Grey Highlands Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Grey Highlands

Leelas Villa Inn Flesherton
Leelas Villa Inn Flesherton
3 out of 5
774107 Highway 10 South, Grey Highlands, ON
8.2/10 Very Good! (364 reviews)
"Very well maintained and cleaned room. Spacious room and hygienic washroom. This hotel exceeds my expectations. Beautiful hotel within budget. I check-in at 11 PM and staff was available onsite to help me with the process. I’ll definitely recommend anyone looking for the stay."

Reviewed on 6 Jul, 2025

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Leelas Villa Inn Flesherton
Danby House
Danby House
4 out of 5
46 Main Street East, Grey Highlands, ON
The price is S$222 per night from 16 Jul to 17 Jul
S$222
16 Jul - 17 Jul
includes taxes & fees
9.6/10 Exceptional! (137 reviews)
"Friendly and understanding staff. Gorgeous rooms and amenities."

Reviewed on 11 Jul, 2025

Danby House
Pretty River Valley Country Inn
Pretty River Valley Country Inn
4 out of 5
529742 S/R 30-31 Osprey-Blue Mtn. Tline, Grey Highlands, ON
The price is S$269 per night from 14 Jul to 15 Jul
S$269
14 Jul - 15 Jul
includes taxes & fees
9.2/10 Wonderful! (28 reviews)
"Stayed there for one reason only … R&R. It was our second time there and the stay was just what the doctor ordered!"

Reviewed on 28 Apr, 2025

Pretty River Valley Country Inn
See all 1,506 properties in Grey Highlands
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

What to do in Grey Highlands

Collingwood: Blue Mountains Brewery Tour with Tastings

Collingwood: Blue Mountains Brewery Tour with Tastings

S$139
per adult
Collingwood: Blue Mountains Brewery Tour with Tastings
Smartphone Audio Driving Tour between Collingwood and Toronto

Smartphone Audio Driving Tour between Collingwood and Toronto

S$8
per traveller
Smartphone Audio Driving Tour between Collingwood and Toronto
Private Singhampton Caves Hike, Collingwood/Blue Mtn/Creemore

Private Singhampton Caves Hiking Tour, Collingwood/Blue Mountain

S$79
per adult
100% of travellers recommend
Private Singhampton Caves Hiking Tour, Collingwood/Blue Mountain
See all activities in Grey Highlands

Frequently asked questions

How much does a Grey Highlands holiday package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a holiday to Grey Highlands costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Grey Highlands?
If you're hoping to score a cheap Grey Highlands holiday package, consider travelling in January, April and November. You'll usually find lower prices on hotels and flights during these months --- ideal for travellers wishing to save money.
How many days is enough for Grey Highlands?
With a well-organised schedule, you can easily hit the top Grey Highlands sights in a few days. But if you want to discover hidden spots or go on day tours, consider booking your Grey Highlands holiday for longer.
How to find the best Grey Highlands package deals?
Use Expedia's filter tool to find some tempting Grey Highlands package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Grey Highlands package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your holiday package well in advance.
Is it cheaper to book a Grey Highlands holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging stays and flights individually. Better still, you can customise your Grey Highlands trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Grey Highlands?
If you've got your Grey Highlands travel dates finalized, book as early as you can to score some outstanding deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Grey Highlands?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to visit Grey Highlands.
  2. Budget wisely: On top of the cost of your accommodation, you'll need to consider other expenses. These include transportation, flights and food. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Grey Highlands.
  3. Set the duration of your trip: Start by listing all the activities and attractions you'd like to get to in Grey Highlands. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Grey Highlands holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.