Discover Your Perfect Osprey Valley Golf Vacation Homes

Best Vacation Homes in Osprey Valley Golf

8.2 (36 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety
7.0 (180 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Accessibility

Why Choose Rent By Owner for your Osprey Valley Golf 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 Osprey Valley Golf

When should you plan your Vacation Rentals stay?

Choosing the ideal time to vacation here ensures you can enjoy the region's beautiful landscape and optimal conditions, making your stay both memorable and relaxing.

Peak Season Highlights

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Summer (June to August)

This is the most popular time to visit for golf enthusiasts and those seeking warm weather in the area, making it ideal for enjoying outdoor activities and relaxing stays.

Average Temperature Daytime: 25°C - Nighttime: 15°C
autumn
Early Fall (September to October)

Enjoy the region's stunning autumn foliage and pleasant temperatures as the crowds begin to thin, providing a peaceful retreat while still offering excellent golfing conditions.

Average Temperature Daytime: 20°C - Nighttime: 10°C

Off-Season Highlights

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Late Fall to Winter (November to February)

Experience quieter surroundings and more affordable accommodations as the area transitions into colder weather, ideal for those looking for a serene retreat away from peak crowds.

Average Temperature Daytime: 0°C - Nighttime: -5°C
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Early Spring (March to May)

During this shoulder season, you can enjoy fewer visitors and the gradual warming of the region, perfect for exploring the area's natural beauty and taking advantage of lower rates on vacation rentals.

Average Temperature Daytime: 10°C - Nighttime: 2°C

Weekly Weather Forecast for Osprey Valley Golf

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 a spacious outdoor patio or deck for relaxing and dining al fresco.
  • Take advantage of a private garden or landscaped yard to unwind amidst nature.
  • Make use of outdoor grilling facilities to prepare meals while enjoying the fresh air.
  • Experience the serenity of nearby scenic walking or biking trails within the region.
  • Benefit from access to outdoor swimming pools or hot tubs, perfect for relaxation.
  • Engage in outdoor recreational activities such as tennis or badminton courts available on-site or nearby.
  • Partake in picturesque sunset views or stargazing opportunities in the peaceful surroundings of this destination.
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Family Activities

  • Exploring the Natural Trails: Discover scenic walking and biking paths around the area that are perfect for family outings and enjoying the region's natural beauty.
  • Visit to Local Farms: Engage with the region's agricultural heritage by touring nearby farms, where children can learn about farming practices and perhaps even participate in seasonal activities.
  • Wildlife Watching: Spend quality time observing local wildlife at designated spots, offering educational and memorable experiences for kids and adults alike.
  • Family Golf Activities: Enjoy family-friendly golf sessions designed for all skill levels, providing fun and relaxation amid the lush landscapes of this destination.
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Adult Activities

  • Golfing on the Championship Courses: Enjoy a round of world-class golf at Osprey Valley Golf, where the scenic views and challenging layouts offer an exceptional experience for golf enthusiasts visiting this region.
  • Spa and Wellness Treatments: Indulge in relaxing spa services available nearby to unwind after a day on the links, enhancing your stay in this charming destination.
  • Exploring Local Trails: Discover the natural beauty of the area's parks and trails, perfect for walking or cycling, providing a peaceful retreat amidst lush surroundings.
  • Dining at Local Eateries: Savor delicious regional cuisine at nearby restaurants that showcase the culinary delights of this part of Ontario, ideal for memorable dining experiences during your visit.

Osprey Valley Golf Travel Tips

How Can You Make the Most of Your Stay?

  • Book Early for Popular Dates: Secure your preferred stay well in advance to enjoy the best accommodations during peak golf and local events in the area.
  • Explore Local Dining Options: Take advantage of nearby restaurants and cafes to experience the region's culinary delights without straying too far from your rental.
  • Plan Your Golf Days: Schedule tee times ahead of your arrival to ensure you can enjoy the acclaimed courses here without last-minute hassles.
  • Utilize On-Site Amenities: Make the most of the on-site facilities and recreational options to enhance your stay in this scenic destination.

Transportation Options

  • Private Car Services: Conveniently explore the region with local car rental agencies that offer flexible transportation options around Osprey Valley Golf and nearby Caledon.
  • Taxi and Rideshare Services: Reliable taxi companies and rideshare apps provide quick and easy transportation for visitors looking to travel within the area seamlessly.
  • Public Transit: The area's public transit system offers an economical way to access key spots around Caledon and connect to larger transportation networks.
  • Bicycle Rentals: For a more active experience, bike rentals are available here, allowing you to enjoy the scenic surroundings of the region at your own pace.

Local Customs Options

  • Respect for Golf Course Etiquette: In this region, maintaining quiet and showing courtesy on the golf course is highly valued to ensure an enjoyable experience for all players.
  • Celebration of Local Agriculture: Visitors often participate in seasonal farm activities and enjoy local produce, reflecting the area's rich agricultural heritage.
  • Appreciation for Nature and Conservation: It’s customary to follow environmentally conscious practices, including respecting wildlife and preserving the natural beauty of the surroundings.
  • Politeness and Hospitality: Warm and friendly interactions with locals are appreciated, embodying the welcoming spirit of this destination.

Frequently Asked Questions About Osprey Valley Golf?

2. How many Rentbyowner vacation rentals are available in Osprey Valley Golf?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 67 in the Osprey Valley Golf 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 Osprey Valley Golf. 

3. What is the cancellation policy for vacation rentals near Osprey Valley Golf in Caledon?

The cancellation policy varies depending on the specific property you choose. To ensure you understand the terms, please review the cancellation details listed on the property page or contact the property owner directly.

4. How do I find available dates and book a vacation rental close to Osprey Valley Golf?

You can easily check availability by selecting your preferred travel dates on the listing page. Once you've found a suitable rental, follow the booking process to secure your stay here.

5. Are pets allowed in vacation rentals near this destination?

Pet policies differ between properties. Be sure to read the pet policy details provided in the listing or reach out to the host to confirm if your furry friend can join your stay.

6. What amenities are typically included in vacation rentals around Caledon?

Most vacation rentals offer essential amenities such as Wi-Fi, parking, and fully equipped kitchens. For specific features, refer to the property's listing details or contact the owner for clarification.

7. What should I do if I need to cancel my reservation for a vacation rental in the area?

If you need to cancel, review the property's cancellation policy and contact the host directly to discuss your options. It's recommended to do this as early as possible to avoid any penalties or fees.

Best Vacation Homes in Osprey Valley Golf

9.4 (3 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
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8.2 (251 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Bedding/Linens
  • Wellness Facilities
6.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly