A marina with modern buildings, calm water, and a clear blue sky.

Vacation Rentals in Simcoe County

Top Cities in Simcoe County

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

Collingwood

Collingwood

Our top choices for Simcoe County vacation rentals

A modern kitchen with a large window, built-in appliances, and a central island.

1. Downtown Collingwood Condos

Downtown Collingwood Condos
3.0 star property
Collingwood
9.0 out of 10, Wonderful, (42 reviews)
"This is a very nice condo right downtown. Close to restaurants and shopping. It was nice to have a kitchen and all the amenities. We would definitely book this again. Communication with owner was always a quick response. A great place to stay!!"
Canada
Benny
$186 nightly
The price is $218
Oct 18 - Oct 19
Total with taxes and fees
Downtown Collingwood Condos
A rustic cabin with a stone chimney, wooden exterior, and a seating area with Adirondack chairs.

2. Guest house close to Blue Mountain, Wasaga Beach and Collingwood!

Guest house close to Blue Mountain, Wasaga Beach and Collingwood!
Nottawa
10.0 out of 10, Exceptional, (46 reviews)
"Great place to stay!"
Canada
Christopher
$217 nightly
The price is $245
Oct 20 - Oct 21
Total with taxes and fees
Guest house close to Blue Mountain, Wasaga Beach and Collingwood!
An aerial view of a resort with multiple swimming pools, outdoor seating areas, and a large building with a distinctive roof.

3. Lux Studio in Horseshoe Valley

Lux Studio in Horseshoe Valley
Oro
8.8 out of 10, Excellent, (3 reviews)
"Quiet location Pool was close by Community bbq Trails nearby Nice little apartment"
Canada
Sam
$152 nightly
The price is $164
Oct 18 - Oct 19
Total with taxes and fees
Lux Studio in Horseshoe Valley
A lakeside view with three lounge chairs, a small table, and a stone wall.

4. Lake View Loft Studio type

Lake View Loft Studio type
Severn
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."
Canada
Jason
$197 nightly
The price is $222
Oct 18 - Oct 19
Total with taxes and fees
Lake View Loft Studio type
An indoor swimming pool with clear glass walls, a separate hot tub area, and lounge chairs along the side.

5. Cozy 1-Bedroom Romantic Retreat with full Kitchen

Cozy 1-Bedroom Romantic Retreat with full Kitchen
Oro-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...
United States
Rayissa N.
$156 nightly
The price is $158
Oct 25 - Oct 26
Total with taxes and fees
Cozy 1-Bedroom Romantic Retreat with full Kitchen
A quaint building with a green exterior, a sign reading 'Weed It and Hop,' and a patio with outdoor seating.

6. Fiddlers Green at Evergreen Resort Wasaga Beach

Fiddlers Green at Evergreen Resort Wasaga Beach
Wasaga Beach
10.0 out of 10, Exceptional, (1 review)
"Jennifer provided exceptional customer service! What an incredible location and experience! We’ll be back!"
Canada
Patricia
$229 nightly
The price is $246
Oct 17 - Oct 18
Total with taxes and fees
Fiddlers Green at Evergreen Resort Wasaga Beach
A wooden deck with chairs and tables overlooking a lake, a flag, and a gazebo.

7. 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 "
United States
Patrick S.
$125 nightly
The price is $141
Oct 18 - Oct 19
Total with taxes and fees
Lakeview private suite with kitchen (Twin or King)
A modern living room with a gray sofa, wooden coffee table, and a dining area with a wooden table and chairs.

8. 124 Hurontario Unit 1

124 Hurontario Unit 1
Collingwood
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful place in a great location! Would definitely stay again!!"
Canada
Jo-Anne
$254 nightly
The price is $288
Oct 20 - Oct 21
Total with taxes and fees
124 Hurontario Unit 1
A hotel room with two beds, a large window with curtains, a ceiling fan, and a painting on the wall.

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, (31 reviews)
"Place wqs great"
United States
miguel c.
$173 nightly
The price is $195
Oct 19 - Oct 20
Total with taxes and fees
Spacious Resort Studio in Collingwood - 9 Min from Blue Mountain!
A modern kitchen with a central island, wooden staircase, and a dining area with white chairs.

10. Vacation Inn Townhomes

Vacation Inn Townhomes
4.0 star property
Collingwood
8.4 out of 10, Very good, (7 reviews)
"The property was very clean and exactly as described. It was centrally located to all amenities and attractions in the area. I would definitely stay here again. Excellent all around!"
Canada
Linda
$278 nightly
The price is $327
Oct 20 - Oct 21
Total with taxes and fees
Vacation Inn Townhomes
A wooden deck with a railing, two chairs, and a view of trees and water.

11. Tamarack Marina Waterfront Suite with Marina Views. Sauna Included!

Tamarack Marina Waterfront Suite with Marina Views. Sauna Included!
Coldwater
5.0 out of 10, (2 reviews)
"Amazing area by the lake the property manager was helpful when we spoke to him with simple requests. I hope the company that manages this marina checks on the maintenance of the cottages before or after when clients book.The cottage was clean when we arrived. Kudos to the cleaners"
United States
Vicky S.
$272 nightly
The price is $307
Oct 25 - Oct 26
Total with taxes and fees
Tamarack Marina Waterfront Suite with Marina Views. Sauna Included!
An aerial view of a resort with multiple swimming pools, outdoor seating areas, and a large building with a distinctive roof.

12. Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing

Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing
Shanty Bay
8.8 out of 10, Excellent, (3 reviews)
"Excellent place to stay while enjoying the Valley."
United States
Amy R.
$215 nightly
The price is $234
Oct 21 - Oct 22
Total with taxes and fees
Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing
A house with a blue door and a wooden deck.

13. The Little Lake House-Cozy 2Bdrm

The Little Lake House-Cozy 2Bdrm
Midland
9.2 out of 10, Wonderful, (10 reviews)
"Property was great. Super clean, very accurate description. Location is close to everything and good if you have others things you are doing in town or visiting people."
Canada
Danielle
$212 nightly
The price is $239
Nov 2 - Nov 3
Total with taxes and fees
The Little Lake House-Cozy 2Bdrm
A compact kitchen with a stainless steel refrigerator, a sink, and wooden cabinets.

14. 124 Hurontario Unit 4

124 Hurontario Unit 4
Collingwood
9.0 out of 10, Wonderful, (2 reviews)
"Quaint, clean, comfortable, centrally located. I'd happily stay here again."
Canada
Claude
$222 nightly
The price is $251
Nov 2 - Nov 3
Total with taxes and fees
124 Hurontario Unit 4
A modern living room with a TV, a round coffee table, a sofa, and a view of a cityscape through large windows.

15. Stunning 1BR w Pool ~ Free Parking & Self Check-In

Stunning 1BR w Pool ~ Free Parking & Self Check-In
Innisfil
10.0 out of 10, Exceptional, (3 reviews)
"This place was immaculate. Host was always super responsive. Had everything we needed. Highly recommend. We really enjoyed our stay."
Canada
Jennifer
$189 nightly
The price is $214
Oct 19 - Oct 20
Total with taxes and fees
Stunning 1BR w Pool ~ Free Parking & Self Check-In
A beach with wet sand and waves, a sunset in the background, and a clear sky.

16. Pony Trail Haven Near Blue Mountain & Scenic Trails

Pony Trail Haven Near Blue Mountain & Scenic Trails
Collingwood
$307 nightly
The price is $349
Oct 18 - Oct 19
Total with taxes and fees
Pony Trail Haven Near Blue Mountain & Scenic Trails
A modern living room with a wooden dining table, a sofa, and a television.

17. Bright 2 Bedroom Entire Basement Apartment

Bright 2 Bedroom Entire Basement Apartment
Angus
9.0 out of 10, Wonderful, (13 reviews)
"Great place"
United States
Adriano A.
$195 nightly
The price is $220
Oct 18 - Oct 19
Total with taxes and fees
Bright 2 Bedroom Entire Basement Apartment
A glass table with a champagne bucket and glasses on a balcony with string lights.

18. 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."
Canada
Craig
$271 nightly
The price is $292
Oct 21 - Oct 22
Total with taxes and fees
Fire & Ice Spa w/ Private Sauna!
A swimming pool with a fenced deck area, surrounded by trees and a view of a lake.

19. Bonnie 2 Cottage/Resort/Orillia, Muskoka

Bonnie 2 Cottage/Resort/Orillia, Muskoka
Washago
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."
United States
Luis F.
$194 nightly
The price is $219
Oct 21 - Oct 22
Total with taxes and fees
Bonnie 2 Cottage/Resort/Orillia, Muskoka
A spacious hallway with a neutral color scheme, a beige sofa, and a shower area with a glass door.

20. Clean & Cozy Home Near Downtown

Clean & Cozy Home Near Downtown
New Tecumseth
8.6 out of 10, Excellent, (7 reviews)
"Very cozy stay for a weekend hockey tournament."
Canada
Suzanne
$173 nightly
The price is $195
Oct 19 - Oct 20
Total with taxes and fees
Clean & Cozy Home Near Downtown
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.
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Top Simcoe County Hotel Reviews

Comfort Inn & Suites

Comfort Inn & Suites

8/10 Good
"The hallways need to be updated. The room cooling vents were dirty"
Tammy 1-night trip
Posted 2 hours ago
Comfort Inn & Suites

Find out more about Simcoe County

Discover your perfect Simcoe County vacation rental with Expedia

How many vacation rentals are available in Simcoe County?


Expedia has plenty of vacation rentals to choose from in and around  Simcoe County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Simcoe County?


The selection of Simcoe County vacation rentals we have selected for you start as low as $164 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Simcoe County?


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Why should I choose a vacation rental in Simcoe County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. 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. 


How do I find the best deal on a vacation rental in Simcoe County?


Find vacation rentals in Simcoe County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Simcoe County.  


What amenities are available in a vacation rental in Simcoe County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Simcoe County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Simcoe County?   


Everytime is a great time to head to Simcoe County! Staying in a Simcoe County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Simcoe County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Simcoe County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Simcoe County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Simcoe County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.