Holiday Rentals in Simcoe County
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Top Cities in Simcoe County
Collingwood
Wasaga Beach
Our top choices for Simcoe County holiday rentals
Condo in Oro-Medonte
Margarita Vacation Getaway9.8 out of 10, Exceptional, (13)
"Very nice accommodations.
Benjamin and Margarita were great hosts!
Thank you "
Selina
Cottage in Wasaga Beach
Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!7.4 out of 10, Good, (3)
"A fantastic stay. Thank you "
Mike B.
The price is €150
includes taxes & fees
11 Jan - 12 Jan 2026
Cabin in Collingwood
Exquisite Log Cabin Retreat- Perfect Couple’s Getaway! Tranquility at its best❤️10.0 out of 10, Exceptional, (321)
"Amazing property!"
Trish K.
Condo in Collingwood
Downtown Collingwood Condos9.2 out of 10, Wonderful, (18)
"Beautiful property "
Diane
The price is €291
includes taxes & fees
19 Dec - 20 Dec
Holiday Home in Alcona
6 Bedroom Executive Cottage near Lake Simcoe & Innisfil Beach Park9.8 out of 10, Exceptional, (87)
"Excellent property with loads of space. Comfortable beds and good quality furniture throughout. Just a short walk from the beach. Very impressed. Would recommend. "
stephanie h.
Holiday Home in Oro-Medonte
Horseshoe Valley Suites - The Glade9.0 out of 10, Wonderful, (9)
"Great place to stay"
Elizabeth
Cottage in Oro-medonte
A cozy family retreat surrounded by trees, Nature, comfort and family memories.8.8 out of 10, Excellent, (24)
"Host was great to work with and property was very clean!"
Morgan
The price is €451
includes taxes & fees
4 Jan - 5 Jan 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.
Top Simcoe County Hotel Reviews
Carriage Ridge Resort, an Ascend Collection Resort
10/10 Excellent
Find out more about Simcoe County
Holiday Homes in Simcoe County
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Look no further and take a look at our great range of rental properties in Simcoe County!