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

Holiday Rentals in Simcoe County

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Top Cities in Simcoe County

Our top choices for Simcoe County holiday rentals

1. Jacuzzi Suite Relaxing Retreat

Jacuzzi Suite Relaxing Retreat
Shanty Bay
9.4 out of 10, Exceptional, (26 reviews)
"The host was very accommodating and the place was very nice and exactly as described! Check in was easy and nicely laid out. "
Canada
Amanda
The price is €162
includes taxes & fees
23 Aug - 24 Aug
Jacuzzi Suite Relaxing Retreat

2. Downtown Collingwood Condos

Downtown Collingwood Condos
3.0 star property
Collingwood
9.0 out of 10, Wonderful, (35 reviews)
"Very nicely designed and located property. Everything was as described and communication with the host was very prompt. It was equipped with everything we needed and all amenities were within walking distance. Would happily stay again."
Canada
Hugo
The price is €203
includes taxes & fees
1 Sept - 2 Sept
Downtown Collingwood Condos

3. Cozy Getaway with Resort Perks

Cozy Getaway with Resort Perks
Shanty Bay
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay! Elijah was a pleasure to work with, always answering my questions. The space is well equipped for cooking in and we were pleased with the cleanliness of the accomodations."
Canada
Denise C.
The price is €298
includes taxes & fees
23 Aug - 24 Aug
Cozy Getaway with Resort Perks

4. ARCA Cozy Cabin-Innisfil Beach

ARCA Cozy Cabin-Innisfil Beach
Innisfil
10.0 out of 10, Exceptional, (12 reviews)
"Great spot for families"
Canada
Lesa W.
The price is €278
includes taxes & fees
20 Aug - 21 Aug
ARCA Cozy Cabin-Innisfil Beach

5. 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 €269
includes taxes & fees
3 Sept - 4 Sept
Fire & Ice Spa w/ Private Sauna!

6. 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 €401
includes taxes & fees
31 Aug - 1 Sept
BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE UNIT # 12

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, (42 reviews)
"It was a lovely cottage that was perfect for our needs. The host, Lisa, was great at communicating with us answering all questions clearly and quickly. The kitchen was well stocked and the rooms, including the beds were very comfortable."
Canada
Cherie
The price is €232
includes taxes & fees
15 Sept - 16 Sept
Guest house close to Blue Mountain, Wasaga Beach and Collingwood!

8. 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, (1 review)
"It was nicely furnished and decorated. I loved soaking in the bath. The balcony looked out over the woods. It felt private and peaceful."
Canada
Carly
The price is €213
includes taxes & fees
4 Sept - 5 Sept
Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing

9. BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 1

BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 1
Wasaga Beach
9.6 out of 10, Exceptional, (18 reviews)
"Amazing cottage and host. We had a great family time! Thank you."
Canada
Aayush
The price is €372
includes taxes & fees
13 Sept - 14 Sept
BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 1

10. 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.
The price is €178
includes taxes & fees
30 Aug - 31 Aug
Cozy 1-Bedroom Romantic Retreat with full Kitchen

11. The 1883 Century Hotel Suite

The 1883 Century Hotel Suite
Collingwood
9.8 out of 10, Exceptional, (41 reviews)
"Clean and nicely renovated property with great central location downtown Collingwood."
Canada
Robert
The price is €173
includes taxes & fees
18 Aug - 19 Aug
The 1883 Century Hotel Suite

12. 4-Bed Country Club Haven with Pool, BBQs, and More

4-Bed Country Club Haven with Pool, BBQs, and More
Oro
9.0 out of 10, Wonderful, (8 reviews)
"We stayed for 4 nights with our 3 children and had a great experience! Close to the ski hills and grocery store. Kids enjoyed the pool and games room. The room itself had everything we needed."
United States
Melissa
The price is €394
includes taxes & fees
31 Aug - 1 Sept
4-Bed Country Club Haven with Pool, BBQs, and More

13. Luxury Beach Spa w/ Private Sauna!

Luxury Beach Spa w/ Private Sauna!
Innisfil
9.8 out of 10, Exceptional, (7 reviews)
"We just wanted to get out of town and enjoy some peaceful and relaxing time away, and that’s exactly what we got. "
Canada
Dragisa
The price is €307
includes taxes & fees
7 Sept - 8 Sept
Luxury Beach Spa w/ Private Sauna!

14. 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 €322
includes taxes & fees
2 Sept - 3 Sept
Vacation Inn Townhomes

15. FRIDAY HARBOUR WATERFRONT CHIC GETAWAY

FRIDAY HARBOUR WATERFRONT CHIC GETAWAY
Innisfil
10.0 out of 10, Exceptional, (3 reviews)
"Cozy space, large washroom, kitchen, perfect location!"
Canada
Elias
The price is €207
includes taxes & fees
2 Sept - 3 Sept
FRIDAY HARBOUR WATERFRONT CHIC GETAWAY

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

Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
Oro Medonte
9.6 out of 10, Exceptional, (8 reviews)
"It was a beautiful place. The beds were very comfortable. It had everything we needed as well. "
United States
Allison G.
The price is €267
includes taxes & fees
9 Sept - 10 Sept
Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room

17. 124 Hurontario Unit 1

124 Hurontario Unit 1
Collingwood
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful place in a great location! Would definitely stay again!!"
Canada
Jo-Anne
The price is €259
includes taxes & fees
13 Sept - 14 Sept
124 Hurontario Unit 1

18. 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.
The price is €157
includes taxes & fees
19 Aug - 20 Aug
Spacious Resort Studio in Collingwood - 9 Min from Blue Mountain!

19. 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
The price is €183
includes taxes & fees
16 Sept - 17 Sept
Stunning 1BR w Pool ~ Free Parking & Self Check-In

20. House in Wasaga only 18 min away from Blue Mountain! 5 min away from the beach!

House in Wasaga only 18 min away from Blue Mountain! 5 min away from the beach!
Wasaga Beach
10.0 out of 10, Exceptional, (7 reviews)
"Nice location and clean, refreshing, and relaxing atmosphere. Very spacious, even with many people. Very responsive and helpful owner."
Canada
Jamie F.
The price is €376
includes taxes & fees
19 Aug - 20 Aug
House in Wasaga only 18 min away from Blue Mountain! 5 min away from the 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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Top Simcoe County Hotel Reviews

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Holiday Homes in Simcoe County

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