Simcoe County Holiday Rentals from €213: Search Short-Term Rentals

A hillside with autumn foliage, a rocky cliff, and a field of wildflowers.

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Top Cities in Simcoe County

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

Our top choices for Simcoe County holiday 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

Oro

Sam

includes taxes & fees

4 Oct - 5 Oct

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

2. Downtown Collingwood Condos

Collingwood

Benny

includes taxes & fees

4 Oct - 5 Oct

A modern hotel with a rooftop pool and outdoor seating area.

3. Upscale Spa Getaway w/ Private Sauna

Innisfil

includes taxes & fees

2 Oct - 3 Oct

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

Innisfil

Hannah

includes taxes & fees

1 Nov - 2 Nov

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

Collingwood

includes taxes & fees

4 Oct - 5 Oct

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

Oro-Medonte

"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...

Rayissa N.

includes taxes & fees

5 Oct - 6 Oct

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!

Nottawa

Christopher

includes taxes & fees

6 Oct - 7 Oct

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

Innisfil

Jennifer

includes taxes & fees

5 Oct - 6 Oct

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!

Collingwood

miguel c.

includes taxes & fees

2 Oct - 3 Oct

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

New Tecumseth

Suzanne

includes taxes & fees

5 Oct - 6 Oct

A glass table with a champagne bucket and glasses on a balcony with string lights.

11. Fire & Ice Spa w/ Private Sauna!

Innisfil

Craig

includes taxes & fees

4 Oct - 5 Oct

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

Shanty Bay

Carly

includes taxes & fees

6 Oct - 7 Oct

A modern living room with a wooden dining table, a sofa, and a television.

13. Bright 2 Bedroom Entire Basement Apartment

Angus

Adriano A.

includes taxes & fees

4 Oct - 5 Oct

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

Wasaga Beach

Hubert

includes taxes & fees

4 Oct - 5 Oct

A marina at dusk with boats docked, waterfront buildings, and a calm water surface reflecting the lights.

15. Oasis Spa w/ Private Sauna!

Innisfil

"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....

Matthew K.

includes taxes & fees

7 Oct - 8 Oct

A modern kitchen with a central island, wooden staircase, and a dining area with white chairs.

16. Vacation Inn Townhomes

Collingwood

Linda

includes taxes & fees

4 Oct - 5 Oct

A lakeside view with three lounge chairs, a small table, and a stone wall.

17. Lake View Loft Studio type

Severn

Jason

includes taxes & fees

22 Oct - 23 Oct

A swimming pool with a fenced deck area, surrounded by trees and a view of a lake.

18. Bonnie 2 Cottage/Resort/Orillia, Muskoka

Washago

Luis F.

includes taxes & fees

21 Oct - 22 Oct

A deck with two white lounge chairs and a red railing overlooking a lake.

19. Lakeside Private suite (Queen bed room)

Loretto

Michael W.

includes taxes & fees

4 Oct - 5 Oct

A marina with boats docked, a clear blue sky, and a view of buildings in the distance.

20. FRIDAY HARBOUR CHIC WATERFRONT GETAWAY

Innisfil

Elias

includes taxes & fees

4 Oct - 5 Oct

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Top Simcoe County Hotel Reviews

Days Inn by Wyndham Orillia

10/10 Excellent

"Affordable room. Friendly staff"

Midland Inn & Suites

10/10 Excellent

"We really enjoyed the breakfast each morning. The addition of hot chocolate is our only suggestion. The rubber tub mat is greatly appreciated as we age and are not as steady on our feet. Next time, we may request a main floor room as the stairs aren't quite as easy as they used to be. Age marches on. he addition of hot chocolate"

Living Water Resort and Spa

10/10 Excellent

"We really enjoyed this resort! We loved the massages from the Spa and found the Aquapath to be truly one of a kind. The property sits on a serene section of the bay which was very picturesque with the fall foliage. Admittedly we anticipated the tennis court to be a hard court so we didn’t end up playing for long. Every other amenity in the property is amazing! We will be coming back."

Find out more about Simcoe County

Holiday Homes in Simcoe County

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Look no further and take a look at our great range of rental properties in Simcoe County!

Holiday Rentals in Simcoe County

Change your mind

Treat yourself

Be picky

Top Cities in Simcoe County

Collingwood

Our top choices for Simcoe County holiday rentals

1. Lux Studio in Horseshoe Valley

2. Downtown Collingwood Condos

3. Upscale Spa Getaway w/ Private Sauna

4. Crazy Farm C-Can Chalet

5. 124 Hurontario Unit 2

6. Cozy 1-Bedroom Romantic Retreat with full Kitchen

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

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

9. Spacious Resort Studio in Collingwood - 9 Min from Blue Mountain!

10. Clean & Cozy Home Near Downtown

11. Fire & Ice Spa w/ Private Sauna!

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

13. Bright 2 Bedroom Entire Basement Apartment

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

15. Oasis Spa w/ Private Sauna!

16. Vacation Inn Townhomes

17. Lake View Loft Studio type

18. Bonnie 2 Cottage/Resort/Orillia, Muskoka

19. Lakeside Private suite (Queen bed room)

20. FRIDAY HARBOUR CHIC WATERFRONT GETAWAY

Find holiday rentals that suit your style

Top Simcoe County Hotel Reviews

Days Inn by Wyndham Orillia

Find out more about Simcoe County

Holiday Homes in Simcoe County