Discover Your Perfect Jacob's Vineyard & Winery Rentals by Owner

Jacob's Vineyard & Winery Rentals by Owner

More Top-Rated Rentals by Owner in Jacob's Vineyard & Winery Area

Why Choose Rent By Owner for your Jacob's Vineyard & Winery 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 Jacob's Vineyard & Winery

When should you plan your Rentals by Owner stay?

Choosing the ideal time to visit ensures you can fully enjoy the tranquil beauty and inviting atmosphere of this destination, whether you're seeking a peaceful retreat or an active exploration of the region's offerings.

Peak Season Highlights

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Spring (March to May)

During this time, you can enjoy the blossoming vineyards and lush landscapes that make the region a beautiful destination for wine enthusiasts. This is the period when the area experiences increased visitors seeking to experience the scenic beauty and wine tours.

Average Temperature Daytime: 60-75°F - Nighttime: 40-55°F
autumn
Fall (September to November)

The harvest season attracts many visitors who want to witness the vibrant foliage and participate in grape harvest activities. The region's wineries often host events that appeal to those looking for an authentic tasting experience amidst colorful scenery.

Average Temperature Daytime: 65-70°F - Nighttime: 45-50°F

Off-Season Highlights

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Winter (December to February)

During the colder months, tourism slows down, offering a quieter atmosphere ideal for relaxing stays and enjoying the peaceful vineyard views without the crowds. It is a perfect time for those seeking tranquility and off-season rates.

Average Temperature Daytime: 35-45°F - Nighttime: 20-30°F
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Summer (June to August)

While summer brings warmer weather and longer days, it also sees a dip in tourist activity, making it a serene time to visit while enjoying the warm climate and fewer visitors at local wineries and accommodations.

Average Temperature Daytime: 80-90°F - Nighttime: 60-70°F

Weekly Weather Forecast for Jacob's Vineyard & Winery

How to Book Your Jacob's Vineyard & Winery 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 Jacob's Vineyard & Winery

More Top-Rated Rentals by Owner in Jacob's Vineyard & Winery 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 seating areas where you can relax while taking in the scenic vineyard views.
  • Make the most of private patios or decks perfect for outdoor dining and unwinding after a day of exploring.
  • Take advantage of spacious yards or gardens ideal for outdoor activities or simply soaking up the sunshine.
  • Benefit from on-site parking spaces designed for convenient access to your rental property.
  • Utilize designated barbecue grills for outdoor cooking amidst the peaceful surroundings.
  • Explore nearby walking trails or nature spots that showcase the region's natural beauty.
  • Enjoy yard games or recreational equipment provided to make your outdoor experience more engaging.

Top Attractions Around Jacob's Vineyard & Winery

What attractions are nearby?

While visiting here, you can explore a variety of outdoor activities and local events that showcase the region’s vibrant atmosphere and welcoming community.

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Family Activities

  • Vineyard Tours: Explore the scenic vineyards, where guided tours provide family-friendly insights into local winemaking traditions and the region's agricultural heritage.
  • Picnic Areas: Enjoy relaxing picnics in designated spots surrounded by picturesque views, offering a perfect outdoor activity for families to unwind here in this charming destination.
  • Seasonal Festivals: Participate in seasonal events hosted on the estate, which often feature family-oriented activities and entertainment that celebrate the region's local culture.
  • Farmers Market Visits: Discover fresh produce and handcrafted items at nearby markets, ideal for engaging children in local culinary delights and supporting regional farmers.
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Adult Activities

  • Wine Tasting Tours: Enjoy guided wine tasting experiences at the vineyard, where you can sample local varieties and learn about the winemaking process in this scenic region.
  • Vineyard Walks and Tours: Take a leisurely stroll through the picturesque vineyards to appreciate the lush landscape and gain insights into sustainable farming practices here.
  • Winery Events and Festivals: Participate in seasonal events hosted on-site, offering a chance to connect with fellow enthusiasts and celebrate regional viticulture.
  • Private Tastings and Pairing Sessions: Arrange for exclusive tastings paired with local cheeses or charcuterie, providing an intimate experience amid the beautiful surroundings.

Jacob's Vineyard & Winery Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During the Harvest Season: Scheduling your stay during the harvest time allows you to experience the region's vibrant vineyard atmosphere firsthand.
  • Book a Rental With Scenic Views: Choose accommodations that offer picturesque views of the surrounding vineyards to enhance your relaxing getaway.
  • Explore Local Tasting Rooms: Take advantage of nearby tasting rooms to sample regional wines and deepen your appreciation for the area's winemaking culture.
  • Utilize Local Knowledge from Your Host: Engage with your rental host for insider tips on the best spots around here to fully enjoy your visit to this destination.

Transportation Options

  • Personal Vehicle: Renting or bringing your own car gives you the flexibility to explore this charming region at your own pace, with convenient access to local vineyards and scenic routes.
  • Taxi Services: Reliable taxi options are available here, offering a comfortable and direct way to visit Jacob's Vineyard & Winery without the hassle of parking.
  • Ride-Sharing Apps: Popular ride-sharing services operate in the area, providing an easy and cost-effective transportation solution for visiting local wineries and attractions.
  • Public Transportation: Local bus services connect key points in the region, making it simple to navigate without the need for a personal vehicle while enjoying your stay here.

Local Customs Options

  • Respect for Vineyard Traditions: You’ll find that locals here take pride in preserving the region’s rich winemaking heritage, so participating in or observing traditional grape harvests and wine tastings is highly appreciated.
  • Greeting Etiquette: When visiting farms or local establishments, a friendly nod or verbal greeting is customary, reflecting the welcoming spirit of this close-knit community.
  • Celebrating Local Festivals: Engage in seasonal festivals held in the area to experience authentic regional customs, from harvest celebrations to music events that showcase local talent.
  • Environmental Respect: Visitors are encouraged to follow sustainable practices and respect the natural landscape, which is central to the area's identity and tourism experience.

Frequently Asked Questions About Jacob's Vineyard & Winery Rentals by Owner

1. What are the top vacation rentals in Jacob's Vineyard & Winery?

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

2. How many Rentbyowner vacation rentals are available in Jacob's Vineyard & Winery?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 18 in the Jacob's Vineyard & Winery 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 Jacob's Vineyard & Winery. 

3. What is the cancellation policy for a rental by owner in Jacob's Vineyard & Winery area?

The cancellation terms vary depending on the individual host. Please review the specific cancellation policy listed on the property’s page or contact the owner directly to ensure you understand the conditions before booking.

4. How do I contact the host for inquiries about my stay at a rental in this region?

You can reach out to the property owner through the messaging platform provided on Rent By Owner. It's recommended to clarify all details and any special requests prior to booking to ensure a smooth stay.

5. Are there any additional fees I should be aware of when booking a rental by owner here?

Additional fees such as cleaning, service charges, or local taxes may apply. These fees are typically detailed during the booking process or in the listing description, so be sure to review them carefully.

6. What amenities are typically included in rentals by owner in the local area?

Most rentals offer essential amenities like Wi-Fi, parking, and kitchen facilities. For specific features such as pet policies or outdoor spaces, check the listing details or contact the host directly.

7. Is there a minimum stay requirement for booking a rental in this part of the region?

Minimum stay requirements can vary between properties. Please review the booking details on the listing or contact the owner to confirm any stay length restrictions before proceeding with your reservation.

More Rentals You May Like Near Jacob's Vineyard & Winery

More Top-Rated Rentals by Owner in Jacob's Vineyard & Winery Area