Holiday Homes in Simcoe County

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Top Cities in Simcoe County

Featured Holiday Homes in Simcoe County

The Oake Room - Modern Convenience

10.0 out of 10, Exceptional, (11)
"We had a great stay here. The unit was very clean and was a beautiful space. Would recommend!"
The price is AU$224
includes taxes & fees
1 Dec - 2 Dec
The Oake Room - Modern Convenience

The 1883 Century Flat- Collingwood, ON

9.8 out of 10, Exceptional, (21)
"The home showed beautifully like something you would see in a magazine. Everything was well thought out so had all the necessities you need and more. And a lovely private outside area. The location was perfect a block away from downtown and a few blocks from the bay. Park right in front and forget driving until you leave."
The price is AU$285
includes taxes & fees
27 Nov - 28 Nov
The 1883 Century Flat- Collingwood, ON

Horseshoe Valley Suites - The Glade

4.0 star property
9.6 out of 10, Exceptional, (4)
"Great place to stay"
Horseshoe Valley Suites - The Glade

Friday Harbour Prime Location - Luxurious Lakeside Escape

10.0 out of 10, Exceptional, (2)
"We stayed at this condo for a weekend get away with another couple. The condo is beautifully decorated and is fully stocked for your stay. It is located close to the stores and restaurants at Friday Harbour and is just a quick stroll away. The view of the marina is stunning - we enjoyed the patio heater and propane fire pit and cozy blankets and were able to stay out on the patio well into the evening despite being mid October. The owners responded quickly to all of my questions and even...
Friday Harbour Prime Location - Luxurious Lakeside Escape

Vacation Escape ~Sauna~Fireplace ~BBQ~ Outdoor Fire-pit ~Ping pong

9.2 out of 10, Wonderful, (19)
"The property manager was exceptionally helpful. Thanks so much."
Vacation Escape ~Sauna~Fireplace ~BBQ~ Outdoor Fire-pit ~Ping pong

Where Luxury Retreat meets Convenience!

5.6 out of 10, (7)
"utilities was not as required and also the barbecue was not working over all the stay was nice and my friends and family really like"
The price is AU$1,577
includes taxes & fees
30 Nov - 1 Dec
Where Luxury Retreat meets Convenience!

Cozy Lakeside Cabin with Private Balcony.

8.4 out of 10, Very good, (6)
"Love the staging style of decor and layout. Comfortable and roomy. Beach with paddle boards and kayaks. Excellent communication with friendly host."
The price is AU$409
includes taxes & fees
26 Nov - 27 Nov
Cozy Lakeside Cabin with Private Balcony.

Spacious and modern townhome in Collingwood

9.6 out of 10, Exceptional, (10)
"We had a wonderful getaway! The accommodation was clean and very nice. It was close to amenities, downtown Collingwood, and short drive to Wasaga beach. The host was very responsive to inquiries and always responded quickly. We can't wait to stay again!"
Spacious and modern townhome in Collingwood

Luxurious Lake front Island Twnhome Friday Harbour

8.8 out of 10, Excellent, (8)
"Great place for a family reunion. Everyone under one roof, and close to the FH amenities. "
Luxurious Lake front Island Twnhome Friday Harbour

Pet-Friendly Nostigic Cabin with access to private lakefront

10.0 out of 10, Exceptional, (4)
"We had a wonderful getaway with our small family of four for Thanksgiving weekend. Though some may feel the space is small, it was perfect for our needs, and a very warm and welcoming step up from the tent camping that we would have done otherwise. It is a shared building with other rented spaces (I believe there are 5 in total) but not an issue at all, as each unit has its own private entrance. The back yard area includes a fire pit for campfires and there is a gravel path down to the private...
The price is AU$274
includes taxes & fees
24 Nov - 25 Nov
Pet-Friendly Nostigic Cabin with access to private lakefront

Lakeside Escape 3-Bedroom Bungalow with a Hot Tub

6.0 out of 10, (2)
"Not a lakeside property, it's a bungalow house with no lake access. Property did not look like the pictures posted on the site at all. The house itself was nice in the inside with 3 small bedrooms. Did not stay there i cancelled as soon as i got thdre and realized it was not even close to what i was renting"
Lakeside Escape 3-Bedroom Bungalow with a Hot Tub

Spa Golf Bike Ski Refresh

10.0 out of 10, Exceptional, (1)
"The condo was just the ticket for an overnight stay after a Celebration of Life event. The pictures do not due it justice...bigger and brighter than anticipated. The hotel like details were a nice touch! Very happy with our choice! Ann"
The price is AU$390
includes taxes & fees
1 Dec - 2 Dec
Spa Golf Bike Ski Refresh

Party Paradise Retreat -cozy stay 5 mins away from wasaga beach!

7.0 out of 10, Good, (2)
"The house was great, had lots of room and great decorating. Love that the bedrooms had space for your things alongside the bed. I would say this place is bare bones though, no dressers for your clothes, no side tables or lamps in all of the rooms. The beds were very cheap and the mattresses were uncomfortable (you could feel the springs). There were linens and towels provided but I’m not sure how deep a clean this place gets in between guests (found hair in the shower, hair on the toilet, floors...
The price is AU$492
includes taxes & fees
8 Dec - 9 Dec
Party Paradise Retreat -cozy stay 5 mins away from wasaga beach!

Executive Villa - Year Round Swim Spa & Game Room

10.0 out of 10, Exceptional, (2)
"It was an excellent experience!"
Executive Villa - Year Round Swim Spa & Game Room

Spa Ski Apres Repeat

Spa Ski Apres Repeat

A lovely two-bedroom condo in Carriage Hills sleeps 8 persons

9.0 out of 10, Wonderful, (6)
"The host of the condo was absolutely fabulous to communicate with. She was always quick to reply to any questions or concerns, and prompt to message each evening and morning to ensure no issues arose during our stay. The condo in proximity to our parking space was perfect to unload, even at night the area was impressively well lite. I appreciated the perfect escape with a friend to relax in nature and enjoy the impressive living space, while recharging with a big music festival weekend! I would...
A lovely two-bedroom condo in Carriage Hills sleeps 8 persons

5 Beds Luxury Retreat at Wasaga Beach

10.0 out of 10, Exceptional, (2)
"The stay was calm and quiet "
5 Beds Luxury Retreat at Wasaga Beach

A gorgeous Coach House located in Downtown Collingwood close to Blue Mountain

10.0 out of 10, Exceptional, (17)
"Have stayed her a few times. Just love the space. It's clean and comfortable with a good kitchen and supplies, etc. I especially like the location--close to downtown but not too close. Highly recommended. "
A gorgeous Coach House located in Downtown Collingwood close to Blue Mountain

Architectural open concept Country Home On sandy Lake

7.4 out of 10, Good, (3)
Architectural open concept Country Home On sandy Lake

Beautiful country escape 5 min. from beach

10.0 out of 10, Exceptional, (2)
"This place was perfect for our short weekend family trip away from the city! We brought our two dogs with us and we all enjoyed spending time in their space, especially their backyard. It was so well kept. Their pool was so much fun with the volleyball net, we were glad that it was still open during September! The place was also super close to a small beach down the rode and a 10 min drive from Innisfil Beach Park, I would definitely hope to stay at this place again."
Beautiful country escape 5 min. from 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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Beautiful view of the beach with palm trees

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