Best Vacation Homes in Grey Highlands
Cottage
10.0(5 Reviews)
2 Bedrooms
1 Bath
8 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
R6,750/Night
7 Nights - R47,254
Bed & Breakfast
9.1(63 Reviews)
7 Bedrooms
6 Baths
14 Guests
157.87 ft²
Oceanfront
Breakfast- Parking
Spa
R2,791/Night
7 Nights - R19,531
R2,806/Night
7 Nights - R19,648
Apartment
9.8(17 Reviews)
1 Bedroom
1 Bath
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
Internet
R2,932/Night
7 Nights - R20,523
House
3 Bedrooms
1 Bath
8 Guests
150.69 ft²
- Oceanfront
Hot Tub- Parking
Ocean View
R8,340/Night
7 Nights - R58,373
New
Cabin
2 Bedrooms
1 Bath
17 Guests
- Hot Tub
Pool- Balcony/Terrace
- Kitchen
R13,444/Night
7 Nights - R94,104
New
Cabin
1 Bedroom
1 Bath
2 Guests
- Spa
- Balcony/Terrace
- Kitchen
- Air Conditioner
R5,201/Night
7 Nights - R36,403
House
2 Bedrooms
1 Bath
8 Guests
- Internet
Child Friendly
Laundry
Bedding/Linens
R5,189/Night
7 Nights - R36,319
Grey Highlands Luxury Rentals
House
16 Bedrooms
14 Baths
16 Guests
- Parking
- Balcony/Terrace
View- Kitchen
R68,520/Night
7 Nights - R479,636
House
10 Bedrooms
7 Baths
12 Guests
- Parking
- Spa
- Balcony/Terrace
- Kitchen
R46,131/Night
7 Nights - R322,920
Hotel
8.8(20 Reviews)
11 Baths
2653.31 ft²
- Balcony/Terrace
- View
- Air Conditioner
- Internet
R38,171/Night
7 Nights - R267,188
House
5 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R19,230/Night
7 Nights - R134,612
Cottage
7 Bedrooms
5 Baths
15 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R17,625/Night
7 Nights - R123,374
New
Cottage
5 Bedrooms
4 Baths
10 Guests
- Hot Tub
- Internet
- Child Friendly
- Laundry
R14,679/Night
7 Nights - R102,750
House
3 Bedrooms
2 Baths
8 Guests
- Kitchen
- Internet
Pet Friendly- Child Friendly
R14,385/Night
7 Nights - R100,698
Ski Chalet
5 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
R13,896/Night
7 Nights - R97,266
Grey Highlands Pet Friendly Vacation Rentals
House
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
R5,138/Night
7 Nights - R35,966
Cottage
1 Bedroom
1 Bath
4 Guests
- Parking
Skiing- Kitchen
- Internet
R4,650/Night
7 Nights - R32,551
Cottage
10.0(142 Reviews)
3 Bedrooms
2 Baths
6 Guests
1800 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
R5,375/Night
7 Nights - R37,631
House
10.0(12 Reviews)
6 Bedrooms
3 Baths
10 Guests
4000 ft²
- Hot Tub
- Parking
- Skiing
- Balcony/Terrace
R12,777/Night
7 Nights - R89,444
Ski Chalet
10.0(11 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Pet Friendly
R6,557/Night
7 Nights - R45,891
House
10.0(8 Reviews)
7 Bedrooms
4 Baths
14 Guests
3200 ft²
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
R11,036/Night
7 Nights - R77,248
House
10.0(4 Reviews)
4 Bedrooms
3 Baths
10 Guests
1750 ft²
Private Pool- Hot Tub
- Parking
- Pool
R9,552/Night
7 Nights - R66,868
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
9 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
R10,118/Night
7 Nights - R70,822
Grey Highlands Large Vacation Homes
Ski Chalet
10.0(4 Reviews)
6 Bedrooms
2 Baths
10 Guests
- Parking
- Spa
- Balcony/Terrace
- Kitchen
R6,950/Night
7 Nights - R48,650
House
10.0(3 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R5,497/Night
7 Nights - R38,489
House
10.0(1 Review)
5 Bedrooms
2 Baths
12 Guests
2600 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
R1,910/Night
7 Nights - R13,374
Cottage
8.6(4 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R6,807/Night
7 Nights - R47,657
House
8.0(2 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
R6,014/Night
7 Nights - R42,106
House
4 Bedrooms
4 Baths
12 Guests
- Hot Tub
- Parking
- Spa
- Skiing
R10,428/Night
7 Nights - R72,992
Ski Chalet
5 Bedrooms
2 Baths
10 Guests
- Internet
- Pet Friendly
- Child Friendly
- Laundry
R9,568/Night
7 Nights - R66,986
House
4 Bedrooms
1 Bath
11 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
R8,646/Night
7 Nights - R60,526
Why Choose Rent By Owner for your Grey Highlands Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Grey Highlands
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here ensures you enjoy ideal weather and local events, making your stay in this region’s vacation rentals truly memorable.
Peak Season Highlights
Summer (June to August)
During the warmest months, this destination experiences its peak season, attracting visitors seeking outdoor activities and scenic views. Booking your vacation rentals early ensures you find the perfect place to enjoy the region's lively summer atmosphere.
Average Temperature Daytime: 25°C - Nighttime: 15°C
Fall (September to October)
As the foliage transforms, many travelers visit to enjoy the breathtaking autumn colors. This off-peak period is ideal for exploring the area's natural beauty and securing a cozy rental at a more affordable rate.
Average Temperature Daytime: 18°C - Nighttime: 8°C
Off-Season Highlights
Early Spring (March to May)
Before the busy summer season begins, the area offers quieter surroundings, making it a peaceful time to rent here and experience the early signs of spring in this destination.
Average Temperature Daytime: 10°C - Nighttime: 2°C
Late Winter (January to February)
These months see fewer visitors as winter sports wind down. It’s a good opportunity to enjoy solitude while booking winter-ready properties in this region, often at reduced rates.
Average Temperature Daytime: -3°C - Nighttime: -12°C
Weekly Weather Forecast for Grey Highlands
How to Book Your Grey Highlands 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 Grey Highlands
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 outdoor dining areas perfect for sunset meals amid the natural beauty of this destination.
- Take advantage of spacious patios or decks ideal for relaxing and entertaining during your stay.
- Make use of private gardens or landscaped yards that offer a peaceful setting in the region.
- Benefit from access to hiking trails or scenic pathways directly from the property for outdoor adventures.
- Relax by a fire pit or outdoor fireplace, perfect for gathering with family and friends amid the area's fresh air.
- Utilize outdoor sports equipment such as badminton or volleyball courts available at select properties.
- Capitalize on screened-in porches or verandas to enjoy the outdoors while staying protected from the elements in this part of Ontario.
Top Attractions Around Grey Highlands
What attractions are nearby?
While staying in this destination, you can explore a variety of outdoor activities such as scenic hiking trails, cycling routes, and tranquil lakeside spots that showcase the natural beauty of the region.
Family Activities
- Blue Mountain Resort: Enjoy a day of family-friendly outdoor activities at this popular ski and recreational area, offering scenic trails and adventure options suitable for all ages.
- Scenic Caves Nature Adventures: Explore underground caves and walk across suspension bridges, providing a thrilling nature experience that the whole family can enjoy here in the region.
- Highland Grounds Farm: Visit this local farm to participate in hands-on activities like fruit picking and animal petting, perfect for creating memorable family moments amidst rural charm.
- Local Arts and Cultural Events: Engage with the vibrant arts scene through seasonal festivals and family-focused workshops that celebrate the community's cultural heritage here in the area.
Adult Activities
- Hiking Trails: Explore scenic hiking routes that wind through the region’s lush forests and picturesque landscapes, offering a peaceful escape into nature.
- Local Art Galleries: Discover unique artworks at galleries showcasing the area's vibrant arts scene and local talent, perfect for cultural enthusiasts.
- Wine Tasting Tours: Enjoy tasting sessions at nearby wineries, where you can sample regional wines amid beautiful vineyard settings.
- Fishing Adventures: Spend a relaxing day casting your line in pristine lakes and rivers known for their excellent fishing opportunities here.
Other Places to Stay in Grey Highlands, ON
Priceville
Kimberley
Old Baldy Conservation Area
South Grey Museum and Historical Library
Artsonten
Eugenia Lake
Feversham
Eugenia Falls Conservation Area
Flesherton
Beaver Valley Ski Club
Markdale
Hoggs Falls
Grey Highlands Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Outdoor Adventures: Take advantage of the region’s natural beauty by exploring local parks and trails to fully immerse yourself in the area's scenic landscapes.
- Book Early for Popular Seasons: Secure your vacation rental during peak times to ensure availability and enjoy the best properties this destination has to offer.
- Check Local Amenities and Services: Choose accommodations that are close to essential services and amenities to make your stay more comfortable and convenient.
- Embrace the Local Charm: Engage with the community and explore local dining options to enrich your experience here beyond just the scenery.
Transportation Options
- Grey Highlands Transit Service: Offers convenient local bus routes that make exploring the area straightforward and accessible for travelers staying in nearby vacation rentals.
- Private Car Rentals: Provides flexible transportation options to help you navigate the region at your own pace and reach more remote attractions comfortably.
- Taxi and Rideshare Services: Available throughout the area, allowing you quick and reliable transportation directly from your accommodation to various destinations.
- Regional Airport Access: The closest airports connect you to major cities, offering easy transfer options for those arriving from afar and planning a seamless journey here.
Local Customs Options
- Traditional Maple Syrup Harvesting: You can witness the region’s time-honored maple syrup tapping, a sweet custom that reflects the area’s rich agricultural heritage.
- Local Craftsmanship and Artisanship: The community values handcrafted goods, giving you the chance to explore artisanal markets and support local creators during your stay.
- Seasonal Outdoor Celebrations: Throughout the year, seasonal festivals and outdoor events celebrate the area's natural beauty and cultural traditions, inviting you to partake in authentic local customs.
- Respect for Indigenous Heritage: The region honors its indigenous roots through respectful practices and community-led initiatives, offering insight into the area’s deep cultural history.
Frequently Asked Questions About Grey Highlands?
1. What are the top vacation rentals in Grey Highlands?
There are a lot of options in Grey Highlands. If you plan on staying in the Grey Highlands area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Grey Highlands:
- Lakefront Spectacle In Beaver Valley/Lake Eugenia
- Secluded Home on Acreage with Scenic Views
- Boho Beaver
- Amazing Bruce Trail hiking near Collingwood, Thornbury
- Sundance of Blantyre Ski Lodge w/Hot Tub & Sauna
- Cottage Paradise - Water, Woods and Nature
- The Castle - 4-bedroom house with AC, WiFi in Grey County
- Malcom Cottage · Stunning 6 Bedroom Chalet In Beaver Valley!
- Charming Beaver Valley Farmhouse - Recently renovated family getaway
- Sweeping Views - Beaver Valley Farmhouse & Pool
2. How many vacation rentals have private pools in Grey Highlands?
There are 1 vacation rentals with private pools near Grey Highlands. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Grey Highlands are best for families?
If you are looking for a family-friendly vacation home in Grey Highlands, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Grey Highlands:
4. How many Rentbyowner vacation rentals are available in Grey Highlands?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 131 in the Grey Highlands 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 Grey Highlands.
5. What is the cancellation policy for vacation rentals in Grey Highlands, Ontario?
Cancellation policies vary by property. It is recommended that you review the specific listing details or contact the property owner directly to understand the terms and any potential fees associated with cancelling your stay here.
6. How do I find out about amenities available at a vacation rental in this region?
Details about amenities are listed on each property’s page. Be sure to read through the listing carefully or reach out to the owner for clarification to ensure the rental meets your needs during your visit.
7. Are there any special requirements or house rules I should be aware of before booking?
Yes, most rentals have specific house rules outlined in the listing. It’s important to review these rules beforehand and contact the owner if you have questions or need additional information about the property here.
8. What is the process for checking in and out of a vacation rental in the area?
Check-in and check-out procedures are detailed in each listing. Some properties offer self-check-in options, while others may require coordination with the owner. Make sure to confirm these details prior to your arrival.
9. Is there a minimum stay requirement for booking a vacation rental in Grey Highlands?
Minimum stay requirements can vary depending on the property. For specific information, please refer to the listing details or contact the owner directly to plan your visit in this part of Ontario.
Grey Highlands Top Rated Vacation Rentals
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
R6,113/Night
7 Nights - R42,796
Bed & Breakfast
9.8(53 Reviews)
1 Bedroom
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
R2,549/Night
7 Nights - R17,848
R2,367/Night
7 Nights - R16,570
House
2 Bedrooms
1 Bath
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R3,930/Night
7 Nights - R27,504
Ski Chalet
10.0(110 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Breakfast
- Parking
- Pool
- Balcony/Terrace
R6,964/Night
7 Nights - R48,751
Other
10.0(3 Reviews)
5 Bedrooms
3 Baths
8 Guests
- Private Pool
- Parking
- Pool
- Kitchen
R5,685/Night
7 Nights - R39,801
Apartment
10.0(3 Reviews)
5 Bedrooms
2 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
R3,366/Night
7 Nights - R23,568
House
9.8(9 Reviews)
7 Bedrooms
8 Baths
16 Guests
3800 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
R16,662/Night
7 Nights - R116,629
