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

Vacation Rentals in Simcoe County

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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, (43 reviews)
"This is a very cozy place!"
Canada
Zhaoqi
$189 nightly
The price is $222
Oct 28 - Oct 29
Total with taxes and fees
Downtown Collingwood Condos
A large indoor swimming pool with a high ceiling and a second level balcony overlooking the pool.

2. Lux Studio in Horseshoe Valley

Lux Studio in Horseshoe Valley
Oro
8.8 out of 10, Excellent, (5 reviews)
"Quiet location Pool was close by Community bbq Trails nearby Nice little apartment"
Canada
Sam
$154 nightly
The price is $167
Oct 28 - Oct 29
Total with taxes and fees
Lux Studio in Horseshoe Valley
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, (4 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
$192 nightly
The price is $217
Oct 27 - Oct 28
Total with taxes and fees
Stunning 1BR w Pool ~ Free Parking & Self Check-In
An outdoor patio with round tables and chairs, a pool, and a house in the background.

4. 2 bedroom townhome with view of the mountain

2 bedroom townhome with view of the mountain
Collingwood
9.6 out of 10, Exceptional, (11 reviews)
"Cute and cozy pet friendly getaway from the city"
Canada
Gabrielle S.
$278 nightly
The price is $316
Nov 1 - Nov 2
Total with taxes and fees
2 bedroom townhome with view of the mountain
A large indoor swimming pool with a high ceiling and a second-story balcony overlooking the pool.

5. 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.
$220 nightly
The price is $239
Oct 27 - Oct 28
Total with taxes and fees
Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing
A stone staircase leading up to a red building surrounded by trees.

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
$232 nightly
The price is $249
Oct 27 - Oct 28
Total with taxes and fees
Fiddlers Green at Evergreen Resort Wasaga Beach
A beachside setting with two chairs and a colorful umbrella, surrounded by trees and a view of the water.

7. 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
$200 nightly
The price is $226
Oct 27 - Oct 28
Total with taxes and fees
Lake View Loft Studio type
A pool area with a hot tub and seating under a covered roof.

8. 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.
$154 nightly
The price is $157
Oct 29 - Oct 30
Total with taxes and fees
Cozy 1-Bedroom Romantic Retreat with full Kitchen
A modern hotel with a rooftop pool and outdoor seating area.

9. Upscale Spa Getaway w/ Private Sauna

Upscale Spa Getaway w/ Private Sauna
Innisfil
$250 nightly
The price is $270
Oct 27 - Oct 28
Total with taxes and fees
Upscale Spa Getaway w/ Private Sauna
A bedroom with two beds, a window with blinds, a bedside lamp, a coat rack, and a framed picture on the wall.

10. 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.
$197 nightly
The price is $222
Oct 28 - Oct 29
Total with taxes and fees
Bonnie 2 Cottage/Resort/Orillia, Muskoka
A modern kitchen with a central island, a dining area with a herringbone-patterned wall, and a staircase leading to an upper level.

11. 124 Hurontario Unit 2

124 Hurontario Unit 2
Collingwood
$253 nightly
The price is $287
Oct 27 - Oct 28
Total with taxes and fees
124 Hurontario Unit 2
A balcony with a sofa, a table with a fire feature, and string lights.

12. 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.
$250 nightly
The price is $270
Oct 27 - Oct 28
Total with taxes and fees
Oasis Spa w/ Private Sauna!
A modern living room with a wooden dining table, a sofa, and a television.

13. 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.
$190 nightly
The price is $215
Nov 2 - Nov 3
Total with taxes and fees
Bright 2 Bedroom Entire Basement Apartment
A wooden deck with chairs and tables overlooking a lake, a flag, and a gazebo.

14. 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.
$127 nightly
The price is $144
Oct 27 - Oct 28
Total with taxes and fees
Lakeview private suite with kitchen (Twin or King)
A hotel room with two beds, a large window with curtains, a ceiling fan, and a painting on the wall.

15. 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.
$174 nightly
The price is $197
Oct 27 - Oct 28
Total with taxes and fees
Spacious Resort Studio in Collingwood - 9 Min from Blue Mountain!
A swimming pool with a diving board, surrounded by trees and a building with a sign.

16. Dockhouse at Evergreen Resort in Wasaga Beach

Dockhouse at Evergreen Resort in Wasaga Beach
Wasaga Beach
10.0 out of 10, Exceptional, (2 reviews)
"Very nice and clean property. Disappointed about the pool not being heated."
United States
Rita R.
$245 nightly
The price is $265
Oct 27 - Oct 28
Total with taxes and fees
Dockhouse at Evergreen Resort in Wasaga Beach
A swimming pool with a surrounding deck, a covered seating area, and a view of the ocean.

17. Wasaga Daze - Unit B

Wasaga Daze - Unit B
Wasaga Beach
$212 nightly
The price is $228
Oct 27 - Oct 28
Total with taxes and fees
Wasaga Daze - Unit B
A glass table with a bottle of champagne and two glasses, set against a backdrop of a cityscape and 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
$270 nightly
The price is $291
Oct 29 - Oct 30
Total with taxes and fees
Fire & Ice Spa w/ Private Sauna!
A spacious hallway with a neutral color scheme, a beige sofa, and a shower area with a glass door.

19. 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
$176 nightly
The price is $199
Nov 19 - Nov 20
Total with taxes and fees
Clean & Cozy Home Near Downtown
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a table and chairs.

20. 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.
$326 nightly
The price is $378
Nov 1 - Nov 2
Total with taxes and fees
BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE UNIT # 12
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

The Dorchester Hotel

The Dorchester Hotel

10/10 Excellent
"Our third visit to The Dorchester Hotel and we love it more every time."
Tony 2-night trip
Posted 11 hours ago
The Dorchester Hotel

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 $167 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?


Vacation rentals in Simcoe County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Simcoe County vacation rentals to suit everyone. 


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.