Simcoe County Vacations & Trips from $576
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Your Simcoe County Vacation
Answer the call of adventure with a customized vacation package to Simcoe County. Wherever it is you're going and whatever you have planned, get ready to immerse yourself in a destination with so much to offer. Trying to decide where to go during your trip to Simcoe County? Angus is a leading city that shouldn't be missed. Whether you're planning to travel on a shoestring or in the lap of luxury, Expedia are here to help you customize your next dream Simcoe County vacation.
Top destinations in Simcoe County
Collingwood
The Latest Simcoe County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Vine Ridge Resort
Save 100% on your flight
Price was $1,774, price is now $1,129 per person
$1,129
per person
Aug 13 - Aug 23
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Toronto (YYZ)
8.6/10 Excellent! (94 reviews)
We had ants in the kitchen. Contacted front desk twice, both times they said they would look into it and they never got back to me. The facility does not come with any linens, towels, etc. We were flying in from out of province and never received this notice until after we purchased a non-refundable stay. Paper towels were in the unit for the kitchen but when it was used up they said they don’t supply paper towel so we had nothing to wipe up with in kitchen. They had sprayed down the road with some solution that let the bottom of our shoes yucky even the next morning. Very poor experience.
Reviewed on Jun 6, 2026
Hotel Riu Plaza Toronto
Downtown Toronto
Price was $1,297, price is now $838 per person
$838
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Toronto (YYZ)
9.2/10 Wonderful! (3,388 reviews)
We had an excellent experience at Hotel Riu Plaza in Toronto! The rooms were fabulous, very clean, staff was friendly and helpful and the breakfast was exceptional!
Reviewed on Jun 7, 2026
Modern Downtown Apartments
Downtown Toronto
Price was $1,350, price is now $914 per person
$914
per person
Aug 15 - Aug 19
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Toronto (YYZ)
8.4/10 Very Good! (557 reviews)
Location and description were great.
Lack of response to clarify how to complete the deposit ahead of time; got back to me on the day of my check-in.
Very convenient place to stay, but note for the ladies, lighting is not favourable for makeup!
Reviewed on May 30, 2026
One King West Hotel & Residence
Downtown Toronto
Price was $1,115, price is now $762 per person
$762
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Toronto (YYZ)
9.4/10 Exceptional! (7,850 reviews)
Room was clean bathroom had a weird layout with the toilet behind the door lots of patchwork on ceiling and walls
Reviewed on Jun 7, 2026
Find the Best Simcoe County Vacation Packages
Simcoe County Essential Information
Language | English |
|---|---|
Currency | Canadian dollars |
Closest Airport | Pearson Intl. Airport (YYZ) |
Top Sights | Elmvale Jungle Zoo, Holland Marsh and Wye Marsh Wildlife Centre |
Simcoe County Hotel Deals
Living Water Resort and Spa
9 Harbour Street East Collingwood ON
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $177 total per night from Jun 8 to Jun 9
$177 total
Jun 8 - Jun 9
Total with taxes and fees
8.4/10 Very Good! (1,568 reviews)
"Outdoor hot tub and spa was good but it recommended to book the spa before you visit"
Reviewed on Jun 6, 2026
Living Stone Golf Resort
19 Keith Ave Collingwood ON
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $131 total per night from Jun 8 to Jun 9
$131 total
Jun 8 - Jun 9
Total with taxes and fees
8.2/10 Very Good! (1,256 reviews)
"It was better than the last time I was there"
Reviewed on Jun 3, 2026
Carriage Ridge Resort, an Ascend Collection Resort
3303 Line 3 N Oro-Medonte ON
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $97 total per night from Jun 28 to Jun 29
$97 total
Jun 28 - Jun 29
Total with taxes and fees
9/10 Wonderful! (1,007 reviews)
"Had a wonderful stay! The place was clean, comfortable, and well maintained. The staff was friendly and helpful throughout our visit. We really enjoyed the amenities and the peaceful atmosphere. Would definitely recommend and would love to come back again!!!!"
Reviewed on Jun 7, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
