Simcoe County Vacation Rentals

Compare and save

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Top Cities in Simcoe County

Featured Vacation Homes in Simcoe County

Our top choices for Simcoe County vacation homes

The Nordic -Central Collingwood Condo

3.0 star property
4.0 out of 10, (1)
"It is a shame that third party companies are offering properties with no sole, renting someones home should be an adventure"
The price is CA $111
CA $289 total
includes taxes & fees
Sep 21 - Sep 22
The Nordic -Central Collingwood Condo

Horseshoe Valley Suites - The Glade

4.0 star property
9.0 out of 10, Wonderful, (9)
"Great place to stay"
Horseshoe Valley Suites - The Glade

Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!

9.4 out of 10, Exceptional, (78)
"Great stay. Excellent location and beautiful outdoor area."
Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!

Vacation Escape ~Sauna~Fireplace ~BBQ~ Outdoor Fire-pit ~Ping pong

9.2 out of 10, Wonderful, (35)
"Rooms with multiple bed made it really easy and nice for our group of friends to stay. The main sitting area was nice to hang out. The extra fee for extra people was tough cause not everyone was able to come. "
Vacation Escape ~Sauna~Fireplace ~BBQ~ Outdoor Fire-pit ~Ping pong

Private Boyne River Cottage- steps to great fishing

Private Boyne River Cottage- steps to great fishing

Lakefront condo steps to the beach with pool, and fireplace

8.0 out of 10, Very good, (1)
"It was a wonderful stay! The place was comfortable and clean. I would suggest that the decks in the front and back be swept. There was a lot of spider webs and bugs on the siding and doors. A simple dusting with a broom would make a difference. Other than that, it was great!"
Lakefront condo steps to the beach with pool, and fireplace

New, Modern, Relaxing home in Collingwood. 3 bedroom, Sleeps 6.

10.0 out of 10, Exceptional, (11)
"R.S from VA USA Aug. 2025 Stayed 5 Days We had a fantastic stay in this place, definitely we will come back. "
New, Modern, Relaxing home in Collingwood. 3 bedroom, Sleeps 6.

Full Cottage STEPS 2 BEACH Drive 2 Blue Mountain

9.4 out of 10, Exceptional, (3)
"Had an amazing stay, the property was great, would visit again "
The price is CA $191
CA $569 total
includes taxes & fees
Sep 7 - Sep 8
Full Cottage STEPS 2 BEACH Drive 2 Blue Mountain

Cozy cottage with ping pong - short walk to the beach

9.6 out of 10, Exceptional, (4)
"Amazing location and beautiful beach nearby. Open concept living room/kitchen was ideal. Bed was very comfy and the A/C was so nice to have for our 4 night stay. Thanks!"
Cozy cottage with ping pong - short walk to the beach

Beach1. com - Beach House # 4 - Beachfront Wasanga Beach

9.0 out of 10, Wonderful, (2)
"Overall super. We have a few comments : 1- almost no water pressure in the kitchen sink, this must be fixed, really an irritant after a week. 2- all the sofas smelled very strong of wet dog. We had to use fabreez on the fabric twice to get it to a tolerable level. 3- on arrival we felt sand on all surfaces on the ground level (table, counters…), the cleaning crew must be carefull about this. 4- the upper level TV in the family room is not fonctionnal. Like I said, overall super, just a few...
Beach1. com - Beach House # 4 - Beachfront Wasanga Beach

Driftwood on 6th in Historic Downtown Collingwood/Pet Friendly

10.0 out of 10, Exceptional, (23)
"Very nice home and property for a relaxing stay. Convenient location for downtown access and going to other places."
Driftwood on 6th in Historic Downtown Collingwood/Pet Friendly

Casa Di Nonna

2.0 star property
Casa Di Nonna

Modern Luxury Retreat with Stunning Views & Open Concept Design

10.0 out of 10, Exceptional, (2)
Modern Luxury Retreat with Stunning Views & Open Concept Design

Vacation Home on Simcoe lake

Vacation Home on Simcoe lake

Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage

9.8 out of 10, Exceptional, (6)
"This rental was very affordable with lots of beds. We enjoyed our stay and had plenty of room for a larger group."
The price is CA $141
CA $427 total
includes taxes & fees
Sep 23 - Sep 24
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage

Spa Golf Bike Ski Refresh

9.6 out of 10, Exceptional, (5)
"This is a wonderful place to stay close to everything that you would need ! This unit was perfect for our ladies weekend away beautiful set up ! Very clean ! "
The price is CA $200
CA $503 total
includes taxes & fees
Aug 24 - Aug 25
Spa Golf Bike Ski Refresh

Cozy Newly Built Orillia Lakeside 5 Bedroom House! 3 minutes walk to the lake!

7.8 out of 10, Good, (7)
"The house was lovely and clean. It is a new build so the backyard is not finished, but otherwise it was really nice. Property management was quick to respond to all our questions and very helpful. Would recommend. "
The price is CA $194
CA $445 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Newly Built Orillia Lakeside 5 Bedroom House! 3 minutes walk to the lake!

Brand new waterfront LUXE lake house for a beautiful week/end away!

10.0 out of 10, Exceptional, (3)
"Host Ana is very very nice and respond very quickly! The place was cozy and nice lake view . Enjoy the Kayak here . I will book next year again !"
Brand new waterfront LUXE lake house for a beautiful week/end away!

Modern Home by Georgian Bay w/ hot tub. Pet friendly!!

9.4 out of 10, Exceptional, (3)
"Close to where we needed to be, clean, cool and spacious."
Modern Home by Georgian Bay w/ hot tub. Pet friendly!!

Luxurious Lake front Island Twnhome Friday Harbour

8.8 out of 10, Excellent, (9)
"We enjoyed our stay here during a major storm. The home was very welcoming and suited our needs . "
Luxurious Lake front Island Twnhome Friday Harbour
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Simcoe County Hotel Reviews