Simcoe County Holiday Rentals

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Top cities in Simcoe County

A scenic view of a hilly landscape with a dirt path leading to a viewpoint overlooking a coastal town and the ocean.
Vacation Rentals

Collingwood

Collingwood

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

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, (45 reviews)
"This is a very cozy place!"
Canada
Zhaoqi
The price is NZ$396
includes taxes & fees
17 Nov - 18 Nov
Downtown Collingwood Condos
A beachside setting with two chairs and a colorful umbrella, surrounded by trees and a view of the water.

2. Lake View Loft Studio type

Lake View Loft Studio type
Severn
8.6 out of 10, Excellent, (9 reviews)
"Stayed only 2 days . Very clean Loft . Beautiful view. Every thing went perfectly."
United States
Tom E.
The price is NZ$397
includes taxes & fees
10 Nov - 11 Nov
Lake View Loft Studio type
A modern living room with a TV, a round coffee table, a sofa, and a view of a cityscape through large windows.

3. 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, (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!"
Canada
lisa
The price is NZ$364
includes taxes & fees
10 Nov - 11 Nov
Stunning 1BR w Pool ~ Free Parking & Self Check-In
A modern hotel with a rooftop pool and outdoor seating area.

4. Upscale Spa Getaway w/ Private Sauna

Upscale Spa Getaway w/ Private Sauna
Innisfil
The price is NZ$464
includes taxes & fees
10 Nov - 11 Nov
Upscale Spa Getaway w/ Private Sauna
An indoor swimming pool with a wooden ceiling, large windows, and seating areas with potted plants.

5. Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room

Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
Oro 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."
Canada
Travis
The price is NZ$436
includes taxes & fees
15 Nov - 16 Nov
Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
A glass table with a bottle of champagne and two glasses, set against a backdrop of a cityscape and string lights.

6. 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
The price is NZ$501
includes taxes & fees
10 Nov - 11 Nov
Fire & Ice Spa w/ Private Sauna!
A balcony with a sofa, a table with a fire feature, and string lights.

7. 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....
Canada
Matthew K.
The price is NZ$450
includes taxes & fees
10 Nov - 11 Nov
Oasis Spa w/ Private Sauna!
A hotel room with two beds, a large window with curtains, a ceiling fan, and a painting on the wall.

8. 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"
United States
miguel c.
The price is NZ$336
includes taxes & fees
10 Nov - 11 Nov
Spacious Resort Studio in Collingwood - 9 Min from Blue Mountain!
Exterior

9. Sassafras Oasis Sleeps 14 - All Season Retreat Near Barrie

Sassafras Oasis Sleeps 14 - All Season Retreat Near Barrie
2.0 star property
Springwater
The price is NZ$696
includes taxes & fees
10 Nov - 11 Nov
Sassafras Oasis Sleeps 14 - All Season Retreat Near Barrie
A wooden deck with chairs and tables overlooking a lake, a flag, and a gazebo.

10. 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.
The price is NZ$225
includes taxes & fees
10 Nov - 11 Nov
Lakeview private suite with kitchen (Twin or King)
A modern kitchen with a central island, wooden staircase, and a dining area with white chairs.

11. Vacation Inn Townhomes

Vacation Inn Townhomes
4.0 star property
Collingwood
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!!!"
Canada
Madushi
The price is NZ$594
includes taxes & fees
10 Nov - 11 Nov
Vacation Inn Townhomes
A wooden building with a thatched roof entrance, a number '3' sign, and a Samsung air conditioning unit.

12. Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!

Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!
Wasaga Beach
8.0 out of 10, Very good, (4 reviews)
"Clean friendly easy check in and out all around great experience should recommend"
Canada
Jenna
The price is NZ$336
includes taxes & fees
10 Nov - 11 Nov
Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!
A dining area with a round table, four chairs, a potted plant, and a mirror on the wall.

13. FRIDAY HARBOUR CHIC WATERFRONT GETAWAY

FRIDAY HARBOUR CHIC WATERFRONT GETAWAY
Innisfil
9.6 out of 10, Exceptional, (7 reviews)
"Cozy space, large washroom, kitchen, perfect location!"
Canada
Elias
The price is NZ$388
includes taxes & fees
10 Nov - 11 Nov
FRIDAY HARBOUR CHIC WATERFRONT GETAWAY
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a table and chairs.

14. BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE UNIT # 12

BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE UNIT # 12
Wasaga Beach
9.6 out of 10, Exceptional, (43 reviews)
"It was a wonderful stay, couldnt ask for a more relaxing/beautiful spot to spend the long weekend!"
United States
Alejandro G.
The price is NZ$636
includes taxes & fees
10 Nov - 11 Nov
BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE UNIT # 12
A lakeside property with a wooden dock, lounge chairs, and a modern building with a glass facade.

15. Waterfront Stay | Lake Simcoe | 3BR Escape

Waterfront Stay | Lake Simcoe | 3BR Escape
Innisfil
The price is NZ$665
includes taxes & fees
12 Nov - 13 Nov
Waterfront Stay | Lake Simcoe | 3BR Escape
A deck with a table and chairs, a Coors Light branded umbrella, and a view of a lake.

16. Hidden Gem!!!

Hidden Gem!!!
Wasaga Beach
8.2 out of 10, Very good, (24 reviews)
"We enjoyed our getaway"
Canada
Katie M.
The price is NZ$722
includes taxes & fees
10 Nov - 11 Nov
Hidden Gem!!!
Exterior

17. Friday Harbour Resort 2 Bedroom Pool Lake Simcoe

Friday Harbour Resort 2 Bedroom Pool Lake Simcoe
Innisfil
9.4 out of 10, Exceptional, (14 reviews)
"Check-in was easy, the apartment was clean and well equipped. Would stay again."
Canada
Albert M.
The price is NZ$328
includes taxes & fees
10 Nov - 11 Nov
Friday Harbour Resort 2 Bedroom Pool Lake Simcoe
A cozy living room with a brown sofa, a coffee table, and a TV. There's a kitchen area with a fridge and a sink in the background.

18. Crazy Farm C-Can Chalet

Crazy Farm C-Can Chalet
Innisfil
8.8 out of 10, Excellent, (6 reviews)
"Hospitality was on key. Enjoyed our stay"
Canada
Hannah
The price is NZ$186
includes taxes & fees
24 Nov - 25 Nov
Crazy Farm C-Can Chalet
A kitchen with white cabinets, a stainless steel stove, and a refrigerator.

19. Mount St Louis Cottage

Mount St Louis Cottage
Oro-Medonte
9.4 out of 10, Exceptional, (3 reviews)
"It was an amazing and fun stay! The home was perfect and the whole location itself was also peaceful. Definitely will book it again!"
United States
denise.
The price is NZ$562
includes taxes & fees
10 Nov - 11 Nov
Mount St Louis Cottage
A house with a front porch, a welcome sign, and a swan statue.

20. ARCA Cozy Cabin-Innisfil Beach

ARCA Cozy Cabin-Innisfil Beach
Innisfil
9.4 out of 10, Exceptional, (18 reviews)
"Great place to stay"
United States
Daisy G.
The price is NZ$459
includes taxes & fees
29 Nov - 30 Nov
ARCA Cozy Cabin-Innisfil Beach
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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Find holiday rentals that suit your style

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Top Simcoe County Hotel Reviews

A Holiday Inn Express & Suites building with a covered entrance, stone pillars, and a well-lit facade.
Holiday Inn Express & Suites Collingwood by IHG

Holiday Inn Express & Suites Collingwood by IHG

Holiday Inn Express & Suites Collingwood by IHG
Collingwood

10/10 Excellent

Lorraine was amazing!
Australia
Mia
Reviewed February 14, 2026
Holiday Inn Express & Suites Collingwood by IHG

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 favorite 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 depends 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 selected for you start as low as NZ$225 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.