Simcoe County Vacations & Trips from $506

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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

A historic brick building with green shutters and a sign for 'Arcade'.

Collingwood

Collingwood
A rocky shoreline with seagulls and a large rock formation extending into the water.

Tiny

Tiny
A beach with people relaxing and playing in the sand, waves crashing onto the shore, and a clear sky.

Wasaga Beach

Wasaga Beach
A kayaker in a turquoise sea near a rocky cliff.

Midland

Midland
An aerial view of a beach with a forested area and a clear sky.

Oro-Medonte

Oro-Medonte
A river winding through a dense forest with a bridge and boats.

Severn

Severn
A lake with a boat-shaped island, a parking lot, and a residential area with houses and trees.

Ramara

Ramara

The Latest Simcoe County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sterling Inn & Spa - an Ontario's Finest Inn

Sterling Inn & Spa - an Ontario's Finest Inn

Clifton Hill
$506
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
9.6/10 Exceptional! (2,495 reviews)
The room had a mold smell to it and the air conditioner unit was very close in/near the room. Very loud!

Reviewed on Sep 19, 2026

Spectacular Views Apartments

Spectacular Views Apartments

Downtown Toronto
Save 100% on your flight
$793
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
8.8/10 Excellent! (52 reviews)
1 Hotel Toronto

1 Hotel Toronto

Downtown Toronto
$835
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
9.6/10 Exceptional! (792 reviews)
Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

Downtown Toronto
$561
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
9.4/10 Exceptional! (4,688 reviews)
The Brick Hotel

The Brick Hotel

Old Toronto
Save 100% on your flight
$729
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Toronto (YYZ)
9.8/10 Exceptional! (16 reviews)
Très belle emplacement et restaurant proche et pas trop loin du Roger center

Reviewed on Sep 13, 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 Stone Golf Resort

Living Stone Golf Resort

19 Keith Ave Collingwood ON
Fully refundableReserve now, pay when you stay
$90 nightly
$105 total
Sep 27 - Sep 28
Total with taxes and fees
Living Stone Golf Resort
Carriage Ridge Resort, an Ascend Collection Resort

Carriage Ridge Resort, an Ascend Collection Resort

3303 Line 3 N Oro-Medonte ON
Fully refundableReserve now, pay when you stay
$79 nightly
$89 total
Oct 18 - Oct 19
Total with taxes and fees
8.8/10 Excellent! (1,010 reviews)
"Perfect situation especially for a family with the ability to make snacks, swim and play to keep them busy. A little outdated the rooms but still in good shape"

Reviewed on Sep 19, 2026

Carriage Ridge Resort, an Ascend Collection Resort
Living Water Resort and Spa

Living Water Resort and Spa

9 Harbour Street East Collingwood ON
$146 nightly
$172 total
Sep 20 - Sep 21
Total with taxes and fees
Living Water Resort and Spa
See all 1,258 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.

Stay near popular Simcoe County attractions

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

Casino Rama

8.8/10 (718 reviews)
Why not roll the dice with a visit to Casino Rama during your travels in Chippewas of Rama First Nation? Discover the area's great live music and casinos.
See properties
An aerial view of a park with a large building complex, a lake, and surrounding forested areas.

Horseshoe Valley

8.8/10 (352 reviews)
Hit the slopes in Oro-Medonte with a visit to Horseshoe Valley. Attend a sporting event in this family-friendly area, or seek out the adventure tours.
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A rural landscape with a stone house and a barn.
Photo by Evan Davis

Mount St. Louis Moonstone

8.4/10 (157 reviews)
Hit the slopes in Oro-Medonte with a visit to Mount St. Louis Moonstone. While in this family-friendly area, find time to visit its casinos.
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A wooden beach shelter with a bench and a trash bin.

Wasaga Beach Provincial Park

8.8/10 (445 reviews)
Explore hiking trails, relax on one of the world’s longest freshwater beaches and visit a historic site at this picturesque park.
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A ski lift in a snowy mountain town with buildings and snow-covered trees.

Snow Valley Ski Resort

8.6/10 (199 reviews)
Hit the slopes in Springwater with a visit to Snow Valley Ski Resort. While in this family-friendly area, you can savor the top-notch restaurants.
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Nottawasaga Inn Resort Golf Club

8.0/10 (48 reviews)
Enjoy a round of golf in New Tecumseth at Nottawasaga Inn Resort Golf Club. Make time to visit the casinos and spas while you're in the area.
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CFB Borden Military Museum

8.2/10 (19 reviews)
You can spend an afternoon exploring the galleries in CFB Borden Military Museum during your travels in Essa. While in this family-friendly area, you can savor the top-notch restaurants.
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Vettä Nordic Spa

You can take time to visit Vettä Nordic Spa during your travels to Oro-Medonte. You can seek out the ski slopes and golf courses in this relaxing area.
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What to do in Simcoe County

Smartphone Audio Driving Tour between Wasaga Beach and Toronto

Smartphone Audio Driving Tour between Wasaga Beach and Toronto

$6
per traveler
Smartphone Audio Driving Tour between Wasaga Beach and Toronto
Private 4 Day Algonquin Park Backcountry Canoe Trip

Private 4 Day Algonquin Park Backcountry Canoe Trip

$1,025
per adult
Private 4 Day Algonquin Park Backcountry Canoe Trip
See all activities in Simcoe County
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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.