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

Simcoe County Holiday Rentals

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Top Cities in Simcoe County

A historic brick building with green shutters and a sign for 'Arcade'.
Holiday RentalsHoliday Rentals

Collingwood

Collingwood
A kayaker in a turquoise sea near a rocky cliff.
Holiday RentalsHoliday Rentals

Midland

Midland

Our top choices for Simcoe County holiday 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, (41 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
The price is AU$346
includes taxes & fees
12 Oct - 13 Oct
Downtown Collingwood Condos
A modern kitchen with a central island, wooden staircase, and a dining area with white chairs.

2. 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
The price is AU$473
includes taxes & fees
13 Oct - 14 Oct
Vacation Inn Townhomes
A spacious living area with a fireplace, a large window, and a kitchen with a bar.

3. Historic Snowbridge Townhomes

Historic Snowbridge Townhomes
3.5 star property
The Blue Mountains
9.4 out of 10, Exceptional, (173 reviews)
"We absolutely loved our stay.. it was perfect for a little family vacation with our adult children and our 18month old granddaughter.. it had everything we could need and was spacious for together time and also lovely rooms for quiet time too.. close to the village but away just enough that it’s not crazy. Would definitely stay again!"
Canada
Joelle
The price is AU$400
includes taxes & fees
19 Oct - 20 Oct
Historic Snowbridge Townhomes
A cobblestone street lined with historic buildings, a prominent tower, and outdoor seating areas.

4. Rivergrass Condos

Rivergrass Condos
3.5 star property
The Blue Mountains
9.0 out of 10, Wonderful, (356 reviews)
"Nice place to stay."
Canada
Stephanie
The price is AU$365
includes taxes & fees
28 Oct - 29 Oct
Rivergrass Condos
A modern kitchen with a marble countertop and a built-in sink, a grey sofa with cushions, and a flat-screen TV mounted on the wall.

5. Crosswinds Townhomes

Crosswinds Townhomes
3.0 star property
The Blue Mountains
9.4 out of 10, Exceptional, (27 reviews)
"We enjoyed our stay! Beautiful property"
Canada
Marianna
The price is AU$393
includes taxes & fees
28 Oct - 29 Oct
Crosswinds Townhomes
A spacious living room with a fireplace, a large window, and a television.

6. Wintergreen Condos

Wintergreen Condos
3.5 star property
The Blue Mountains
8.6 out of 10, Excellent, (38 reviews)
"We had a great stay! The place was very clean and comfortable, with beautiful surroundings and a peaceful view overlooking the golf course. My kids especially loved the bunk beds, and the hot tub was a great bonus. I can imagine this place would be even more amazing in the winter for a ski trip. We really enjoyed our stay and would definitely come back!"
Canada
Xiuqing
The price is AU$582
includes taxes & fees
14 Oct - 15 Oct
Wintergreen Condos
A modern kitchen with a large island, wooden bar stools, a dining table, and a view of the outside.

7. North Creek Condos

North Creek Condos
3.5 star property
Craigleith
8.6 out of 10, Excellent, (205 reviews)
"The resort is absolutely beautiful, my wife and I loved it. Looking forward to next time"
Canada
Tenzin
The price is AU$263
includes taxes & fees
8 Nov - 9 Nov
North Creek Condos
A modern living room with a fireplace, a flat-screen TV, a dining area, and large windows offering a view of the outdoors.

8. Chateau Ridge Chalets

Chateau Ridge Chalets
3.5 star property
The Blue Mountains
9.0 out of 10, Wonderful, (200 reviews)
"Enjoyed our stay"
Canada
Ismat
The price is AU$443
includes taxes & fees
13 Oct - 14 Oct
Chateau Ridge Chalets
A spacious living room with a fireplace, a staircase, and a TV mounted on a wooden wall.

9. Liisa's Lodge

Liisa's Lodge
4.0 star property
The Blue Mountains
10.0 out of 10, Exceptional, (1 review)
"Great space"
Canada
Kara
The price is AU$1,232
includes taxes & fees
16 Oct - 17 Oct
Liisa's Lodge
A dining area with a large table set for 10, surrounded by chairs, with a view of a red deck through glass doors.

10. Mountain Views, Steps to BM Village, Hot Tub, BBQ.

Mountain Views, Steps to BM Village, Hot Tub, BBQ.
3.5 star property
The Blue Mountains
8.4 out of 10, Very good, (6 reviews)
"Had a great time here for my brother in law bachelor weekend"
Canada
Anonymous traveller
The price is AU$806
includes taxes & fees
13 Oct - 14 Oct
Mountain Views, Steps to BM Village, Hot Tub, BBQ.
A bedroom with a bed, a sofa, a dining area with chairs, and a kitchen in the background.

11. Slopeside Studio Wifi Towels Ski in Out

Slopeside Studio Wifi Towels Ski in Out
2.5 star property
Craigleith
8.0 out of 10, Very good, (3 reviews)
"Nice Little studio! Nice pool."
Canada
Kimberly
The price is AU$84
includes taxes & fees
8 Nov - 9 Nov
Slopeside Studio Wifi Towels Ski in Out
A living room with a beige sofa, a wooden ceiling beam, and a large window with blinds.

12. Ski In Ski Out Cozy Studio

Ski In Ski Out Cozy Studio
3.0 star property
Craigleith
8.8 out of 10, Excellent, (11 reviews)
"Everything is nice"
Canada
Claudia
The price is AU$245
includes taxes & fees
4 Nov - 5 Nov
Ski In Ski Out Cozy Studio
A ski resort with multiple buildings, a ski slope, and a clear sky.

13. Blue Mtn 1 Bedroom with Mountain View

Blue Mtn 1 Bedroom with Mountain View
4.0 star property
Craigleith
9.2 out of 10, Wonderful, (9 reviews)
"The place was very clean and felt like your own home Close to all amenities Price was reasonable excellent place to relax and get away from Toronto busy life"
Canada
Marcello
The price is AU$291
includes taxes & fees
13 Oct - 14 Oct
Blue Mtn 1 Bedroom with Mountain View
A ski resort with multiple buildings, a ski slope, and a clear sky.

14. Rustic Mountainside Chalet

Rustic Mountainside Chalet
3.5 star property
Craigleith
9.2 out of 10, Wonderful, (5 reviews)
"Inside the unit everything was great. It was clean and well appointed with a well equipped kitchen. The outside deck area is moldy and needs some tlc. The unit we stayed in faced trees and was very quiet, but a bit dark. All in all, it was a pleasant place to stay for a few days to explore the area."
Canada
Ulrike
The price is AU$258
includes taxes & fees
2 Nov - 3 Nov
Rustic Mountainside Chalet
A snow-covered village with traditional wooden buildings, a ski lift, and a mountain backdrop.

15. Slopeside Loft at North Creek Resort

Slopeside Loft at North Creek Resort
4.0 star property
Craigleith
8.0 out of 10, Very good, (4 reviews)
"The property was great because it had 2 nice bathrooms. I was very disappointed that the patio was very worn and had no chairs so we couldn’t sit outside at night."
Canada
Peggy
The price is AU$320
includes taxes & fees
8 Nov - 9 Nov
Slopeside Loft at North Creek Resort
A ski resort with multiple buildings, a ski slope, and a clear sky.

16. Cozy Studio Loft with 2 Bath

Cozy Studio Loft with 2 Bath
4.0 star property
Craigleith
10.0 out of 10, Exceptional, (4 reviews)
"This was our 2nd time staying at the resort. Love the place. Will be staying again next year."
Canada
Dipti
The price is AU$349
includes taxes & fees
21 Oct - 22 Oct
Cozy Studio Loft with 2 Bath
A swimming pool with a modern building in the background.

17. Updated Blue Mountain studio North Creek

Updated Blue Mountain studio North Creek
3.0 star property
Craigleith
8.6 out of 10, Excellent, (4 reviews)
"We had a really nice stay at Blue Mountain. The location was great, just a few minutes’ drive from the Village, and there was plenty to do, especially with kids. The room was clean and comfortable, and the whole area had a fun, relaxed atmosphere. We really enjoyed all the activities and had a great time exploring the Village. Everything was close and convenient. Overall, it was a very enjoyable stay and a great little getaway. We’d definitely consider coming back!"
Canada
Louis
The price is AU$260
includes taxes & fees
26 Oct - 27 Oct
Updated Blue Mountain studio North Creek
A ski resort with multiple buildings, a ski slope, and a clear sky.

18. Hillside BLUE MTN family Loft

Hillside BLUE MTN family Loft
3.5 star property
Craigleith
7.8 out of 10, Good, (8 reviews)
"Nice view and pretty much everything you need for family trip"
Canada
Talwinder
The price is AU$350
includes taxes & fees
8 Nov - 9 Nov
Hillside BLUE MTN family Loft
A ski resort with multiple buildings, a ski slope, and a clear sky.

19. Gorgeous Loft in Heart of Blue Mountain

Gorgeous Loft in Heart of Blue Mountain
2.5 star property
Craigleith
9.8 out of 10, Exceptional, (7 reviews)
"It was a nice property close to the villages and beach!"
Canada
Paula
The price is AU$350
includes taxes & fees
13 Oct - 14 Oct
Gorgeous Loft in Heart of Blue Mountain
A ski resort with multiple buildings, a ski slope, and a clear sky.

20. Loft with a View of Blue

Loft with a View of Blue
4.0 star property
Craigleith
9.0 out of 10, Wonderful, (13 reviews)
"The pool was awesome, warm and very quiet."
Canada
Emile
The price is AU$339
includes taxes & fees
12 Oct - 13 Oct
Loft with a View of Blue
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

Midland Inn & Suites

Midland Inn & Suites

10/10 Excellent
"Clean rooms"
Monica 1-night trip
Posted 5 hours ago
Midland Inn & Suites

Find out more about Simcoe County

Everything you need to know about Simcoe County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Simcoe County holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Simcoe County holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simcoe County holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Simcoe County holiday rentals we have chosen for you start as low as AU$238 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 holiday 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 holiday.

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.