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Vineyard Haven Luxury Rentals

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Vineyard Haven Pet Friendly Vacation Rentals

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8.3 (12 Reviews)
House
The Lemonade Stand
  • Pet Friendly
  • Wheelchair Accessible
  • Balcony/Terrace
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Vineyard Haven Large Vacation Homes

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6.0 (1 Review)
House
Nana’s Treehouse
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
View Availability
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Why Choose Rent By Owner for your Vineyard Haven 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 Vineyard Haven Vacation Rentals

Where are the best neighborhoods to stay in Vineyard Haven?

When visiting Vineyard Haven, Massachusetts, choosing the right neighborhood to stay in can enhance your overall experience. Located on Martha's Vineyard, Vineyard Haven offers a variety of charming neighborhoods that cater to different preferences, whether you seek proximity to local shops, serene waterfront views, or easy access to ferry terminals. Exploring accommodations in this area allows you to enjoy the authentic coastal atmosphere, with many properties offering comfortable amenities and convenient locations. By selecting a well-situated rental in Vineyard Haven, you ensure a relaxing and memorable stay on Martha’s Vineyard, making it easier to discover everything this picturesque island has to offer.

West Chop

Settled in the scenic region of Vineyard Haven, this area offers peaceful surroundings and charming coastal views, making it an ideal spot for a relaxing getaway. Here, you can enjoy a tranquil environment while exploring the natural beauty that defines this part of the island.

View 612+ Rentals in West Chop

Best Times to Visit Vineyard Haven

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit ensures you experience the best of this destination, with pleasant weather and fewer crowds, making your stay in Vineyard Haven's vacation rentals truly memorable.

Peak Season Highlights

summer
Summer (June to August)

This is the busiest time of year, when the area sees warm weather and lively local activities, making it ideal for enjoying the scenic beauty and maritime charm of this destination.

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

During these months, the region showcases stunning foliage and pleasant temperatures, attracting visitors seeking a picturesque autumn experience and outdoor exploration.

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

Off-Season Highlights

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Spring (April to May)

In spring, the area begins to bloom with mild weather that offers a quieter atmosphere, providing a relaxing setting for those looking to avoid the crowds while exploring nature at its finest.

Average Temperature Daytime: 55-65°F - Nighttime: 40-50°F
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Winter (November to March)

The winter months bring a serene and less crowded environment, perfect for travelers who prefer tranquility and are interested in experiencing the region's peaceful off-season charm.

Average Temperature Daytime: 30-45°F - Nighttime: 20-30°F

Weekly Weather Forecast for Vineyard Haven

How to Book Your Vineyard Haven 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 Vineyard Haven

More Top-Rated Vacation Rentals in Vineyard Haven 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 a private outdoor space with a spacious patio or deck for relaxing and entertaining.
  • Take advantage of lush gardens or landscaped yards that enhance the outdoor ambiance.
  • Make use of outdoor dining areas perfect for savoring meals al fresco during your stay.
  • Relax in a well-maintained backyard with seating arrangements ideal for gatherings under the sun or stars.
  • Utilize outdoor grills or barbecues to prepare delicious meals while enjoying the fresh air.
  • Discover access to nearby outdoor recreation areas, such as parks or walking trails, for outdoor adventures.
  • Benefit from convenient parking facilities in a quiet outdoor setting, enhancing your overall experience here.

Top Attractions Around Vineyard Haven

What attractions are nearby?

In this charming destination, you can enjoy a variety of nearby activities such as exploring scenic beaches, visiting local shops, and immersing yourself in the vibrant community atmosphere that the region offers.

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Family Activities

  • Flying Horses Carousel: Experience a classic family activity at this historic carousel, offering nostalgic fun right in the area.
  • Island Grown Farm Tour: Explore local farms to learn about sustainable agriculture and enjoy fresh, farm-grown produce during your stay.
  • Vineyard Haven Harbor Walk: Stroll along the scenic harbor, watching boats come and go while soaking in the charming coastal atmosphere perfect for all ages.
  • Local Art Galleries & Studios: Discover vibrant regional art within the region's galleries, encouraging creativity and family engagement in this artistic community.
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Adult Activities

  • Wine Tasting Tours: Explore local wineries and indulge in wine tasting experiences that highlight the region's renowned vineyards.
  • Harbor Cruises: Take a scenic boat cruise around the harbor to enjoy stunning views and learn about the area's maritime history.
  • Art Galleries and Studios: Visit diverse art galleries showcasing local talent, offering a vibrant cultural experience in this charming destination.
  • Private Beach Access: Relax at nearby beaches with your own exclusive access, perfect for sunbathing or enjoying a peaceful seaside walk.

Other Places to Stay in Vineyard Haven, MA

Martha's Vineyard
Martha's Vineyard Vacation Rentals
Martha's Vineyard Museum
Martha's Vineyard Museum Vacation Rentals
Island Cove Adventures
Island Cove Adventures Vacation Rentals
Martha's Vineyard Film Center
Martha's Vineyard Film Center Vacation Rentals
Martha's Vineyard Chamber of Commerce
Martha's Vineyard Chamber of Commerce Vacation Rentals
Vineyard Playhouse
Vineyard Playhouse Vacation Rentals
Island Cove Miniature Golf
Island Cove Miniature Golf Vacation Rentals
Vineyard Haven Public Library
Vineyard Haven Public Library Vacation Rentals
West Chop
West Chop Vacation Rentals
Tisbury
Tisbury Vacation Rentals
West Tisbury
West Tisbury Vacation Rentals
Lake Tashmoo
Lake Tashmoo Vacation Rentals
More Places to Stay Near Vineyard Haven

Vineyard Haven Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Markets and Food Scene: Take the time to visit nearby farmers' markets and eateries to experience authentic flavors that showcase the region's culinary culture.
  • Plan Outdoor Activities: Make the most of your stay by engaging in local outdoor pursuits such as walking along scenic waterfronts or exploring lush parks in the area.
  • Discover Unique Art and Craft Shops: Browse through charming shops featuring handmade crafts and artwork that reflect this destination's creative spirit.
  • Enjoy Convenient Access to Transportation: Arrange for transportation options early to easily navigate here and maximize your time exploring all that the region offers.

Transportation Options

  • Ferry Service: Regular ferries connect this area to nearby islands and the mainland, offering a scenic and convenient way to explore the region.
  • Taxi and Rideshare Services: Local taxi companies and rideshare options provide flexible transportation for getting around conveniently within this destination.
  • Car Rentals: Several rental agencies available here allow you to explore the town and surrounding areas at your own pace with ease.
  • Public Transit Buses: Local bus routes serve key points in the region, making it an economical choice for exploring without a vehicle.

Local Customs Options

  • Local Seafood Traditions: You can indulge in the region’s renowned seafood customs, highlighting fresh catches and maritime culinary practices.
  • Harbor Celebrations: Participating in harbor festivals or observing boat parades offers a glimpse into the community’s nautical heritage.
  • Artisan Craftsmanship: Supporting local artisans by exploring craft markets showcases the area’s unique artistic traditions rooted in its coastal culture.
  • Historical Preservation: Respect for historic sites and architecture reflects the region’s commitment to maintaining its rich maritime history.

Frequently Asked Questions About Vineyard Haven?

1. What are the top vacation rentals in Vineyard Haven?

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

2. How many vacation rentals have private pools in Vineyard Haven?

There are 11 vacation rentals with private pools near Vineyard Haven. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Vineyard Haven are best for families?

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

4. How many Rentbyowner vacation rentals are available in Vineyard Haven?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 408 in the Vineyard Haven 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 Vineyard Haven. 

5. What is the cancellation policy for vacation rentals in Vineyard Haven, Massachusetts?

The cancellation policy varies depending on the specific listing you choose. It is important to review the property's cancellation terms directly on the listing page or contact the property owner for detailed information before booking.

6. How do I book a vacation rental in Vineyard Haven, Massachusetts?

You can easily secure your stay by selecting your preferred dates and contacting the property owner through the listing. Be sure to read all details and reach out with any questions to ensure a smooth booking process.

7. Are there any house rules or restrictions I should be aware of in this destination's vacation rentals?

Each property has its own set of house rules and restrictions, which are typically listed on the property page. Reviewing these carefully will help ensure your stay conforms to the owner’s requirements.

8. What amenities are usually included in vacation rentals here?

Amenities vary by property but often include essentials like Wi-Fi, parking, kitchens, and outdoor spaces. Specific amenities are detailed in each listing, so check those before confirming your reservation.

9. Is there a minimum stay requirement for vacation rentals in this area?

Many listings specify a minimum stay requirement, especially during peak seasons. Confirm this detail on the particular property listing or by contacting the owner directly to avoid surprises.

Vineyard Haven Top Rated Vacation Rentals

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