Vineyard Haven Ski Chalets

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9.9 (72 Reviews)
Bed & Breakfast
  • Air Conditioner
  • View
  • Security/Safety
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9.6 (1 Review)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
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9.0 (2 Reviews)
House
  • Air Conditioner
  • View
  • Wheelchair Accessible

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Why Choose Rent By Owner for your Vineyard Haven Ski Chalets?

What makes our Ski Chalets 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 Vineyard Haven

When should you plan your Ski Chalets stay?

Timing your visit here can greatly enhance your experience, as the region offers optimal conditions for enjoying your ski chalets during the winter months when the area is most picturesque and ideal for skiing enthusiasts.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, this destination experiences warm weather ideal for outdoor activities and enjoying the scenic beauty of the region.

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

Autumn offers vibrant foliage and pleasant temperatures, making it a perfect time for exploring and experiencing the area's natural charm.

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

Off-Season Highlights

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Winter (December to February)

This is the quietest season here, with cooler weather that enhances the appeal of cozy stays in winter retreats and ski chalets.

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

Early spring brings mild temperatures and fewer visitors, providing a tranquil setting to enjoy the natural scenery before the busy summer season begins.

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

Weekly Weather Forecast for Vineyard Haven

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.

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

  • You can enjoy a private outdoor patio or deck to relax and take in the scenic surroundings.
  • Many properties offer lush, well-maintained gardens perfect for a peaceful retreat after a day exploring the area.
  • Expect outdoor grilling areas or BBQ facilities to make the most of dining al fresco during your stay.
  • Look for properties with spacious yards ideal for outdoor games or simply enjoying the fresh air.
  • Some rentals feature charming fire pits for cozy evenings under the stars.
  • Ample parking spaces are often available directly on the property, providing convenience during your visit.
  • In warmer months, you might find access to nearby outdoor recreational spaces or walking trails for outdoor enthusiasts.
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Family Activities

  • Manuel F. Correllus State Forest Explore the area's natural beauty through family-friendly hiking and nature walks in this scenic forest reserve.
  • Vineyard Haven Harbor Enjoy a relaxing waterfront experience with boat watching, family picnics, and gentle strolls along the harbor.
  • Island Alpaca Visit this charming farm where your family can learn about alpacas and even participate in interactive tours and feeding sessions.
  • Martha's Vineyard Museum Discover the region’s rich history through engaging exhibits that are perfect for curious young explorers and their families.
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Adult Activities

  • Wine Tasting Tours Indulge in the local flavors by visiting renowned vineyards and wineries, where you can sample exquisite wines amidst picturesque landscapes.
  • Historical Site Visits Explore the rich history of this destination through its well-preserved historical sites, offering insights into the area's unique heritage.
  • Art Galleries and Studios Discover vibrant art scenes with visits to local galleries and artist studios showcasing regional talent and creativity.
  • Harbor Cruises Enjoy scenic harbor cruises that provide stunning views of the coastline and an opportunity to unwind on the water.

Other Places to Stay in Vineyard Haven, MA

Martha's Vineyard
Martha's Vineyard Museum
Island Cove Adventures
Martha's Vineyard Film Center
Martha's Vineyard Chamber of Commerce
Vineyard Playhouse
Island Cove Miniature Golf
Vineyard Haven Public Library

Vineyard Haven Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead: Secure your accommodations early to ensure you have access to the best ski chalets during peak seasons in this popular New England destination.
  • Explore Local Delights: Take time to enjoy regional cuisine and local shops, which offer a genuine taste of the area's welcoming community and vibrant culture.
  • Embrace Outdoor Activities: Make the most of your stay by participating in outdoor pursuits available here, from skiing to scenic winter walks, tailored to the region’s scenic landscape.
  • Utilize Trusted Booking Platforms: Use dependable websites to find trustworthy ski chalets that provide a seamless booking process and excellent customer service for your visit to this destination.

Transportation Options

  • Ferries You can enjoy scenic ferry rides to and from the island, offering a picturesque and convenient way to arrive at this destination.
  • Rental Cars Renting a car provides flexibility and ease in exploring around the region, especially if you're staying in a nearby ski chalet.
  • Public Transit Local bus services operate in the area, making it simple to navigate between accommodations and attractions without the need for a private vehicle.
  • Taxi Services Taxis are readily available for quick and hassle-free transportation within this part of Massachusetts, perfect for spontaneous outings or short trips.

Local Customs Options

  • Local Seafood Traditions: You’ll find that fresh, locally caught seafood is a cornerstone of the area's culinary customs, often celebrated through community events and seasonal festivals.
  • Harbor Etiquette: Respect for maritime practices is essential here, with boaters and visitors alike adhering to specific protocols when engaging with the harbor and fishing fleets.
  • Seasonal Festivals: The region hosts various seasonal festivities that showcase its rich heritage, inviting visitors to participate in local rituals and celebrations.
  • Historical Preservation: Preserving historic buildings and landmarks is a respected tradition, reflecting the community's pride in maintaining its unique cultural identity.

Frequently Asked Questions About Vineyard Haven Rental Ski Chalets

2. How many Ski Chalets are available in Vineyard Haven?

Currently, the total number of properties listed by RBO in 2026 is over 1 in the Vineyard Haven area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Vineyard Haven. 

3. What is the cancellation policy for booking a ski chalet in Vineyard Haven?

The cancellation policy varies by property, so it’s important to read the specific listing details carefully or contact the owner directly to understand the terms and potential fees associated with cancellations.

4. Are there any additional fees I should be aware of when booking a ski chalet in this area?

Additional fees such as cleaning charges, service fees, or local taxes may apply. These details are typically outlined in the listing, but confirming with the property owner ensures you have all the necessary information before booking.

5. What amenities are usually included with a ski chalet in this destination?

Most ski chalets offer amenities like fully equipped kitchens, fireplaces, Wi-Fi, and parking. For specific features, review the individual property listing or reach out to the host for detailed information.

6. How do I ensure my stay complies with local regulations when booking a ski chalet here?

Property owners usually adhere to local regulations, but it’s recommended to check the listing details or contact the owner directly to confirm compliance requirements for your stay.

7. Is there a minimum stay requirement for booking a ski chalet in this region?

Minimum stay requirements can vary depending on the property and season. Details are provided in the listing, or you can contact the owner for clarification on specific booking policies.

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