Discover Your Perfect Martha's Vineyard Vacation Homes

Martha's Vineyard Luxury Rentals

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Martha's Vineyard Pet Friendly Vacation Rentals

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8.6 (6 Reviews)
House
Chilmark Guest House
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
View Availability
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Why Choose Rent By Owner for your Martha's Vineyard 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.

Popular Areas for Martha's Vineyard Vacation Rentals

Where are the best neighborhoods to stay in Martha's Vineyard?

When planning your stay in Martha's Vineyard, Massachusetts, exploring the different neighborhoods can help you find the perfect setting for your getaway. Each area offers its own unique charm and atmosphere, whether you're seeking the vibrant energy of a lively community or the serene tranquility of a quiet retreat. By choosing the right neighborhood, you can enjoy convenient access to local amenities, scenic views, and the distinctive character that makes Martha's Vineyard a popular destination. With a wide selection of vacation rentals available, you'll discover an ideal home base to experience all that this beautiful island has to offer.

Katama

This area offers a peaceful escape filled with charming landscapes and wide-open spaces, perfect for those seeking tranquility on Martha's Vineyard. Here, your vacation rental provides easy access to scenic beaches and outdoor activities in a serene setting.

View 133+ Rentals in Katama

West Chop

Located near the heart of Vineyard Haven, this neighborhood presents a relaxed atmosphere ideal for exploring local shops and waterfront views. Your selection of vacation rentals here promises comfortable convenience in a picturesque and historic part of the region.

View 612+ Rentals in West Chop

Best Times to Visit Martha's Vineyard

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can significantly enhance your experience, as each season offers unique opportunities to enjoy this destination's scenic beauty and relaxed atmosphere.

Peak Season Highlights

summer
Summer (June to August)

During the peak summer months, this island is bustling with visitors enjoying warm weather and vibrant local events, making it an ideal time to explore through comfortable vacation rentals.

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

Early fall offers pleasant weather and fewer crowds, providing a peaceful escape to enjoy the region's natural beauty and cozy accommodations after the busy summer season.

Average Temperature Daytime: 68-75°F - Nighttime: 55-60°F

Off-Season Highlights

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Late Fall and Winter (November to February)

This quieter period features cooler temperatures and fewer visitors, perfect for those seeking serene surroundings and flexible booking options for their vacation rentals.

Average Temperature Daytime: 45-55°F - Nighttime: 35-45°F
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Early Spring (March to May)

As the area begins to awaken from winter, you'll find fewer tourists and more affordable rates on vacation rentals, ideal for experiencing the region's early spring charm.

Average Temperature Daytime: 50-65°F - Nighttime: 40-50°F

Weekly Weather Forecast for Martha's Vineyard

How to Book Your Martha's Vineyard 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 Martha's Vineyard

More Top-Rated Vacation Rentals in Martha's Vineyard 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 dining areas with picnic tables and grills, perfect for al fresco meals amid the scenic surroundings.
  • Relax in a private outdoor pool or hot tub, ideal for unwinding after a day exploring the area's charming towns.
  • Take advantage of beautifully landscaped gardens or lawns that provide tranquil spaces for leisure or outdoor games.
  • Make the most of expansive decks or patios with comfortable seating to soak up the sun and stunning views.
  • Utilize shaded porches or verandas, offering a cool retreat during warm summer days in this coastal region.
  • Explore the area with provided bicycles or outdoor gear for adventures around the town and scenic waterways.
  • Gather around fire pits or outdoor fireplaces for cozy evenings and memorable conversations beneath the stars.

Top Attractions Around Martha's Vineyard

What attractions are nearby?

Within this charming destination, you can enjoy a variety of activities such as exploring scenic beaches, taking leisurely bike rides along picturesque trails, and discovering local art galleries—all just moments from your Martha's Vineyard vacation rentals.

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Family Activities

  • Island Beaches: Spend quality time with your family exploring the pristine beaches that surround this charming destination, perfect for swimming, picnicking, and building sandcastles.
  • Museum of American History: Engage your family's curiosity with interactive exhibits and historical displays that showcase the rich heritage of this region.
  • State Park Adventures: Discover scenic trails and outdoor activities suitable for all ages within the area's lush state parks, ideal for hiking and nature walks.
  • Whale Watching Tours: Experience unforgettable moments by joining family-friendly whale watching excursions that depart from here, providing a close encounter with marine life.
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Adult Activities

  • Wine Tasting Tours: Explore the renowned vineyards and wineries that showcase the region's local wine production, offering a sophisticated experience just minutes from your vacation rental.
  • Art Galleries and Studios: Discover the vibrant arts community with visits to galleries and artist studios that reflect the area's creative spirit and cultural heritage.
  • Cooking Classes: Participate in culinary workshops that highlight regional ingredients and cuisine, perfect for enhancing your stay on this charming island.
  • Adventure Sailing: Embark on a sailing excursion around the coastline, providing panoramic views and an active way to enjoy the area's maritime beauty.

Other Places to Stay in Martha's Vineyard, MA

Dukes County
Dukes County Vacation Rentals
Edgartown
Edgartown Vacation Rentals
Oak Bluffs
Oak Bluffs Vacation Rentals
Vineyard Haven
Vineyard Haven Vacation Rentals
Tisbury
Tisbury Vacation Rentals
Katama
Katama Vacation Rentals
Chilmark
Chilmark Vacation Rentals
West Tisbury
West Tisbury Vacation Rentals
East Chop
East Chop Vacation Rentals
Lagoon Heights
Lagoon Heights Vacation Rentals
Lake Tashmoo
Lake Tashmoo Vacation Rentals
Aquinnah
Aquinnah Vacation Rentals
More Places to Stay Near Martha's Vineyard

Martha's Vineyard Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Seasonal Events: Check the local calendar to align your stay with festivals or outdoor activities that showcase the area's unique charm.
  • Explore Local Dining Options: Sample fresh seafood and regional cuisine at nearby eateries to fully immerse yourself in the region's culinary scene.
  • Discover Scenic Outdoor Spots: Take advantage of the area's natural beauty by visiting beaches and parks that offer picturesque views and relaxing atmospheres.
  • Utilize Local Transportation: Consider renting bikes or using shuttle services to easily navigate around the destination and enjoy its scenic surroundings without hassle.

Transportation Options

  • Car Rentals: Renting a vehicle is a flexible way to explore the island at your own pace, offering easy access to all the scenic spots and local attractions.
  • Ferry Services: The ferry system provides convenient transportation between here and the mainland, making it simple to arrive or depart without the hassle of driving across bridges.
  • Public Buses: The regional bus network offers an economical and eco-friendly option for traveling around the area and reaching key destinations on the island.
  • Taxi and Rideshare Services: Taxis and rideshare options like Uber or Lyft are readily available for quick, hassle-free trips within the region, especially if you prefer not to drive.

Local Customs Options

  • Clambake Tradition: Participating in a traditional clambake is a cherished custom here, offering you a chance to enjoy locally cooked seafood in a social setting.
  • Greeting with a Friendly "Hello": A warm and welcoming greeting is customary when meeting locals, reflecting the area's friendly community spirit.
  • Preserving Maritime Heritage: Respect for the region’s maritime history is evident through local crafts, festivals, and the preservation of historic lighthouse sites.
  • Enjoying the Regional Farmers’ Markets: Visiting farmers’ markets showcases the area's commitment to fresh, local produce, giving you an authentic taste of the region’s agricultural charm.

Frequently Asked Questions About Martha's Vineyard?

1. What are the top vacation rentals in Martha's Vineyard?

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

2. How many vacation rentals have private pools in Martha's Vineyard?

There are 114 vacation rentals with private pools near Martha's Vineyard. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Martha's Vineyard are best for families?

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

4. How many Rentbyowner vacation rentals are available in Martha's Vineyard?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1767 in the Martha's Vineyard 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 Martha's Vineyard. 

5. What is the cancellation policy for vacation rentals in Martha's Vineyard?

Each listing has its own cancellation policy outlined in the terms. To understand your options and potential fees, please review the specific property's cancellation details or contact the owner directly before booking.

6. How do I find available dates and book a rental on this island?

You can check the availability calendar on the listing page and proceed with the booking process. For any questions about dates or special requests, reaching out to the property owner can help ensure your stay aligns with your plans.

7. Are there any house rules or restrictions I should be aware of during my stay?

Yes, each property provides its own set of house rules which are typically listed on the property page. Be sure to read these details carefully and contact the owner if you have specific questions or need clarification.

8. What amenities can I expect in Martha's Vineyard vacation rentals?

Amenities vary by property but generally include essentials like Wi-Fi, kitchen facilities, and outdoor spaces. Detailed descriptions of the amenities are available in each listing, and you can ask the owner about any specific needs.

9. Is there any guidance on check-in and check-out times for rentals on the island?

Check-in and check-out times are specified on each listing. If you require flexible timings, it’s best to communicate directly with the property owner to confirm if arrangements can be made.

Martha's Vineyard Top Rated Vacation Rentals

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