Discover Your Perfect Monkey Hollow Winery Vacation Homes

Best Vacation Homes in Monkey Hollow Winery

|
7.5 (581 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pool
8.6 (513 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
|
7.6 (255 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
|
6.1 (224 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety

Why Choose Rent By Owner for your Monkey Hollow Winery Vacation Rental Homes?

What makes our Vacation Rentals special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Monkey Hollow Winery

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here can enhance your experience and help you enjoy the region’s unique charm, whether you're seeking a relaxing retreat or an active exploration in this scenic destination.

Peak Season Highlights

spring
Spring (March to May)

During the spring months, the region comes alive with blooming vineyards and pleasant weather, making it an ideal time to enjoy local winery experiences.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
autumn
Fall (September to November)

Autumn offers a vibrant landscape and harvest festivals, providing a perfect backdrop for exploring the area’s scenic winery settings.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

image
Summer (June to August)

While summer brings warm weather, this is also the busier season for the area, so booking ahead ensures you find the best mountain view accommodations.

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

The winter months are quieter, offering a peaceful retreat with cooler temperatures and fewer crowds, ideal for those seeking tranquility in the region.

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

Weekly Weather Forecast for Monkey Hollow Winery

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

  • Enjoy outdoor dining spaces with scenic views of the vineyards and countryside.
  • Relax in a private patio or veranda ideal for unwinding after your day's adventures.
  • Take advantage of well-maintained walking or hiking trails surrounding the area, perfect for exploring nature.
  • Make use of outdoor seating areas designed for socializing or enjoying a peaceful morning coffee.
  • Benefit from outdoor fire pits or outdoor fireplaces to gather with loved ones during cooler evenings.
  • Experience the beauty of lush gardens or landscaped yards that complement the region's natural charm.
  • Access designated picnic areas for a casual meal amidst the serene setting of this destination.
image
image

Family Activities

  • Wine Tasting Tours: Experience family-friendly wine tasting sessions at Monkey Hollow Winery, where you can learn about local vineyards and enjoy scenic views of the surrounding region.
  • Picnic Areas: Take advantage of the winery’s picturesque outdoor spaces to have a relaxing picnic with your loved ones amidst the peaceful countryside.
  • Walking Trails: Explore the well-maintained walking trails on the property that offer an enjoyable way for families to discover the natural beauty of this part of Indiana.
  • Family Events and Festivals: Participate in seasonal family-oriented events hosted at the winery, providing fun activities suitable for all ages during your visit here.
image

Adult Activities

  • Wine Tasting Tours: Embark on guided wine tastings that highlight the region's renowned vintages, offering a refined experience for wine enthusiasts.
  • : Discover the art of winemaking with exclusive tours through the vineyard and cellar, gaining insights into the local viticulture practices.
  • Seasonal Events and Festivals: Participate in special events hosted here throughout the year, celebrating regional traditions and seasonal harvests.
  • Relaxing Vineyard Walks: Enjoy leisurely strolls amid the scenic landscapes of the vineyard, perfect for unwinding and appreciating the area's natural beauty.

Monkey Hollow Winery Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During the Off-Peak Seasons: Opt for visits in the less busy months to enjoy a more relaxed experience and better availability at your preferred vacation rental.
  • Explore Local Wineries and Scenic Spots: Take advantage of the region’s renowned vineyards and picturesque landscapes to enrich your stay here with authentic regional experiences.
  • Book Well in Advance: Secure your preferred vacation rental early to ensure you have the best options available during peak times in this popular destination.
  • Check for Nearby Dining and Entertainment: Identify local eateries and cultural venues close to your rental to make the most of your time here without extensive travel.

Transportation Options

  • Personal Vehicle: Renting or driving your own car offers the most flexibility for exploring the scenic region around Monkey Hollow Winery in Saint Meinrad, Indiana.
  • Taxi and Rideshare Services: Convenient options like local taxis and rideshare apps provide easy access to nearby attractions and amenities in this part of Indiana.
  • Shuttle Services: Some hotels and tour operators in the area offer shuttle services, making it simple to travel between Monkey Hollow Winery and other regional points of interest.
  • Public Transportation: Limited but available bus routes connect the winery area to larger cities and transportation hubs within Indiana, ideal for budget-conscious travelers.

Local Customs Options

  • Respect for Local Heritage: Visitors are encouraged to honor the area's rich history and traditions, which are reflected in the community’s preserved sites and cultural events.
  • Embracing Southern Hospitality: Warm greetings and courteous interactions are a cherished part of the region's welcoming atmosphere that you should embrace during your stay.
  • Participating in Community Events: Engaging in local festivals or gatherings offers a meaningful way to connect with residents and experience authentic regional customs.
  • Environmental Stewardship: The region values sustainable practices, so being mindful of nature and practicing responsible tourism helps preserve its scenic beauty.

Frequently Asked Questions About Monkey Hollow Winery?

2. How many Rentbyowner vacation rentals are available in Monkey Hollow Winery?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 24 in the Monkey Hollow 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 Monkey Hollow Winery. 

3. What is the cancellation policy for booking a vacation rental in this region?

The cancellation policy varies depending on the property owner and listing details. It is recommended to review the specific cancellation terms listed on the property page or contact the host directly for confirmation.

4. How do I inquire about availability and book my stay at a vacation rental here?

Availability can be checked through the listing page, where you can select your preferred dates. To confirm your reservation, follow the booking process outlined or reach out to the host for additional assistance.

5. Are there any house rules or restrictions I should be aware of when staying in these rentals?

Each vacation rental has its own set of house rules and restrictions, which are provided on the listing page. Be sure to read these details carefully before booking and contacting the host if you have any questions.

6. What amenities are typically included in vacation rentals in this destination?

Most properties offer essential amenities such as Wi-Fi, parking, and kitchen facilities. For specific amenities available at a particular rental, please review the listing details or contact the owner directly.

7. Is there a secure way to handle payments and reservations in this area?

Payments are processed securely through the platform hosting the listings. Always confirm your reservation directly through the official booking system to ensure safety and peace of mind.

Best Vacation Homes in Monkey Hollow Winery

9.2 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety
10.0 (1 Review)
House
  • Pet Friendly
  • Balcony/Terrace
  • Sports/Activities