Simcoe County Vacation Rentals

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Top Vacation Rentals in in Simcoe County

Holiday Hideout in Stayner
4 bedrooms, iron/ironing board, WiFi, bed sheets
Holiday Hideout in Stayner
The price is CA $299
CA $513 total
includes taxes & fees
Jun 25 - Jun 26
Holiday Hideout in Stayner
Exquisite Log Cabin Retreat- Perfect Couple’s Getaway! Tranquility at its best❤️
Fridge, microwave, oven, stovetop
Exquisite Log Cabin Retreat- Perfect Couple’s Getaway! Tranquility at its best❤️
10.0 out of 10, Exceptional, (257)
"Our stay was wonderful, the property better than advertised. So cozy and welcoming, nothing but peace and quiet. "
Exquisite Log Cabin Retreat- Perfect Couple’s Getaway! Tranquility at its best❤️
Dock Life Cottage 10 - Riverside, 2 Bedroom, Wasaga
Property grounds
Dock Life Cottage 10 - Riverside, 2 Bedroom, Wasaga
9.8 out of 10, Exceptional, (7)
"Very clean and kept up well. Just need a new shower head in the shower. It needs to tilt down more. We had a great time and ment great people. Made new friends and will be back next year."
The price is CA $193
CA $245 total
includes taxes & fees
Jun 25 - Jun 26
Dock Life Cottage 10 - Riverside, 2 Bedroom, Wasaga
The 1883 Century Flat- Collingwood, ON
Fridge, microwave, oven, stovetop
The 1883 Century Flat- Collingwood, ON
9.6 out of 10, Exceptional, (14)
"Our stay was short but it was perfect for our visit. Great location, though be warned it can be a little noisy with some loud cars, but nothing we weren’t already accustomed to. Would definitely stay again! "
The price is CA $114
CA $241 total
includes taxes & fees
Jun 25 - Jun 26
The 1883 Century Flat- Collingwood, ON
Vacation Escape ~Sauna~Fireplace ~BBQ~ Outdoor Fire-pit ~Ping pong
Interior
Vacation Escape ~Sauna~Fireplace ~BBQ~ Outdoor Fire-pit ~Ping pong
9.0 out of 10, Wonderful, (10)
"This was the perfect place for our semi-annual Girls chill weekend! Natalya was an excellent host and responded timely to all inquiries. You will 100% enjoy your stay here! Also, we happened to visit during a spring snow storm but the area is stunning no matter what time of year you choose to visit!"
Vacation Escape ~Sauna~Fireplace ~BBQ~ Outdoor Fire-pit ~Ping pong
The perfect get away by the Georgian Bay!
Beach nearby, sun loungers
The perfect get away by the Georgian Bay!
10.0 out of 10, Exceptional, (68)
"We love this spot! Thanks for everything!"
The perfect get away by the Georgian Bay!
Waterfront Muskoka with Pool & Hot Tub
Fridge, microwave, oven, stovetop
Waterfront Muskoka with Pool & Hot Tub
9.6 out of 10, Exceptional, (17)
"We had an amazing weekend here. The place was nice and clean and the host was very kind. The kids had a blast with all the toys and games available. I would definitely recommend to my friends. It was my first VRBO booking so naturally I was pretty anxious at first not hearing from them, but then once the check in information was provided, everything was nice and easy. Wonderful place to stay and an amazing host."
The price is CA $400
CA $711 total
includes taxes & fees
Jun 26 - Jun 27
Waterfront Muskoka with Pool & Hot Tub
Cottage tiny heaven.
Interior
Cottage tiny heaven.
9.4 out of 10, Exceptional, (12)
"We were a group of 14 extended family members who stayed here for 2 nights 3 days. Property was excellent, clean, and well stocked with everything you might need. We did have to use 2x of the provided air mattresses and pull-out sofa's to make enough beds for all of us - everyone was however very comfortable. The views from inside or on the deck are amazing, couldn't get enough of it! The rocky beach does make it a bit challenging to get in and out of the water especially for younger kids...
Cottage tiny heaven.
The Oake Room - Modern Convenience
1 bedroom, iron/ironing board, free WiFi, bed sheets
The Oake Room - Modern Convenience
10.0 out of 10, Exceptional, (4)
"Exceptional property! Clean, quiet, easy parking, quality bedding and furnishings. We were very happy with our stay and would stay here again in the future. "
The price is CA $120
CA $200 total
includes taxes & fees
Jun 25 - Jun 26
The Oake Room - Modern Convenience
Margarita Vacation Get Away
Indoor pool, outdoor pool, open noon to 8:00 PM, lifeguards on site
Margarita Vacation Get Away
3.5 star property
9.4 out of 10, Exceptional, (3)
"Clean and cozy property. Great communication from owner. However, pictures showed a jetted tub, larger suite, and rear facing patio (which we later learned were for the larger suite next door also owned by the owners who were fabulous.) I would suggest separating the two property pictures to avoid future confusion. "
Margarita Vacation Get Away
The Mansion, Wasaga beach, Blue mountain
Exterior
The Mansion, Wasaga beach, Blue mountain
10.0 out of 10, Exceptional, (2)
"Wali was an amazing host. Gave us a tour of the place when we got there to make sure we are comfortable. Would 100% book this place for our parents to come and enjoy in the summer time."
The price is CA $1,450
CA $2,494 total
includes taxes & fees
Jul 1 - Jul 2
The Mansion, Wasaga beach, Blue mountain
The Family Escape-5 min to the slopes & the shore!
Terrace/patio
The Family Escape-5 min to the slopes & the shore!
9.2 out of 10, Wonderful, (15)
"Property was well maintained, clean and check in was easy. The property was everything we needed for our golfing weekend for my husband's birthday. We ate dinner in the village on the first night and bbq'd the second night, it was very nice and conveniently located to golf courses."
The price is CA $139
CA $330 total
includes taxes & fees
Jun 26 - Jun 27
The Family Escape-5 min to the slopes & the shore!
Bed and Break fast home in Collingwood for 6 people
Property grounds
Bed and Break fast home in Collingwood for 6 people
9.8 out of 10, Exceptional, (6)
"We had a great stay at Devadasan’s place. The beds and couches were comfortable. We loved the breakfast offerings in the morning."
The price is CA $229
CA $293 total
includes taxes & fees
Jun 25 - Jun 26
Bed and Break fast home in Collingwood for 6 people
🌲The woodlands retreat🌲SLEEPS 20! HOT TUB! SAND VOLLEYBALL COURT
Fridge, microwave, oven, stovetop
🌲The woodlands retreat🌲SLEEPS 20! HOT TUB! SAND VOLLEYBALL COURT
10.0 out of 10, Exceptional, (10)
"A nice place that can hold many people. Very large yard. Country feeling while being basically in town. Very nice stream in the back."
The price is CA $999
CA $1,484 total
includes taxes & fees
Jul 3 - Jul 4
🌲The woodlands retreat🌲SLEEPS 20! HOT TUB! SAND VOLLEYBALL COURT
Dock Life Beach 1 - Cottage 12, Riverview, 1 Bedroom, 3 min walk to Beach 1
Property grounds
Dock Life Beach 1 - Cottage 12, Riverview, 1 Bedroom, 3 min walk to Beach 1
9.4 out of 10, Exceptional, (6)
"We had an amazing stay here ! The place was extremely clean. Quite location & just a quick walk to the main beach. The staff was very friendly as well. Would highly recommend and will stay at this place again if ever I head back to wasaga."
The price is CA $193
CA $245 total
includes taxes & fees
Jun 25 - Jun 26
Dock Life Beach 1 - Cottage 12, Riverview, 1 Bedroom, 3 min walk to Beach 1
COTTAGE #5
On the beach
COTTAGE #5
9.8 out of 10, Exceptional, (24)
"Super clean and great for communication. "
The price is CA $275
CA $614 total
includes taxes & fees
Jul 2 - Jul 3
COTTAGE #5
Lovely Water Front Cottage- pool,firepit and amenities near by & access to water
Outdoor pool
Lovely Water Front Cottage- pool,firepit and amenities near by & access to water
Lovely Water Front Cottage- pool,firepit and amenities near by & access to water
COZY COTTAGE WALKING DISTANCE TO LAKE SIMCOE & FRIDAY HARBOUR
Fridge, oven, stovetop, coffee/tea maker
COZY COTTAGE WALKING DISTANCE TO LAKE SIMCOE & FRIDAY HARBOUR
9.2 out of 10, Wonderful, (38)
"Wifi password wasnt available on site, it required to text the homeowner but they responded quickly."
COZY COTTAGE WALKING DISTANCE TO LAKE SIMCOE & FRIDAY HARBOUR
Lovely Water Front Cottage- pool,firepit and amenities near by & access to water
Fridge, microwave, oven, stovetop
Lovely Water Front Cottage- pool,firepit and amenities near by & access to water
10.0 out of 10, Exceptional, (1)
"This property exceeded our expectations! My friends and I had a blast staying here.The place is spotless, just as pictured, and stocked with everything we needed. It's in a safe, gated area, conveniently located near various towns and attractions. Levon's recommendations for winter activities were a plus. We extended our stay because we loved it, and the Levon was incredibly accommodating. A fantastic experience!"
Lovely Water Front Cottage- pool,firepit and amenities near by & access to water
Dock Life Cottage 4 - Riverside, 1 Bedroom, Wasaga
Property grounds
Dock Life Cottage 4 - Riverside, 1 Bedroom, Wasaga
9.6 out of 10, Exceptional, (9)
"Great relaxing stay, owner is very nice and attentive. I liked the rentable kayaks. Location is so peaceful. Cabins were nice and clean."
Dock Life Cottage 4 - Riverside, 1 Bedroom, Wasaga
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See all available 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.

Everything you need to know about Simcoe County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Simcoe County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Simcoe County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Simcoe County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Simcoe County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simcoe County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simcoe County vacation rentals we have selected for you start as low as CA $114 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Simcoe County rentals

At Expedia, we put the best Simcoe County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Simcoe County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Simcoe County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Simcoe County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Recent reviews in Simcoe County
Expedia verified reviews

Days Inn by Wyndham Orillia

Days Inn by Wyndham Orillia

5/5 Excellent
"facitity was clean and staff were friendly and professional."
A verified traveller stayed at Days Inn by Wyndham Orillia
Posted 5 hours ago
Days Inn by Wyndham Orillia