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Grey Highlands Vacation Packages

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Grey Highlands Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Waterside Inn

The Waterside Inn

3.5 out of 5
Price was $862, price is now $593 per person
$593
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Toronto (YYZ)
Book a stay at this business-friendly hotel in Mississauga. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Square One Shopping Centre and Lakefront Promenade Park are located nearby.
Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
Save 100% on your flight
Price was $1,839, price is now $1,110 per person
$1,110
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Toronto (YYZ)
Book a stay at this business-friendly hotel in Toronto. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Popular attractions CN Tower and Rogers Centre are located nearby.
The Hazelton Hotel Toronto

The Hazelton Hotel Toronto

5 out of 5
Save 100% on your flight
Price was $3,172, price is now $1,918 per person
$1,918
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Toronto (YYZ)
Book a stay at this luxury hotel in Toronto. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions CF Toronto Eaton Centre and CN Tower are located nearby.
GLOBALSTAY Modern 3 BD House in Brampton

GLOBALSTAY Modern 3 BD House in Brampton

4 out of 5
Save 100% on your flight
Price was $1,863, price is now $1,291 per person
$1,291
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Toronto (YYZ)
Book a stay at this business-friendly vacation home in Brampton. Enjoy free WiFi, free parking, and a garden. Popular attractions The Old Pro Driving Range and Historic Bovaird House are located nearby.
1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Price was $2,570, price is now $1,797 per person
$1,797
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Toronto (YYZ)
Book a stay at this luxury hotel in Toronto. Enjoy free WiFi, an outdoor pool, and 3 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rogers Centre and CN Tower are located nearby.
Mount Alverno Luxury Resorts

Mount Alverno Luxury Resorts

2.5 out of 5
Price was $1,092, price is now $789 per person
$789
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Toronto (YYZ)
Book a stay at this business-friendly hotel in Caledon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Sharon Lake and Island Lake Conservation Area are located nearby.
Hilton Toronto/Markham Suites Conference Centre & Spa

Hilton Toronto/Markham Suites Conference Centre & Spa

4 out of 5
Save 100% on your flight
Price was $1,279, price is now $930 per person
$930
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Toronto (YYZ)
Book a stay at this spa hotel in Markham. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Flato Markham Theatre and First Markham Place are located nearby.
The Briars Resort & Spa

The Briars Resort & Spa

3.5 out of 5
Price was $1,161, price is now $848 per person
$848
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Toronto (YYZ)
Book a stay at this beach hotel in Georgina. Enjoy free parking, a full-service spa, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions Bonnie Park and Briars Golf Club are located nearby.

Grey Highlands Vacation Packages 3-4 Night Stays

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
Old Town Historic District
Price was $1,048, price is now $769 per person
$769
per person
Jul 8 - Jul 11
found 5 hours ago
Roundtrip flight included
Chicago (ORD) to Toronto (YYZ)
Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
Downtown Toronto
Price was $1,236, price is now $836 per person
$836
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Toronto (YYZ)
Revery Toronto Downtown, Curio Collection by Hilton

Revery Toronto Downtown, Curio Collection by Hilton

4 out of 5
Downtown Toronto
Price was $1,417, price is now $1,025 per person
$1,025
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Toronto (YYZ)
The Sutton Place Hotel Toronto

The Sutton Place Hotel Toronto

4.5 out of 5
Downtown Toronto
Price was $1,329, price is now $987 per person
$987
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Toronto (YYZ)

Grey Highlands Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Waterside Inn

The Waterside Inn

3.5 out of 5
Port Credit
Price was $862, price is now $593 per person
$593
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Toronto (YYZ)
Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
Downtown Toronto
Save 100% on your flight
Price was $1,839, price is now $1,110 per person
$1,110
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Toronto (YYZ)
The Hazelton Hotel Toronto

The Hazelton Hotel Toronto

5 out of 5
Old Toronto
Save 100% on your flight
Price was $3,172, price is now $1,918 per person
$1,918
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Toronto (YYZ)
1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Price was $2,903, price is now $2,001 per person
$2,001
per person
Jul 1 - Jul 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Toronto (YYZ)

Top Flight Deals

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

Flair Airlines
Thu, Jul 16 - Thu, Jul 23
YXX
Abbotsford Intl.
YYZ
Pearson Intl.
$307 Roundtrip, found 2 days ago
$307
Roundtrip
found 2 days ago
Select Flair Airlines flight, departing Thu, Jul 16 from Abbotsford Intl. to Pearson Intl., returning Thu, Jul 23, priced at $307 found 2 days ago
Flair Airlines
Wed, Jul 8 - Mon, Jul 13
YVR
Vancouver Intl.
YYZ
Pearson Intl.
$322 Roundtrip, found 5 days ago
$322
Roundtrip
found 5 days ago
Select Flair Airlines flight, departing Wed, Jul 8 from Vancouver Intl. to Pearson Intl., returning Mon, Jul 13, priced at $322 found 5 days ago
Porter Airlines
Tue, Jul 7 - Thu, Jul 23
YVR
Vancouver Intl.
YHM
John C. Munro Hamilton Intl.
$355 Roundtrip, found 2 days ago
$355
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Tue, Jul 7 from Vancouver Intl. to John C. Munro Hamilton Intl., returning Thu, Jul 23, priced at $355 found 2 days ago
Air Canada
Wed, Oct 14 - Fri, Oct 23
LAX
Los Angeles Intl.
YYZ
Pearson Intl.
$439 Roundtrip, found 1 day ago
$439
Roundtrip
found 1 day ago
Select Air Canada flight, departing Wed, Oct 14 from Los Angeles Intl. to Pearson Intl., returning Fri, Oct 23, priced at $439 found 1 day ago