Holiday Homes in Simcoe County

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Top Cities in Simcoe County

Featured Holiday Homes in Simcoe County

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

9.4 out of 10, Exceptional, (24)
"We had a great time and the home was perfect for us"
Vacation Escape ~Sauna~Fireplace ~BBQ~ Outdoor Fire-pit ~Ping pong

House with 4.5 bedrooms,10 Acres of forest creek and trails, lots of parking

House with 4.5 bedrooms,10 Acres of forest creek and trails, lots of parking

Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage

10.0 out of 10, Exceptional, (1)
"We stayed here to compete in Timber Tour at Mount St. Louis . 3 athletes, coach and parent. 5 bedrooms, 2 bathrooms was ideal and easily could have had more stay with us. Will book next season if we come back for same Timber Tour "
The price is AU$517
includes taxes & fees
18 Feb - 19 Feb
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage

Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!

9.4 out of 10, Exceptional, (71)
"Owner was very friendly and communicative. Place was very clean. Excellent lake view. Has all amenities. Grocery and other stores within 15min drive. Excellent for weekend retreat. "
Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!

Horseshoe Valley Suites - The Glade

4.0 star property
9.8 out of 10, Exceptional, (6)
"Great place to stay"
Horseshoe Valley Suites - The Glade

The Oake Room - Modern Convenience

9.8 out of 10, Exceptional, (17)
"The location was very safe, the instructions were clear for access into the apartment.Everything was very clean, nice decor. Attention to detail of possible needs. Supplied with tea/coffee/water/snacks.Wonderful overall."
The price is AU$226
includes taxes & fees
18 Feb - 19 Feb
The Oake Room - Modern Convenience

Heart of Wasaga Beach•Waterfront•BBQ•Patio•KingBed

8.0 out of 10, Very good, (1)
"This property is beautiful, very clean, well maintained and had a wonderful view and location. We really enjoyed our stay. Only thing that was a bit disappointing is the amenities; the listing states capacity of 12 ppl but the place is not equipped for that many. There were only 8 of us and we couldn’t find linens for the pull up sofa, also the kitchen had very few glasses for beverages, and no wine glasses or coffee mugs…etc. Nevertheless we did enjoy our stay and would recommend the place but...
Heart of Wasaga Beach•Waterfront•BBQ•Patio•KingBed

4 Bedroom Lakefront Townhouse Cottage

8.8 out of 10, Excellent, (3)
"Awesome natural surroundings. Cottage vibes and a lot of space for activities. Not giving 5 stars only because of power outage in the town which not really was anyone’s fault but we ended up wasting 4 hours of our trip with no water or electricity. "
4 Bedroom Lakefront Townhouse Cottage

Luxury Georgian Bay gem, heated pool! Hot tub, close to trails & lake

10.0 out of 10, Exceptional, (1)
"We wished we could have stayed longer!!Grandchildren, loved the pool. Lots of room for entertaining. Close to walking trails and the Bay."
Luxury Georgian Bay gem, heated pool! Hot tub, close to trails & lake

Kickback in Beautiful tranquil centrally located condo

10.0 out of 10, Exceptional, (2)
"Excellent stay in the heart of collingwood close to all the fun .Girlfriend getaway of hiking shopping and dancing with the most hospitable people Recommended highly "
The price is AU$494
includes taxes & fees
3 Mar - 4 Mar
Kickback in Beautiful tranquil centrally located condo

Cozy home with all the amenities you need, just 1min walk from a beautiful beach

10.0 out of 10, Exceptional, (18)
"The necessities, that you could need, for you stay, bedding, utensils, plates, cooking implements, and the basic necessities were readily available. The location was as advertised, and the beach was great. The whole Family. had an enjoyable stay"
Cozy home with all the amenities you need, just 1min walk from a beautiful beach

Large Corner Townhome @Carriage!

10.0 out of 10, Exceptional, (2)
"I will definitely reserve again with Jason. Spacious and clean one bedroom condo with connecting studio condo. I’m hoping that the queen mattresses will be replaced before my next visit. They were hard as rock."
The price is AU$407
includes taxes & fees
3 Mar - 4 Mar
Large Corner Townhome @Carriage!

Welcome to Lake House by Lis, where stunning lake views and serene sunsets await

9.6 out of 10, Exceptional, (7)
"We were in town for a hockey tournament and this home was in a great location. A nice little getaway but still close to the rinks. If you like to ice fish this is also the perfect spot! The attention to details did not go unnoticed. Lis was a great host and always available if we had questions. We would highly recommend this home. "
Welcome to Lake House by Lis, where stunning lake views and serene sunsets await

5 Beds Luxury Retreat at Wasaga Beach

9.0 out of 10, Wonderful, (6)
"Love the place"
The price is AU$517
includes taxes & fees
23 Feb - 24 Feb
5 Beds Luxury Retreat at Wasaga Beach

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

HOT TUB-Natural paradise, timber frame, sauna, close to Casino and ski hill.

10.0 out of 10, Exceptional, (78)
"Fires, saunas, hot tub, eating, board games, puzzles and relaxation. We love our weekend getaway at the cabin in the woods! Thanks so much, Pat! "
HOT TUB-Natural paradise, timber frame, sauna, close to Casino and ski hill.

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

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

9.0 out of 10, Wonderful, (7)
"We had a great stay and enjoyed our time in Horseshoe Valley.The unit was spacious and overall very pleasant.A couple of suggestions to make things even better:- there was no toaster and we like our toast in the morning!-also no ice cube trays so we couldn't make our drinks cold the way we like them- we also had to wrestle a little with a couple of drawers in the kitchen that were difficult to open and close - and not all the lamps seemed to be workingHaving said that, the place suited our needs...
A lovely two-bedroom condo in Carriage Hills sleeps 8 persons

6-Bedroom Modern Escape in Horseshoe-Pool+Hot tub

6-Bedroom Modern Escape in Horseshoe-Pool+Hot tub

Beautiful unique and exceptional house.

Beautiful unique and exceptional house.
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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