Discover Your Perfect Jacob's Vineyard & Winery Vacation Homes

Best Vacation Homes in Jacob's Vineyard & Winery

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

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit this destination ensures you experience its unique charm at its finest, whether you're seeking the lively atmosphere of peak season or the tranquility of quieter months in the region.

Peak Season Highlights

spring
Spring (March to May)

Visit during the spring to enjoy the lush vineyards and vibrant landscapes that start to bloom, making it an ideal time for scenic walks and wine tastings in this region.

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

Experience the stunning fall foliage against the backdrop of the vineyard's harvest season, perfect for outdoor activities and wine tours in this area.

Average Temperature Daytime: 55-70°F - Nighttime: 35-50°F

Off-Season Highlights

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Summer (June to August)

While warm weather makes outdoor activities enjoyable, this period tends to be less crowded, providing a more relaxed visit in the region.

Average Temperature Daytime: 80-90°F - Nighttime: 60-70°F
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Winter (December to February)

During winter, the landscape takes on a quieter, more tranquil ambiance, ideal if you prefer a peaceful retreat away from the peak tourist influx.

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

Weekly Weather Forecast for Jacob's Vineyard & Winery

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

More Top-Rated Vacation Rentals in Jacob's Vineyard & Winery 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 spacious outdoor seating areas perfect for relaxing or dining al fresco amidst the scenic vineyard views.
  • Take advantage of private patios or decks that offer a peaceful spot to unwind while soaking in the fresh regional air.
  • Make use of outdoor grills or barbecues to host delightful cookouts under the Missouri sky.
  • Experience the tranquility of well-maintained walking paths or gardens that showcase the natural beauty of the area.
  • Avail yourself of outdoor fire pits or fireplaces, ideal for evening gatherings and storytelling beneath the stars.
  • Utilize dedicated parking spaces with easy access to your rental, ensuring convenience during your stay here.
  • Take advantage of nearby open spaces or lawns suitable for outdoor activities or leisurely picnics during your visit to this region.

Top Attractions Around Jacob's Vineyard & Winery

What attractions are nearby?

While staying here, you'll find plenty of nearby activities to enjoy in the region, including exploring local wineries and savoring the scenic beauty that makes this destination a perfect spot for relaxation and leisure.

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Family Activities

  • Vineyard & Winery Tours: Discover the art of winemaking with guided tours through the vineyard, perfect for engaging your family in local traditions and rural beauty.
  • Picnic Areas in the Region: Enjoy a family picnic amidst scenic surroundings, making use of designated areas that showcase this area's natural charm and tranquility.
  • Local Nature Trails: Explore nearby hiking and walking trails suitable for all ages, offering outdoor adventures that highlight the region's lush landscape.
  • Seasonal Events & Festivals: Participate in family-friendly festivals or seasonal celebrations hosted here, providing memorable experiences filled with local culture and fun activities.
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Adult Activities

  • Wine Tasting Tours: Experience the region's renowned wines firsthand by participating in guided tastings at Jacob's Vineyard & Winery, where you can savor local flavors crafted from the area's finest grapes.
  • Winery Tours: Discover the winemaking process through informative tours that showcase the vineyard's heritage and craftsmanship right here in this sought-after destination.
  • Relaxing Vineyard Strolls: Enjoy leisurely walks among the scenic vineyards, taking in the natural beauty and tranquility that make this region a perfect retreat for adults seeking relaxation.
  • Exclusive Wine Pairing Events: Attend special events designed for wine enthusiasts, offering expert pairings of local wines with gourmet bites in the picturesque setting of the winery.

Jacob's Vineyard & Winery Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead: Book your stay early to secure the best vacation rentals and enjoy the region’s renowned wine experiences without last-minute stress.
  • Explore Local Wineries: Take advantage of guided tours and tastings at local vineyards to immerse yourself in this destination’s rich viticulture tradition.
  • Discover Scenic Spots: Make time for outdoor excursions around here, where scenic views and peaceful landscapes enhance your overall experience.
  • Enjoy Regional Cuisine: Savor authentic flavors at nearby eateries that showcase the region’s farm-to-table offerings and local specialties.

Transportation Options

  • Personal Vehicles: Having your own car offers the most flexibility for exploring the scenic area surrounding this destination at your own pace.
  • Rental Cars: Several local agencies provide rental vehicles, making it convenient to navigate the region without relying on public transportation.
  • Taxi Services: Taxis are readily available in nearby Kirksville, offering a reliable way to travel to and from Jacob's Vineyard & Winery.
  • Shuttle Services: Private shuttle options operate seasonally, providing a comfortable and direct route between the property and key local attractions in the area.

Local Customs Options

  • Respect for Local Hospitality: In the region, it’s customary to greet hosts with genuine hospitality and appreciation when participating in vineyard tours or tastings.
  • Wine Etiquette: Here, wine tasting involves swirling, sniffing, and savoring each sip thoughtfully, reflecting the area's rich winemaking traditions.
  • Community Celebrations: Attending local festivals or events often includes enjoying regional cuisine and engaging respectfully with residents during community gatherings.
  • Environmental Stewardship: Visitors are encouraged to practice sustainable habits, such as recycling and conserving water, to preserve the scenic beauty of this destination's vineyards and surrounding area.

Frequently Asked Questions About Jacob's Vineyard & Winery?

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 37 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 vacation rentals near Jacob's Vineyard & Winery?

Cancellation policies vary depending on the specific property you choose. It is recommended to review the individual rental listing details or contact the host directly to understand the terms and any potential fees associated with cancellations.

4. How do I secure my booking at a vacation rental in this region?

To reserve your stay, you will typically need to complete the booking through the online platform and may be required to provide a deposit or full payment upfront. Review the listing's booking instructions carefully and reach out to the owner if you have any questions.

5. Are there specific amenities available in vacation rentals close to the winery?

Most properties in this area offer a variety of amenities to enhance your stay, such as Wi-Fi, kitchen facilities, and outdoor spaces. For detailed information, check the individual listing descriptions or contact the property owner directly.

6. What should I know about check-in and check-out procedures for these vacation rentals?

Check-in and check-out times are set by each host and can vary. You’ll find this information in the booking details; for any special requests or questions, it’s best to communicate directly with the property owner prior to your arrival.

7. Is there a minimum stay requirement for booking in this destination?

Minimum stay requirements depend on the property and season. To ensure availability and confirm the length of your reservation, review the listing details or contact the host directly for clarification.

Best Vacation Homes in Jacob's Vineyard & Winery

10.0 (3 Reviews)
Cottage
Base Camp Cottage
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
View Availability
4.1 (48 Reviews)
Hotel
Budget Host Village Inn
  • Air Conditioner
  • Parking
  • Fireplace/Heating
View Availability
9.8 (42 Reviews)
Cottage
Quaint Guest Cottage
  • Air Conditioner
  • Parking
  • Security/Safety
View Availability