Grey Highlands Holidays

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Grey Highlands Holiday

Our pick of the best Grey Highlands Hotel Deals

Leelas Villa Inn Flesherton

Leelas Villa Inn Flesherton

3 out of 5
774107 Highway 10 South Grey Highlands ON
The price is NZ$150 per night from 14 Nov to 15 Nov
NZ$150
14 Nov - 15 Nov
includes taxes & fees
8.6/10 Excellent! (503 reviews)
"The management was friendly, accommodating, flexible and very pleasant."

Reviewed on 7 Nov 2026

Leelas Villa Inn Flesherton
Danby House

Danby House

4 out of 5
46 Main Street East Grey Highlands ON
Fully refundableReserve now, pay when you stay
The price is NZ$266 per night from 19 Nov to 20 Nov
NZ$266
19 Nov - 20 Nov
includes taxes & fees
9.6/10 Exceptional! (164 reviews)
"Danby House was a great spot for us to stay during our wknd of hiking. The room/bathroom were clean and comfortable. The weather was still nice enough for us to enjoy our balcony in the afternoon sun. Marilynne’s Restaurant is right around the corner and the food was great."

Reviewed on 1 Nov 2026

Danby House
Cottage Paradise - Water, Woods and Nature

Cottage Paradise - Water, Woods and Nature

Flesherton ON
The price is NZ$638 per night from 15 Nov to 16 Nov
NZ$638
15 Nov - 16 Nov
includes taxes & fees
10/10 Exceptional! (6 reviews)
"The pond was lovely, such a nice cabin to spend a few days in. Very friendly and helpful host."

Reviewed on 3 Oct 2026

Cottage Paradise - Water, Woods and Nature
See all 1,552 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.

Stay near popular Grey Highlands attractions

Beaver Valley Ski Club

9.0/10 (17 reviews)
Family-oriented private ski club in Ontario's Grey Highlands with diverse terrain for all skill levels. Members enjoy a tight-knit community with programs for recreational and competitive winter sports enthusiasts.
See properties

What to do in Grey Highlands

Toronto–Collingwood Self-Guided Smartphone Audio Driving Tour

Toronto–Collingwood Self-Guided Smartphone Audio Driving Tour

NZ$11
per traveller
Toronto–Collingwood Self-Guided Smartphone Audio Driving Tour
Blue Mountain Private Tour from Toronto

Blue Mountain Private Tour from Toronto

NZ$5,780
per adult
Blue Mountain Private Tour from Toronto
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.