Simcoe County Vacations & Trips from ￥294,638

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Top destinations in Simcoe County

FlightsFlightsHotelsHotels

Collingwood

Collingwood
Aerial view of Wasaga Beach, Canada
FlightsFlightsHotelsHotels

Oro-Medonte

Oro-Medonte

The Latest Simcoe County Vacation Packages

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 ￥347,746, price is now ￥294,638 per person
￥294,638
per person
Aug 5 - Aug 9
found 10 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Toronto (YYZ)
8.6/10 Excellent! (1,018 reviews)
The room was spacious and the location of the hotel was perfect. Close to the water and shops and restaurants and the train to Toronto.

Reviewed on Jun 16, 2026

Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
Downtown Toronto
Price was ￥449,198, price is now ￥355,016 per person
￥355,016
per person
Aug 5 - Aug 9
found 10 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Toronto (YYZ)
9.2/10 Wonderful! (3,600 reviews)
Nice rooms /excellent breakfast

Reviewed on Jun 18, 2026

Sterling Inn & Spa - an Ontario's Finest Inn

Sterling Inn & Spa - an Ontario's Finest Inn

4 out of 5
Clifton Hill
Price was ￥558,402, price is now ￥455,115 per person
￥455,115
per person
Aug 7 - Aug 17
found 9 hours ago
Roundtrip flight included
Osaka (OSA) to Toronto (YYZ)
9.6/10 Exceptional! (2,415 reviews)
Great location and very friendly and helpful staff.

Reviewed on Jun 18, 2026

South Landing Inn Niagara on the Lake

South Landing Inn Niagara on the Lake

3.5 out of 5
Queenston
Price was ￥620,796, price is now ￥514,934 per person
￥514,934
per person
Aug 7 - Aug 17
found 9 hours ago
Roundtrip flight included
Osaka (OSA) to Toronto (YYZ)
10/10 Exceptional! (111 reviews)
Wonderful old inn.. Beautiful balconies.. Great amenities..

Reviewed on Jun 11, 2026

Cambridge Suites Toronto

Cambridge Suites Toronto

4 out of 5
Downtown Toronto
Price was ￥424,232, price is now ￥354,416 per person
￥354,416
per person
Aug 5 - Aug 9
found 10 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Toronto (YYZ)
9.2/10 Wonderful! (8,114 reviews)
This is not our first stay at this property. The bed was so comfortable! Time to start upgrading the rooms. Doors showed signs of water damage and time to move forward with getting rid of carpet.go laminate.

Reviewed on Jun 18, 2026

Simcoe County Hotel Deals

Living Water Resort and Spa

Living Water Resort and Spa

3.5 out of 5
9 Harbour Street East Collingwood ON
The price is ￥21,872 per night from Jun 21 to Jun 22
￥21,872
￥27,023 total
Jun 21 - Jun 22
includes taxes & fees
8.4/10 Very Good! (1,569 reviews)
"The staff was very friendly and helpful and made our anniversary extra special from the reception to the spa to the restaurant. The bed was so comfortable! Would definitely return’"

Reviewed on Jun 18, 2026

Living Water Resort and Spa
Living Stone Golf Resort

Living Stone Golf Resort

3 out of 5
19 Keith Ave Collingwood ON
Fully refundableReserve now, pay when you stay
The price is ￥15,583 per night from Jun 21 to Jun 22
￥15,583
￥19,481 total
Jun 21 - Jun 22
includes taxes & fees
8.2/10 Very Good! (1,253 reviews)
"Parking is ample, staff were very helpful & friendly. Only thing missing is a restaurant on site."

Reviewed on Jun 18, 2026

Living Stone Golf Resort
Carriage Ridge Resort, an Ascend Collection Resort

Carriage Ridge Resort, an Ascend Collection Resort

2.5 out of 5
3303 Line 3 N Oro-Medonte ON
Fully refundableReserve now, pay when you stay
The price is ￥13,955 per night from Jun 21 to Jun 22
￥13,955
￥16,243 total
Jun 21 - Jun 22
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"clean room! very quiet at nightime!"

Reviewed on Jun 16, 2026

Carriage Ridge Resort, an Ascend Collection Resort
See all 1,314 properties in Simcoe County
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.

Frequently asked questions

How much does a Simcoe County vacation package cost?
Get ready to book, because a getaway to Simcoe County starts from an affordable ￥294,638. When you combine your flights, hotels and more into a vacation package, you'll land the biggest bargains.
How do I get a cheap travel package to Simcoe County?
Find flights that suit your schedule, add a hotel room to your booking and see how much you save with a Simcoe County vacation package. It's as easy as that! From hotels and flights to rental cars and activities, Expedia is where your cheap getaway begins. And with more than 550 airlines and 1,000,000 hotels across the globe to select from, you won't be short of choice.
What are the top hotels in Simcoe County?
When it comes to properties in Collingwood, Fairfield Inn & Suites by Marriott Barrie and Hampton Inn & Suites Barrie are two fantastic options. If you're also spending time in Innisfil, Days Inn & Suites by Wyndham Collingwood and Living Stone Golf Resort look forward to welcoming you.
How far in advance should I book my Simcoe County vacation?
To bag rock-bottom prices, book early. Air carriers usually advertise flight tickets, along with some of the lowest fares, nearly a year ahead of time. Hotels, experiences and car rental should also be booked early so you can have the pick of the bunch. If you were hoping for a last-minute getaway in Simcoe County, there are always plenty of great deals to be had on Expedia. Book your escape today!
What does an Expedia Simcoe County travel package include?
Hotels, rental cars and flights, or any combination of the three — it's your choice. Whether you're exploring Simcoe County with the family or adventuring with your friends, there's a package to suit your budget and style. Once you've made your booking, why not add on a few activities?
What should I know before booking a Simcoe County travel package?
Booking all the parts of your trip together is an excellent way to save. Bundle your car rentals, airfares and hotels into a handy package. But it's not just hotels. Expedia features all sorts of properties, including vacation rentals such as oceanfront condos and short-term homes. The list is almost endless!
Can I choose my airline with a Simcoe County Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You're in charge! We have access to more than 550 partner airlines across the globe, so you have lots of choice when arranging your Simcoe County adventure.
If I'm not able to travel, can I cancel my Simcoe County vacation package?
If your vacation plans in Simcoe County have changed, it's good to know that you can amend or cancel your booking. If you booked less than 24 hours ago, you may be able to receive a refund. If your booking is older than that, your hotel, airline or car rental company may charge fees. To learn more, visit our Customer Service Portal.

Stay near popular Simcoe County attractions

A multi-tiered waterfall cascading over rocky terrain with a coniferous tree in the background.

Casino Rama

8.8/5 (718 reviews)
Why not roll the dice by visiting Casino Rama where you can enjoy the games and entertainment of this top casino in Chippewas of Rama First Nation? Discover the area's great live music and casinos.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.