Vacation Rentals in Osprey Valley Golf, ON: Compare 10+ Sites & Save

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37 Best Vacation Rentals in Osprey Valley Golf (Starting from $76)

Cozy Riverside Cottage in Caledon Alton
Cozy Riverside Cottage in Caledon Alton
House
Alton, Canada
2.4k from Osprey Valley Golf center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
9.0

Fabulous

2 reviews

$271
Average price / night
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Alton Riverside Cottage main floor apartment.
Alton Riverside Cottage main floor apartment.
Apartment
Alton, L7K 0C2, Canada
2.4k from Osprey Valley Golf center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

13 reviews

$463
Average price / night
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Mesmerising Cottage In Caledon
Mesmerising Cottage In Caledon
House
Osprey Valley Golf, Caledon, Ontario, Canada
7.0k from Osprey Valley Golf center

Air Conditioner, Parking, Child Friendly

2 Bedrooms4 Guests
New to Booking
$76
Average price / night
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Exclusive 100-Acre Modern Estate Designed Home
Exclusive 100-Acre Modern Estate Designed Home
House
Alton, L7K 0E2, Canada
2.4k from Osprey Valley Golf center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
New to Booking
$571
Average price / night
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The Perfect Getaway
The Perfect Getaway
House
Orangeville, Canada
7.4k from Osprey Valley Golf center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom6 Guests
New to Booking
$175
Average price / night
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Cozy Country Spring & Summer Getaway | HotTub + Outdoor Pool &  Fire Pits
Cozy Country Spring & Summer Getaway | HotTub + Outdoor Pool & Fire Pits
House
Alton, L7K 0C4, Canada
2.7k from Osprey Valley Golf center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater

3 Bedrooms8 Guests
10.0

Exceptional

14 reviews

$254
Average price / night
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Konia Suites
Konia Suites
House
Orangeville, Canada
8.3k from Osprey Valley Golf center

Security/Safety, Air Conditioner, Internet, Parking, Fireplace/Heating

2 Bedrooms2 Guests
8.2

Very Good

36 reviews

$116
Average price / night
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Newly renovated 1 Bedroom apartment in Alton, Ontario
Newly renovated 1 Bedroom apartment in Alton, Ontario
House
Alton, L7K 1M5, Canada
3.8k from Osprey Valley Golf center

AC, Dryer, Heater, Internet, Laundry, Living Area, No Smoking, Washer

1 Bedroom3 Guests
New to Booking
$208
Average price / night
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Newly Renovated 3BR Orangeville Basement Suite with Private Access, 10 Min Walk to Headwaters Hospital, 5 Min Drive to Mount Alverno Luxury Resorts, Ideal for Medical, Vacation or Work Stays!
Newly Renovated 3BR Orangeville Basement Suite with Private Access, 10 Min Walk to Headwaters Hospital, 5 Min Drive to Mount Alverno Luxury Resorts, Ideal for Medical, Vacation or Work Stays!
Apartment
Orangeville, Canada
8.4k from Osprey Valley Golf center

Apartments, Luxury, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay

3 Bedrooms7 Guests
New to Booking
$193
Average price / night
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Entire private 1 bedroom apartment in Alton ont. A place to relax, pet friendly
Entire private 1 bedroom apartment in Alton ont. A place to relax, pet friendly
House
Alton, L7K 1M5, Canada
3.9k from Osprey Valley Golf center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Patio

1 Bedroom3 Guests
New to Booking
$210
Average price / night
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Comfy & Spacious 4BR Family Home with Free Parking, Laundry & Private Patio! 10 Min Walk to Headwaters Hospital, 5 Min Drive to Mount Alverno Luxury Resorts, Ideal for Medical, Vacation or Work Stays!
Comfy & Spacious 4BR Family Home with Free Parking, Laundry & Private Patio! 10 Min Walk to Headwaters Hospital, 5 Min Drive to Mount Alverno Luxury Resorts, Ideal for Medical, Vacation or Work Stays!
House
Orangeville, Canada
8.4k from Osprey Valley Golf center

Luxury, Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms10 Guests
New to Booking
$214
Average price / night
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Fall Nordic Cottage Retreat with Hot Tub 60 Minutes from City
Fall Nordic Cottage Retreat with Hot Tub 60 Minutes from City
House
Caledon, L7K 1L3, Canada
4.0k from Osprey Valley Golf center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$427
Average price / night
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A rustic cabin in the woods
A rustic cabin in the woods
House
Orangeville, Canada
10.0k from Osprey Valley Golf center

B&bs, Accommodations, Guest houses, Homestays, Cabins, Lodgings, Vacation rentals, Beach, Places to stay

1 Bedroom2 Guests
8.6

Fabulous

5 reviews

$196
Average price / night
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Rustic cabin-inspired residence.\n
Rustic cabin-inspired residence.\n
Cabin
Caledon, L7K 1X9, Canada
4.9k from Osprey Valley Golf center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms10 Guests
9.6

Exceptional

4 reviews

$408
Average price / night
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Perfect 10 acres private quiet property for small events & family gatherings
Perfect 10 acres private quiet property for small events & family gatherings
Cottage
Caledon, L7K 1G3, Canada
6.1k from Osprey Valley Golf center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms14 Guests
New to Booking
$931
Average price / night
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Indoor Heated Pool• Outdoor Hot Tub • Sports Building• 15 acres Woodlands
Indoor Heated Pool• Outdoor Hot Tub • Sports Building• 15 acres Woodlands
House
Erin, N0B 1T0, Canada
6.4k from Osprey Valley Golf center

AC, Balcony, Barbecue, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

4 Bedrooms9 Guests
New to Booking
$832
Average price / night
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PARADISE OVERLOOKING THE  BUBBLING CREDIT RIVER SURRONDED BY LUSH MATURE GARDENS
PARADISE OVERLOOKING THE BUBBLING CREDIT RIVER SURRONDED BY LUSH MATURE GARDENS
House
Belfountain, L7K 0E7, Canada
6.4k from Osprey Valley Golf center

AC, Balcony, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
New to Booking
$156
Average price / night
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Custom-Built 4-Acre Luxury Estate Retreat
Custom-Built 4-Acre Luxury Estate Retreat
House
Caledon Village, L7K 1H4, Canada
6.6k from Osprey Valley Golf center

AC, Balcony, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
New to Booking
$351
Average price / night
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LUXURY EVENT PLACE IN CALEDON.
LUXURY EVENT PLACE IN CALEDON.
Villa
Caledon, L7K 0A5, Canada
7.0k from Osprey Valley Golf center

AC, Balcony, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

3 Bedrooms6 Guests
New to Booking
$3406
Average price / night
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4BR Retreat ~Brand New Detached ~Spotless ~ Erin
4BR Retreat ~Brand New Detached ~Spotless ~ Erin
House
Erin, N0B 1T0, Canada
7.2k from Osprey Valley Golf center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms8 Guests
New to Booking
$282
Average price / night
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Modern Cozy Getaway
Modern Cozy Getaway
House
Orangeville, L9W 4Y3, Canada
7.8k from Osprey Valley Golf center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.2

Superb

5 reviews

$158
Average price / night
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Cozy Basement Apartment (700 sq ft) with Full Kitchen
Cozy Basement Apartment (700 sq ft) with Full Kitchen
Apartment
Orangeville, L9W 4W4, Canada
8.0k from Osprey Valley Golf center

AC, Free Parking, Heater, Internet, Kitchen, No Smoking, TV

1 Bedroom2 Guests
New to Booking
$136
Average price / night
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Cozy One bedroom suite 5min to Orangeville Downtown
Cozy One bedroom suite 5min to Orangeville Downtown
House
Orangeville, L9W 5J4, Canada
8.4k from Osprey Valley Golf center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$145
Average price / night
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Spacious Cozy 4BR Orangeville Home w/Deck! 10-minute walk to Headwaters Hospital
Spacious Cozy 4BR Orangeville Home w/Deck! 10-minute walk to Headwaters Hospital
House
Orangeville, L9W 4W5, Canada
8.5k from Osprey Valley Golf center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
New to Booking
$269
Average price / night
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Romantic Studio Hideaway • Heated Pool Option
Romantic Studio Hideaway • Heated Pool Option
Apartment
Caledon Village, L7K 2B1, Canada
8.7k from Osprey Valley Golf center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom4 Guests
10.0

Exceptional

8 reviews

$183
Average price / night
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Serene Country Oasis • Optional Heated Pool
Serene Country Oasis • Optional Heated Pool
Apartment
Caledon Village, L7K 2B1, Canada
8.7k from Osprey Valley Golf center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms5 Guests
9.6

Exceptional

13 reviews

$212
Average price / night
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Caledon Country Estate 7 day family rental not available for weddings
Caledon Country Estate 7 day family rental not available for weddings
House
Caledon, L7C0E9, Canada
8.8k from Osprey Valley Golf center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

6 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$1936
Average price / night
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Other accommodation types in Osprey Valley Golf:

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Osprey Valley Golf.

Where to stay in Osprey Valley Golf? Best neighborhoods & areas

Osprey Valley Golf Vacation Rentals on the Map

Frequently Asked Questions

You can explore 37 verified vacation rentals in Osprey Valley Golf. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Osprey Valley Golf vary depending on the season, property size, and location. Rates typically start from around $76 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Osprey Valley Golf include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Osprey Valley Golf welcome pets. Currently, 13 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Osprey Valley Golf often include amenities such as Fireplace/Heating, Laundry, and Bedding/Linens. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.