid 50s °F - Nighttime: mid 30s to mid 40s °F

Weekly Weather Forecast for Menemsha

How to Book Your Menemsha 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 Menemsha

More Top-Rated Rentals by Owner in Menemsha 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 outdoor dining areas perfect for savoring fresh seafood and local flavors.
  • Relax on private or shared decks that offer scenic views of the surrounding landscape.
  • Take advantage of well-maintained grilling stations for outdoor barbecues with loved ones.
  • Benefit from access to lush gardens or landscaped yards ideal for outdoor gatherings.
  • Make use of spacious patios equipped with seating to unwind after a day exploring the area.
  • Discover outdoor shower facilities to refresh after a day at nearby beaches.
  • Utilize dedicated parking or easy access to outdoor pathways for exploring the region’s natural beauty.

Top Attractions Around Menemsha

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities and scenic views that showcase the natural beauty of Chilmark, making it an ideal destination for relaxing seaside experiences and exploring local coastal attractions.

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Family Activities

  • Menemsha Beach: Enjoy a family day at the picturesque Menemsha Beach, perfect for swimming, picnicking, and watching stunning sunsets along the coastline.
  • Chilmark Community Center: Explore local culture and participate in family-friendly activities and events often hosted at this welcoming regional hub here.
  • Bike Riding Along the Area Trails: Discover scenic trails suitable for all ages, offering wonderful views and a great way to explore the natural beauty of this destination.
  • Fresh Seafood at Local Markets: Savor fresh, locally caught seafood from nearby markets, making for an enjoyable family dining experience in the region.
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Adult Activities

  • Menemsha Sunset Cruises: Experience a captivating evening cruise along the coast, offering stunning views and a relaxing way to enjoy the region's natural beauty.
  • Chilmark Bike Trails: Explore scenic biking routes through the area's charming landscapes, perfect for discovering hidden spots around this coastal region.
  • Local Art Galleries in Menemsha: Visit intimate galleries showcasing regional artwork, providing a cultural experience that complements your stay by the water.
  • Clamming and Shellfishing: Engage in traditional activities here by participating in the region’s renowned clamming practices along the shoreline, ideal for a hands-on outdoor adventure.

Menemsha Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During Sunset Hours: Take advantage of the area's renowned sunset views to enjoy a truly memorable experience right from your rental or local waterfront.
  • Explore Local Markets and Eateries: Discover fresh seafood and regional delicacies at nearby markets, enhancing your authentic taste of this coastal destination.
  • Utilize Water Transport Options: Consider renting a boat or kayak to explore the surrounding waters, offering a unique way to experience the region's maritime charm.
  • Respect the Natural Environment: Follow local guidelines to help preserve the pristine beaches and natural beauty that make your stay here so special.

Transportation Options

  • Private Car Rentals: You can easily rent a private vehicle nearby to explore this charming coastal area at your own pace.
  • Local Taxis and Rideshare Services: Rideshare apps and local taxi services provide convenient transportation options for getting around the region comfortably.
  • Bike Rentals: Biking is a popular way to enjoy the scenic views here, with several rental shops offering bicycles suitable for all levels.
  • Public Transit Options: Limited but available bus services connect this destination to other parts of the island, making it easier to travel without a car.

Local Customs Options

  • Respect for Local Fishing Traditions: Engaging in or observing fishing activities reflects the area's deep-rooted maritime heritage and is appreciated by residents and visitors alike.
  • Celebrating Seasonal Festivals: Participating in seasonal events and festivals offers a meaningful way to connect with the community’s customs and traditions here in this coastal region.
  • Preserving the Environment: Emphasizing eco-friendly practices and respecting protected natural areas helps maintain the region’s scenic beauty and sustainability.
  • Supporting Local Art and Craftsmanship: Appreciating handmade goods and local artisans supports the area's vibrant creative culture and enhances your authentic experience.

Frequently Asked Questions About Menemsha Rentals by Owner

1. What are the top vacation rentals in Menemsha?

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

2. How many Rentbyowner vacation rentals are available in Menemsha?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 95 in the Menemsha 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 Menemsha. 

3. What is the cancellation policy for rental by owner properties in Menemsha, Chilmark?

The cancellation policy varies depending on the individual listing. You should review the specific rental's terms on the listing page or contact the owner directly to understand the rules regarding cancellations and refunds.

4. How do I confirm my reservation for a private rental in this area?

Reservation confirmation typically occurs after you complete the booking process through Rent By Owner. For additional assurance, reach out to the property owner to confirm your reservation details once booked.

5. Are there specific check-in and check-out times I should be aware of when staying at a rental by owner here?

Check-in and check-out times are set by each host and are detailed on the individual listing. It's advisable to review these details before booking or contact the owner for clarification.

6. Is it possible to make special requests or modifications to my stay at a rental in the region?

Many owners accommodate special requests, but it depends on their policies. Contact the property owner directly to discuss any specific needs or modifications before finalizing your booking.

7. What amenities are typically included in rental by owner properties in this destination?

Amenities vary by listing, but common features include kitchens, Wi-Fi, and outdoor spaces. Always review the listing details or ask the owner directly to ensure the property meets your needs.

More Rentals You May Like Near Menemsha

More Top-Rated Rentals by Owner in Menemsha Area