Vacation Rentals in Simcoe County
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Our top choices for Simcoe County vacation rentals
1. Downtown Collingwood Condos
Downtown Collingwood CondosCollingwood
9.0 out of 10, Wonderful, (43 reviews)
"This is a very cozy place!"
Zhaoqi
The price is ￥15,109
￥34,983 total
includes taxes & fees
Nov 8 - Nov 9
2. Stunning 1BR w Pool ~ Free Parking & Self Check-In
Stunning 1BR w Pool ~ Free Parking & Self Check-InInnisfil
10.0 out of 10, Exceptional, (5 reviews)
"Although our stay was short, we had a wonderful experience. The host was excellent at communicating and made everything easy and seamless. The place was very clean, comfortable, and easily accessible. We really enjoyed our stay and would definitely love to come back!"
lisa
The price is ￥16,349
￥31,088 total
includes taxes & fees
Nov 3 - Nov 4
3. Lux Studio in Horseshoe Valley
Lux Studio in Horseshoe ValleyOro
8.8 out of 10, Excellent, (5 reviews)
"Quiet location
Pool was close by
Community bbq
Trails nearby
Nice little apartment"
Sam
The price is ￥12,190
￥24,960 total
includes taxes & fees
Nov 3 - Nov 4
4. Lake View Loft Studio type
Lake View Loft Studio typeSevern
8.6 out of 10, Excellent, (9 reviews)
"The loft is spacious and well set up with quality furnishings and amenities. We were travelling further north the next day so it was convenient to the highway yet in a peaceful lakeside cottage setting."
Jason
The price is ￥19,957
￥32,362 total
includes taxes & fees
Nov 3 - Nov 4
5. Fiddlers Green at Evergreen Resort Wasaga Beach
Fiddlers Green at Evergreen Resort Wasaga BeachWasaga Beach
10.0 out of 10, Exceptional, (1 review)
"Jennifer provided exceptional customer service! What an incredible location and experience! We’ll be back!"
Patricia
The price is ￥14,263
￥39,733 total
includes taxes & fees
Nov 5 - Nov 6
6. Cozy 1-Bedroom Romantic Retreat with full Kitchen
Cozy 1-Bedroom Romantic Retreat with full KitchenOro-Medonte
10.0 out of 10, Exceptional, (1 review)
"What a wonderful place to stay! The hose was so welcoming from the first communication and throughout the trip. The property was exactly as described but maybe even nicer in person than the pictures. The condo was super spacious with loads of room in the main room plus the bedroom. And the bathroom! Wow! Definitely spa-like with a seperate tub and shower. Treasure is comfortable to hang out on. Instructions inside for pool and wifi were clear. The bed was super comfy! And the black out curtains...
Rayissa N.
The price is ￥10,571
￥24,012 total
includes taxes & fees
Nov 9 - Nov 10
7. Bright 2 Bedroom Entire Basement Apartment
Bright 2 Bedroom Entire Basement ApartmentAngus
9.0 out of 10, Wonderful, (14 reviews)
"Our stay was great! The host was responsive and very nice!
Would highly recommend!"
Julie
The price is ￥11,675
￥32,177 total
includes taxes & fees
Nov 3 - Nov 4
8. Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing
Horseshoe Valley Resort ,KING Bd 55”Tv Spa SkiingShanty Bay
8.8 out of 10, Excellent, (3 reviews)
"Excellent place to stay while enjoying the Valley."
Amy R.
The price is ￥19,577
￥35,764 total
includes taxes & fees
Nov 3 - Nov 4
9. Spacious Resort Studio in Collingwood - 9 Min from Blue Mountain!
Spacious Resort Studio in Collingwood - 9 Min from Blue Mountain!Collingwood
9.2 out of 10, Wonderful, (32 reviews)
"Place wqs great"
miguel c.
The price is ￥17,589
￥29,941 total
includes taxes & fees
Nov 3 - Nov 4
10. Bonnie 2 Cottage/Resort/Orillia, Muskoka
Bonnie 2 Cottage/Resort/Orillia, MuskokaWashago
9.0 out of 10, Wonderful, (2 reviews)
"Very nice and quiet place to relax. The pool was very clean with ample seating. The lake was across the road and so was the boat launch. I would definitely recommend this resort."
Luis F.
11. 124 Hurontario Unit 2
124 Hurontario Unit 2Collingwood
The price is ￥17,544
￥45,281 total
includes taxes & fees
Nov 3 - Nov 4
12. Dockhouse at Evergreen Resort in Wasaga Beach
Dockhouse at Evergreen Resort in Wasaga BeachWasaga Beach
10.0 out of 10, Exceptional, (2 reviews)
"Very nice and clean property. Disappointed about the pool not being heated."
Rita R.
13. Fire & Ice Spa w/ Private Sauna!
Fire & Ice Spa w/ Private Sauna!Innisfil
10.0 out of 10, Exceptional, (13 reviews)
"Great views in a warm, fire-lit setting—perfect spot for a night out."
Craig
The price is ￥21,342
￥42,559 total
includes taxes & fees
Nov 3 - Nov 4
14. Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game RoomOro Medonte
9.8 out of 10, Exceptional, (11 reviews)
"Fantastic stay.
We had great service from the host and enjoyed the design. It's easy to see that a lot of effort was put into the decor. We felt very at home and would definitely stay there again."
Travis
The price is ￥14,641
￥38,714 total
includes taxes & fees
Nov 9 - Nov 10
15. Vacation Inn Townhomes
Vacation Inn TownhomesCollingwood
8.4 out of 10, Very good, (7 reviews)
"This is great property and located in a beautiful area! It was nice and clean and we loved our stay! Highly recommend the place!!!"
Madushi
The price is ￥17,589
￥52,473 total
includes taxes & fees
Nov 3 - Nov 4
16. Pony Trail Haven Near Blue Mountain & Scenic Trails
Pony Trail Haven Near Blue Mountain & Scenic TrailsCollingwood
The price is ￥21,938
￥54,364 total
includes taxes & fees
Nov 3 - Nov 4
17. Lakeview private suite with kitchen (Twin or King)
Lakeview private suite with kitchen (Twin or King)Loretto
8.6 out of 10, Excellent, (8 reviews)
"Beautiful spot to stay! Highly recommended "
Patrick S.
The price is ￥13,530
￥21,277 total
includes taxes & fees
Nov 3 - Nov 4
18. Oasis Spa w/ Private Sauna!
Oasis Spa w/ Private Sauna!Innisfil
10.0 out of 10, Exceptional, (1 review)
"The Oasis Spa Getaway was a fantastic two night stay for my partner and I. The property was clean, modern and cozy! The unit had everything a couple needs for their stay including a sauna within the unit and a beautiful balcony. The host Michelle provided exceptional hospitality and was easy to connect with when needed. The location is great and only a short walk to the boardwalk and a quick two minute drive to the Nest golf course. The building’s pool was easy to access, quiet, and relaxing....
Matthew K.
The price is ￥20,205
￥39,455 total
includes taxes & fees
Nov 3 - Nov 4
19. 124 Hurontario Unit 4
124 Hurontario Unit 4Collingwood
9.4 out of 10, Exceptional, (3 reviews)
"Quaint, clean, comfortable, centrally located. I'd happily stay here again."
Claude
The price is ￥15,650
￥39,487 total
includes taxes & fees
Nov 3 - Nov 4
20. Upscale Spa Getaway w/ Private Sauna
Upscale Spa Getaway w/ Private SaunaInnisfil
The price is ￥20,205
￥39,455 total
includes taxes & fees
Nov 3 - Nov 4
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.
Find vacation rentals that suit your style
Cottages
Cabins
Save an average of 15% on thousands of hotels when you're signed in
Top Simcoe County Hotel Reviews
Kings Inn Midland
8/10 Good
Find out more about Simcoe County
Vacation Apartments in Simcoe County
Search for Vacation rentals in Simcoe County on Expedia! You can easily find your home rentals, villas, Vacation apartments in Simcoe County using one of the methods below:
- View our selection of featured Vacation rentals in Simcoe County
- Use the map to find apartments and other Vacation homes in the Simcoe County neighbourhood you prefer
- Enter your travel dates to view the best deals on Vacation rentals in Simcoe County while they last
Look no further and take a look at our great range of rental properties in Simcoe County!