Grey Highlands Vacations from $539

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • Better together

    Save up to $1,045 when you book a flight and hotel together*

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

    Rest easy

    Plan, book, and manage your trip all in one place

Your Grey Highlands Vacation

With one of our vacation packages to Grey Highlands, you'll discover infinite opportunities for fun and relaxation. There's so much to look forward to, including its rural countryside and spectacular views. Fill your free time with tours of Beaver Valley Ski Club, Eugenia Lake and Eugenia Falls Conservation Area, some of the things you simply have to see during your trip to Grey Highlands. Stop daydreaming and start adventuring. Explore the multitude of options on Expedia today and finally put your Grey Highlands vacation plans in motion!

The Latest Grey Highlands vacation packages

Price found within the past 48 hours. Click for updated prices.
Spacious 4-Bedroom Retreat

Spacious 4-Bedroom Retreat

3 out of 5
Save 100% on your flight
Price was $1,026, price is now $539 per person
$539
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
No reviews
New 3BR Townhouse, Minutes to Niagara Falls and Brock University by GLOBALSTAY

New 3BR Townhouse, Minutes to Niagara Falls and Brock University by GLOBALSTAY

4 out of 5
Save 100% on your flight
Price was $1,262, price is now $744 per person
$744
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
8.4/10 Very Good! (21 reviews)
The house its-self was beautiful! Location was convenient. However, I've never stayed in a place that house keeping doesn't check the dishwasher and drier before the next tenant. Showed up at 7pm to a dishwasher full of "clean dishes" that still had food all over them. And their trash was still there. I emailed them to let them know about dishes and trash so I wouldn't get charged. They seemed confused about my complaint. Sure enough when we left we got charged for some of the last tenants garbage.

Reviewed on Aug 25, 2025

12 York by CN tower

12 York by CN tower

2 out of 5
Downtown Toronto
Save 100% on your flight
Price was $2,994, price is now $1,825 per person
$1,825
per person
Dec 22 - Dec 29
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Toronto (YYZ)
10/10 Exceptional! (1 review)
Easy key pickup and convient

Reviewed on Oct 4, 2025

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $1,835, price is now $1,224 per person
$1,224
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Toronto (YYZ)
9.4/10 Exceptional! (595 reviews)
Bed, pillows, linens were excellent. Ne8eds more washroom hooks for towels and clothing.

Reviewed on Oct 4, 2025

Sterling Inn & Spa - an Ontario's Finest Inn

Sterling Inn & Spa - an Ontario's Finest Inn

4 out of 5
Clifton Hill
Price was $806, price is now $562 per person
$562
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Toronto (YYZ)
9.6/10 Exceptional! (2,007 reviews)
Beautiful room, great ambiance, awesome staff, well worth it. the best rooms in Niagara Falls.

Reviewed on Oct 6, 2025

Don't see what you're looking for?
See all available trips from Columbus to Grey Highlands
View all trips

Discover the most popular places to visit in Grey Highlands

Beaver Valley Ski Club

Hit the slopes at Beaver Valley Ski Club during your trip to Grey Highlands. Wander the forest or discover the area's waterfalls.

Beaver Valley Ski Club

Eugenia Falls Conservation Area

Explore the great outdoors at Eugenia Falls Conservation Area, a lovely green space in Flesherton. Wander the forest or discover the area's waterfalls.

Eugenia Falls Conservation Area

Hoggs Falls

Commune with nature and explore the great outdoors at Hoggs Falls during your travels in Flesherton. Wander the forest or discover the area's waterfalls.

Hoggs Falls

What to do in Grey Highlands

Private Singhampton Caves Hike, Collingwood/Blue Mtn/Creemore

Private Singhampton Caves Hiking Tour, Collingwood/Blue Mountain

$62
per adult
100% of travellers recommend
Private Singhampton Caves Hiking Tour, Collingwood/Blue Mountain
Private Nottawasaga Bluffs Caves Hiking Tour,Collingwood/Creemore

Private Nottawasaga Bluffs Caves Hiking Tour,Collingwood/Creemore

$62
per adult
Private Nottawasaga Bluffs Caves Hiking Tour,Collingwood/Creemore
Blue Mountain Private Tour from Toronto

Blue Mountain Private Tour from Toronto

$3,430
per adult
Blue Mountain Private Tour from Toronto
See all activities in Grey Highlands

Grey Highlands Hotel Deals

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
$154 nightly
The price is $174 total per night from Oct 12 to Oct 13
$174 total
Oct 12 - Oct 13
Total with taxes and fees
9.2/10 Wonderful! (32 reviews)
"One of a kind. Great staff. Wonderful location"

Reviewed on Sep 9, 2025

Pretty River Valley Country Inn
Blue Mountain Resort Village Suites

Blue Mountain Resort Village Suites

4 out of 5
156 Jozo Weider Blvd, The Blue Mountains, ON
Fully refundableReserve now, pay when you stay
$162 nightly
The price is $190 total per night from Oct 30 to Oct 31
$190 total
Oct 30 - Oct 31
Total with taxes and fees
8.8/10 Excellent! (4,376 reviews)
"The rooms are quite nice and very close to the mountain."

Reviewed on Oct 2, 2025

Blue Mountain Resort Village Suites
Westin Trillium House, Blue Mountain

Westin Trillium House, Blue Mountain

4 out of 5
220 Gord Canning Drive, The Blue Mountains, ON
Fully refundableReserve now, pay when you stay
$158 nightly
The price is $185 total per night from Nov 2 to Nov 3
$185 total
Nov 2 - Nov 3
Total with taxes and fees
9/10 Wonderful! (1,014 reviews)
"aa"

Reviewed on Oct 1, 2025

Westin Trillium House, Blue Mountain
See all 1,487 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.

Grey Highlands Essential Information

Language
English
Currency
Canadian dollars
Max Temp Winter
25ºF
Max Temp Summer
70ºF
Top Sights
Beaver Valley Ski Club, Hoggs Falls and South Grey Museum and Historical Library

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Grey Highlands vacation package cost?
Offering great value package deals from $539 on Expedia, you'll be surprised at how little a vacation 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?
You can usually find lower rates and better availability in March, April and December. Check out our cheap Grey Highlands vacation packages and you could get some great off-season deals.
How many days is enough for Grey Highlands?
With a well-planned itinerary, you can easily tick off the top Grey Highlands attractions in a handful of days. But if you want to venture off the beaten track or go on day tours, think about booking your Grey Highlands vacation 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 vacation package well in advance.
Is it cheaper to book a Grey Highlands vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging stays and flights individually. Better still, you can customize 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 vacation 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 traveling on a whim.
How to plan a trip to Grey Highlands?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Grey Highlands.
  2. Plan your budget wisely: Besides the cost of your stay, you'll need to consider other expenses. These include transportation, flights and food. Also, set aside some extra funds for unexpected expenses that could crop up during your trip to Grey Highlands.
  3. Explore Grey Highlands using Expedia's trip planning tool: Gain insights into the top attractions and best hotels for your trip to Grey Highlands. You can also save your must-visit places, collaborate with your group and manage your plans in one place.
  4. Decide your trip length: Think about how much time you'd like to spend exploring Grey Highlands. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  5. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick a Grey Highlands vacation package that brings all your bookings together.
  6. Book any activities or day trips: Now to the fun part — locking in everything you want to see and do. Check out some of the best things to do in Grey Highlands, Grey County and reserve your tickets early to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later Grey Highlands vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Grey Highlands break over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.