Cheap Vacations in Grey Highlands

Choose two or more items and save on your trip:

3-night Grey Highlands vacations

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Toronto Downtown Centre by IHG

Holiday Inn Toronto Downtown Centre by IHG

3.5 out of 5
Price was $790, price is now $613 per person
$613
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
Modern Downtown Apartments

Modern Downtown Apartments

4 out of 5
Price was $943, price is now $641 per person
$641
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Price was $1,879, price is now $1,291 per person
$1,291
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
Town Inn Suites Hotel

Town Inn Suites Hotel

3.5 out of 5
Price was $873, price is now $625 per person
$625
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
Elegant Downtown Apartments

Elegant Downtown Apartments

4 out of 5
Price was $911, price is now $653 per person
$653
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
Teahouse Condos in Downtown Toronto

Teahouse Condos in Downtown Toronto

4 out of 5
Price was $932, price is now $675 per person
$675
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
Revery Toronto Downtown, Curio Collection by Hilton

Revery Toronto Downtown, Curio Collection by Hilton

4 out of 5
Price was $989, price is now $724 per person
$724
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
Holiday Inn Express Toronto - Downtown by IHG

Holiday Inn Express Toronto - Downtown by IHG

3 out of 5
Price was $919, price is now $694 per person
$694
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
TOOR Hotel Toronto, part of JdV by Hyatt

TOOR Hotel Toronto, part of JdV by Hyatt

4 out of 5
Price was $962, price is now $731 per person
$731
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
Yonge Street Downtown Toronto Condos

Yonge Street Downtown Toronto Condos

4 out of 5
Price was $947, price is now $726 per person
$726
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
Park Hyatt Toronto

Park Hyatt Toronto

5 out of 5
Price was $1,541, price is now $1,190 per person
$1,190
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
Canopy By Hilton Toronto Yorkville

Canopy By Hilton Toronto Yorkville

4.5 out of 5
Price was $803, price is now $626 per person
$626
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)

4-night Grey Highlands vacations

Price found within the past 48 hours. Click for updated prices.
Pickering Casino Resort Hotel

Pickering Casino Resort Hotel

4 out of 5
Price was $659, price is now $506 per person
$506
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
Price was $1,690, price is now $997 per person
$997
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
One King West Hotel & Residence

One King West Hotel & Residence

4 out of 5
Price was $1,129, price is now $780 per person
$780
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
Revery Toronto Downtown, Curio Collection by Hilton

Revery Toronto Downtown, Curio Collection by Hilton

4 out of 5
Price was $1,258, price is now $889 per person
$889
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
Town Inn Suites Hotel

Town Inn Suites Hotel

3.5 out of 5
Price was $946, price is now $675 per person
$675
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
TOOR Hotel Toronto, part of JdV by Hyatt

TOOR Hotel Toronto, part of JdV by Hyatt

4 out of 5
Price was $1,077, price is now $788 per person
$788
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
Kent Motel Niagara on the Lake

Kent Motel Niagara on the Lake

2.5 out of 5
Price was $802, price is now $587 per person
$587
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
Canopy By Hilton Toronto Yorkville

Canopy By Hilton Toronto Yorkville

4.5 out of 5
Price was $971, price is now $734 per person
$734
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
South Landing Inn Niagara on the Lake

South Landing Inn Niagara on the Lake

3.5 out of 5
Price was $916, price is now $697 per person
$697
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
Vittoria Hotel and Suites

Vittoria Hotel and Suites

3.5 out of 5
Price was $747, price is now $570 per person
$570
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
Waterfront Hotel Downtown Burlington

Waterfront Hotel Downtown Burlington

3 out of 5
Price was $662, price is now $512 per person
$512
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
Elegant Downtown Apartments

Elegant Downtown Apartments

4 out of 5
Price was $902, price is now $698 per person
$698
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)

5-night Grey Highlands vacations

Price found within the past 48 hours. Click for updated prices.
Cozy Rooms in Bright Walkout Suite - Newly Renovated 2026

Cozy Rooms in Bright Walkout Suite - Newly Renovated 2026

3 out of 5
Price was $634, price is now $585 per person
$585
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
Great Canadian Casino Resort Toronto

Great Canadian Casino Resort Toronto

4 out of 5
Price was $892, price is now $732 per person
$732
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
The Beverley Hotel

The Beverley Hotel

3.5 out of 5
Price was $1,084, price is now $892 per person
$892
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
TownePlace Suites by Marriott Toronto Northeast/Markham

TownePlace Suites by Marriott Toronto Northeast/Markham

3 out of 5
Price was $832, price is now $705 per person
$705
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
Staybridge Suites Toronto Airport East by IHG

Staybridge Suites Toronto Airport East by IHG

3 out of 5
Price was $1,006, price is now $868 per person
$868
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
Sandman Hotel Oakville

Sandman Hotel Oakville

3.5 out of 5
Price was $780, price is now $674 per person
$674
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
Spark by Hilton Toronto Mississauga

Spark by Hilton Toronto Mississauga

2.5 out of 5
Price was $808, price is now $708 per person
$708
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
Park Inn By Radisson Toronto - Markham

Park Inn By Radisson Toronto - Markham

3.5 out of 5
Price was $704, price is now $649 per person
$649
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
Monte Carlo Inn & Suites Downtown Markham

Monte Carlo Inn & Suites Downtown Markham

3 out of 5
Price was $728, price is now $671 per person
$671
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
Holiday Inn Express & Suites Milton by IHG

Holiday Inn Express & Suites Milton by IHG

2.5 out of 5
Price was $703, price is now $658 per person
$658
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
Maple leaf square

Maple leaf square

2 out of 5
Price was $976, price is now $922 per person
$922
per person
Oct 11 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)

6-7 night Grey Highlands vacations

Price found within the past 48 hours. Click for updated prices.
Finlay House Bed and Breakfast Niagara - on - the - Lake

Finlay House Bed and Breakfast Niagara - on - the - Lake

3.5 out of 5
Price was $1,096, price is now $767 per person
$767
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip flight included
Philipsburg (SXM) to Toronto (YYZ)
One King West Hotel & Residence

One King West Hotel & Residence

4 out of 5
Save 100% on your flight
Price was $1,722, price is now $1,242 per person
$1,242
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
Revery Toronto Downtown, Curio Collection by Hilton

Revery Toronto Downtown, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $2,098, price is now $1,528 per person
$1,528
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
Town Inn Suites Hotel

Town Inn Suites Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,592, price is now $1,165 per person
$1,165
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
Park Hyatt Toronto

Park Hyatt Toronto

5 out of 5
Save 100% on your flight
Price was $2,704, price is now $2,009 per person
$2,009
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
The Waterside Inn

The Waterside Inn

3.5 out of 5
Price was $1,387, price is now $1,033 per person
$1,033
per person
Oct 15 - Oct 21
found 23 hours ago
Roundtrip flight included
San Francisco (SFO) to Toronto (YYZ)
TOOR Hotel Toronto, part of JdV by Hyatt

TOOR Hotel Toronto, part of JdV by Hyatt

4 out of 5
Price was $1,676, price is now $1,270 per person
$1,270
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
Canopy By Hilton Toronto Yorkville

Canopy By Hilton Toronto Yorkville

4.5 out of 5
Price was $1,627, price is now $1,273 per person
$1,273
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
Embassy Suites by Hilton Toronto Airport

Embassy Suites by Hilton Toronto Airport

3.5 out of 5
Price was $1,131, price is now $886 per person
$886
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
Holiday Inn Toronto - Int'l Airport by IHG

Holiday Inn Toronto - Int'l Airport by IHG

3.5 out of 5
Price was $1,037, price is now $816 per person
$816
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
Element by Marriott Toronto Airport

Element by Marriott Toronto Airport

3.5 out of 5
Price was $1,062, price is now $841 per person
$841
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)
Toronto Marriott City Centre Hotel

Toronto Marriott City Centre Hotel

4 out of 5
Price was $1,853, price is now $1,474 per person
$1,474
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Toronto (YYZ)

Flight deals to Grey Highlands

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Oct 15 - Fri, Oct 23
YVR
Vancouver
YYZ
Toronto
$244 Roundtrip, found 1 day ago
$244
Roundtrip
found 1 day ago
Select Flair Airlines flight, departing Thu, Oct 15 from Vancouver to Toronto, returning Fri, Oct 23, priced at $244 found 1 day ago
Thu, Dec 3 - Sun, Dec 6
YVR
Vancouver
YTZ
Toronto
$315 Roundtrip, just found
$315
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Dec 3 from Vancouver to Toronto, returning Sun, Dec 6, priced at $315 just found
Thu, Dec 3 - Sun, Dec 6
YVR
Vancouver
YHM
Hamilton
$316 Roundtrip, just found
$316
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Dec 3 from Vancouver to Hamilton, returning Sun, Dec 6, priced at $316 just found

Top rated hotels for your Grey Highlands vacation

Leelas Villa Inn Flesherton

Leelas Villa Inn Flesherton

3 out of 5
774107 Highway 10 South Grey Highlands ON
5.35 mi from city center
$84 nightly
The price is $95 total per night
$95 total
Sep 2 - Sep 3
Total with taxes and fees
Located in Grey Highlands, Leelas Villa Inn Flesherton is within a 10-minute drive of Hoggs Falls and Eugenia Falls Conservation Area.
Free WiFi
Restaurant
Blue Mountain Resort Village Suites

Blue Mountain Resort Village Suites

4 out of 5
156 Jozo Weider Blvd The Blue Mountains ON
Free Cancellation
Reserve now, pay when you stay
17.24 mi from city center
$126 nightly
The price is $148 total per night
$148 total
Sep 30 - Oct 1
Total with taxes and fees
When you stay at Blue Mountain Resort Village Suites in The Blue Mountains, you'll be next to a golf course, just steps from Blue Mountain Ski Resort and Ridge Runner Mountain Coaster.
Pool
Hot Tub
Blue Mountain Resort Mosaic Suites

Blue Mountain Resort Mosaic Suites

2.5 out of 5
190 Jozo Weider Blvd The Blue Mountains ON
Free Cancellation
Reserve now, pay when you stay
17.35 mi from city center
$135 nightly
The price is $159 total per night
$159 total
Oct 1 - Oct 2
Total with taxes and fees
Located in The Blue Mountains, Blue Mountain Resort Mosaic Suites is just steps from Monterra Golf and 5 minutes by foot from Blue Mountain Ski Resort.
Pool
Spa
Don't see what you're looking for?
See all available properties in Grey Highlands
View all properties
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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.