Discover Your Perfect West Chop Vacation Homes

Best Vacation Homes in West Chop

9.8 (87 Reviews)
Hotel
The Attleboro House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
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West Chop Luxury Rentals

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West Chop Pet Friendly Vacation Rentals

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9.0 (1 Review)
House
Brewster House
  • Pet Friendly
  • Wheelchair Accessible
  • Balcony/Terrace
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West Chop Large Vacation Homes

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9.9 (72 Reviews)
Bed & Breakfast
Charles and Charles MV
  • Air Conditioner
  • View
  • Security/Safety
View Availability
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Why Choose Rent By Owner for your West Chop 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.

Best Times to Visit West Chop

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here can enhance your experience, as the region offers different charms and activities depending on the season, making it essential to select a period when the weather and local events align with your vacation plans.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, the area experiences its highest influx of visitors seeking warm weather and outdoor activities. This is the ideal time to enjoy the region's scenic beauty with vibrant local events and bustling beaches.

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

Early fall brings pleasant weather and a colorful landscape, making it a popular choice for travelers looking to avoid the summer crowds while still enjoying mild temperatures and outdoor pursuits.

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

Off-Season Highlights

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Late Fall to Early Winter (November to December)

The region sees a quieter atmosphere during late fall through early winter, offering a peaceful retreat with cooler temperatures and fewer visitors. It’s a great time if you prefer a more relaxed experience.

Average Temperature Daytime: around 45-55°F - Nighttime: 35-45°F
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Winter (January to February)

In the heart of winter, the area becomes less crowded, providing an ideal setting for those seeking tranquility and cozy accommodations. The cooler climate invites indoor relaxation and scenic winter views.

Average Temperature Daytime: around 35-45°F - Nighttime: 20-30°F

Weekly Weather Forecast for West Chop

How to Book Your West Chop 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 West Chop

More Top-Rated Vacation Rentals in West Chop 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 seating areas perfect for relaxing and dining amid scenic views of the region.
  • Take advantage of well-maintained gardens or landscaped yards that add charm to your stay.
  • Make use of spacious decks or patios ideal for entertaining or watching sunsets over the area.
  • Discover access to private or shared outdoor pools for refreshing swims during warm days.
  • Utilize outdoor grilling stations to prepare meals with local ingredients from here or nearby markets.
  • Benefit from outdoor fireplaces or fire pits, perfect for cozy evenings under the stars.
  • Explore the surrounding natural trails or wooded areas directly accessible from your rental property.

Top Attractions Around West Chop

What attractions are nearby?

Here, you can enjoy a variety of outdoor activities and scenic attractions that highlight the natural beauty of the region surrounding West Chop in Vineyard Haven, Massachusetts.

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Family Activities

  • West Chop Lighthouse Tour: Explore this iconic lighthouse to learn about maritime history and enjoy stunning views of the surrounding waters.
  • Farmers Market Visit: Discover local produce and crafts at the vibrant farmers market, perfect for family browsing and tasting regional specialties.
  • Children's Beach Activities: Spend quality time swimming, building sandcastles, or picnicking at a family-friendly beach in the area.
  • Museum of Vineyard Life: Engage with interactive exhibits that showcase the region’s rich history and culture suitable for visitors of all ages.
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Adult Activities

  • Exploring the West Chop Lighthouse: Enjoy a serene walk along the shoreline to admire this historic lighthouse’s scenic views and learn about its maritime significance.
  • Sailing Charter Experiences: Set out on a private sailing adventure to appreciate the coastal beauty and crystal-clear waters of the region.
  • Golfing at Local Courses: Tee off at nearby golf courses offering stunning views and challenging holes, perfect for a leisurely day on the greens.
  • Wine Tasting Tours: Visit local vineyards and enjoy tasting sessions that highlight the region’s unique wine offerings amidst picturesque vineyard settings.

Other Places to Stay in West Chop, MA

West Chop Light
West Chop Light Vacation Rentals
More Places to Stay Near West Chop

West Chop Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Beaches: Take advantage of the scenic beaches nearby to relax, sunbathe, and enjoy water activities that highlight the natural beauty of this coastal region.
  • Visit Quiet Neighborhoods: Stay in charming areas close to your rental to discover the tranquil side of the region and experience authentic local living.
  • Plan Outdoor Activities: Make the most of popular outdoor pursuits such as walking or biking along scenic pathways to immerse yourself in the area's lush landscapes.
  • Experience Local Dining: Savor fresh, regional cuisine at nearby eateries to truly taste the flavors that define this destination's culinary scene.

Transportation Options

  • Ferry Service: The ferry offers scenic, reliable transportation between the area and nearby islands or the mainland, making it a popular choice for visitors seeking a straightforward travel option.
  • Car Rentals: Numerous car rental agencies in this destination provide convenient access to explore the region at your own pace, especially if you prefer flexibility during your stay.
  • Taxis and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available locally, offering a quick and comfortable way to reach your accommodation or explore the surroundings.
  • Bicycle and Pedestrian Paths: Dedicated biking and walking paths allow for eco-friendly, leisurely exploration of the area, perfect for those who enjoy active transportation while savoring the scenery.

Local Customs Options

  • Respect for Maritime Heritage: Locals in the area take pride in their maritime history, often observing local customs that honor sailing traditions and nautical craftsmanship.
  • Community Engagement: Participating in neighborhood events and supporting local artisans is valued, creating a sense of connection among residents and visitors alike.
  • Environmental Respect: Minimizing environmental impact through responsible tourism and adhering to conservation efforts is a common practice here.
  • Celebration of Local Festivals: Engaging in seasonal festivals and community gatherings reflects the region’s rich cultural heritage and friendly spirit.

Frequently Asked Questions About West Chop?

1. What are the top vacation rentals in West Chop?

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

2. How many vacation rentals have private pools in West Chop?

There are 5 vacation rentals with private pools near West Chop. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in West Chop are best for families?

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

4. How many Rentbyowner vacation rentals are available in West Chop?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 597 in the West Chop 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 West Chop. 

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

Cancellation policies vary depending on the property listing. You should review the specific cancellation terms and conditions provided in the rental details or contact the property owner directly for clarification.

6. How do I confirm my reservation at a vacation rental in this destination?

Reservation confirmation typically occurs after completing the booking process and receiving a confirmation email from the listing. For additional assurance, reach out to the property owner if you have any questions about your booking status.

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

House rules and restrictions are listed within each property’s details. It is recommended to read these carefully before confirming your reservation to ensure your plans align with the property’s guidelines.

8. What amenities are generally available in vacation rentals here?

Amenities can vary by property, but most offer essential features such as Wi-Fi, kitchens, and parking. Check the individual listing for a detailed list of amenities included in your chosen rental.

9. Is it possible to make special requests or accommodations when booking a rental in the region?

Special requests can often be discussed directly with the property owner prior to booking. Contact the host through the messaging system to inquire about any specific needs or arrangements.

West Chop Top Rated Vacation Rentals

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