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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

An aerial view of a resort with multiple swimming pools, outdoor seating areas, and a large building with a distinctive roof.

1. 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 4 - Oct 5
Total with taxes and fees
Lux Studio in Horseshoe Valley
A modern kitchen with a large window, built-in appliances, and a central island.

2. Downtown Collingwood Condos

Downtown Collingwood Condos
3.0 star property
Collingwood
9.0 out of 10, Wonderful, (39 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
$205 nightly
The price is $241
Oct 4 - Oct 5
Total with taxes and fees
Downtown Collingwood Condos
A modern hotel with a rooftop pool and outdoor seating area.

3. Upscale Spa Getaway w/ Private Sauna

Upscale Spa Getaway w/ Private Sauna
Innisfil
$258 nightly
The price is $280
Oct 4 - Oct 5
Total with taxes and fees
Upscale Spa Getaway w/ Private Sauna
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.

4. Crazy Farm C-Can Chalet

Crazy Farm C-Can Chalet
Innisfil
8.8 out of 10, Excellent, (6 reviews)
"Super cool rental, fun but also realistic and got the job done! Good location & felt safe! Would def stay again!"
Canada
Ashley
$97 nightly
The price is $109
Nov 3 - Nov 4
Total with taxes and fees
Crazy Farm C-Can Chalet
A modern kitchen with a central island, a dining area with a herringbone-patterned wall, and a staircase leading to an upper level.

5. 124 Hurontario Unit 2

124 Hurontario Unit 2
Collingwood
$254 nightly
The price is $288
Oct 4 - Oct 5
Total with taxes and fees
124 Hurontario Unit 2
An indoor swimming pool with clear glass walls, a separate hot tub area, and lounge chairs along the side.

6. 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.
$152 nightly
The price is $154
Oct 5 - Oct 6
Total with taxes and fees
Cozy 1-Bedroom Romantic Retreat with full Kitchen
A rustic cabin with a stone chimney, wooden exterior, and a seating area with Adirondack chairs.

7. 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 7 - Oct 8
Total with taxes and fees
Guest house close to Blue Mountain, Wasaga Beach and Collingwood!
A modern living room with a TV, a round coffee table, a sofa, and a view of a cityscape through large windows.

8. 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 $213
Oct 6 - Oct 7
Total with taxes and fees
Stunning 1BR w Pool ~ Free Parking & Self Check-In
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.
$135 nightly
The price is $153
Oct 12 - Oct 13
Total with taxes and fees
Spacious Resort Studio in Collingwood - 9 Min from Blue Mountain!
A spacious hallway with a neutral color scheme, a beige sofa, and a shower area with a glass door.

10. 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
$168 nightly
The price is $190
Oct 5 - Oct 6
Total with taxes and fees
Clean & Cozy Home Near Downtown
A glass table with a champagne bucket and glasses on a balcony with string lights.

11. 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 $292
Oct 4 - Oct 5
Total with taxes and fees
Fire & Ice Spa w/ Private Sauna!
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
10.0 out of 10, Exceptional, (2 reviews)
"Excellent place to stay while enjoying the Valley."
United States
Amy R.
$216 nightly
The price is $235
Oct 6 - Oct 7
Total with taxes and fees
Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing
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.
$194 nightly
The price is $220
Oct 4 - Oct 5
Total with taxes and fees
Bright 2 Bedroom Entire Basement Apartment
Beach

14. BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 5

BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 5
Wasaga Beach
9.6 out of 10, Exceptional, (40 reviews)
"Great little beach front cottage perfect for a family vacation! We had a great time with the kids and theyre asking to go back already!"
Canada
Hubert
$321 nightly
The price is $372
Oct 4 - Oct 5
Total with taxes and fees
BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 5
A marina at dusk with boats docked, waterfront buildings, and a calm water surface reflecting the lights.

15. 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 6 - Oct 7
Total with taxes and fees
Oasis Spa w/ Private Sauna!
A modern kitchen with a central island, wooden staircase, and a dining area with white chairs.

16. 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 4 - Oct 5
Total with taxes and fees
Vacation Inn Townhomes
A lakeside view with three lounge chairs, a small table, and a stone wall.

17. Lake View Loft Studio type

Lake View Loft Studio type
Severn
8.4 out of 10, Very good, (8 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
$196 nightly
The price is $221
Oct 27 - Oct 28
Total with taxes and fees
Lake View Loft Studio type
A swimming pool with a fenced deck area, surrounded by trees and a view of a lake.

18. 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.
$193 nightly
The price is $218
Oct 26 - Oct 27
Total with taxes and fees
Bonnie 2 Cottage/Resort/Orillia, Muskoka
A deck with two white lounge chairs and a red railing overlooking a lake.

19. Lakeside Private suite (Queen bed room)

Lakeside Private suite (Queen bed room)
Loretto
8.0 out of 10, Very good, (4 reviews)
"We really enjoyed our stay, the place was clean and comfortable. Thank you so much."
Canada
Michael W.
$104 nightly
The price is $117
Oct 5 - Oct 6
Total with taxes and fees
Lakeside Private suite (Queen bed room)
A marina with boats docked, a clear blue sky, and a view of buildings in the distance.

20. FRIDAY HARBOUR CHIC WATERFRONT GETAWAY

FRIDAY HARBOUR CHIC WATERFRONT GETAWAY
Innisfil
9.6 out of 10, Exceptional, (5 reviews)
"Cozy space, large washroom, kitchen, perfect location!"
Canada
Elias
$202 nightly
The price is $228
Oct 4 - Oct 5
Total with taxes and fees
FRIDAY HARBOUR CHIC WATERFRONT GETAWAY
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

Days Inn by Wyndham Orillia

Days Inn by Wyndham Orillia

10/10 Excellent
"Great staff with affordable room"
Keith 1-night trip
Posted 8 hours ago
Days Inn by Wyndham Orillia

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 $241 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.