Vacation Homes in Simcoe County

Compare and save
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Top Cities in Simcoe County

Our top choices for Simcoe County vacation homes

Modern Home by Georgian Bay w/ hot tub. Pet friendly!!

Modern Home by Georgian Bay w/ hot tub. Pet friendly!!
Midland
9.6 out of 10, Exceptional, (9 reviews)
"Very comfortable and good location "
Canada
Barbara M.
Modern Home by Georgian Bay w/ hot tub. Pet friendly!!

Horseshoe Valley Suites - The Glade

Horseshoe Valley Suites - The Glade
4.0 star property
Oro-Medonte
9.0 out of 10, Wonderful, (9 reviews)
"Great place to stay"
Canada
Elizabeth
Horseshoe Valley Suites - The Glade

Driftwood on 6th in Historic Downtown Collingwood/Pet Friendly

Driftwood on 6th in Historic Downtown Collingwood/Pet Friendly
Collingwood
10.0 out of 10, Exceptional, (32 reviews)
"Great location, walkable to down town. Quick access to Blue Mountain. Wonderful property. "
Canada
Mary-Ellen M.
Driftwood on 6th in Historic Downtown Collingwood/Pet Friendly

Cozy beach bungalow with deck, BBQ, high-speed Wi-Fi & steps to the shoreline

Cozy beach bungalow with deck, BBQ, high-speed Wi-Fi & steps to the shoreline
Wasaga Beach
8.0 out of 10, Very Good, (1 review)
The price is AED 246
AED 763 total
includes taxes & fees
10 Feb - 11 Feb
Cozy beach bungalow with deck, BBQ, high-speed Wi-Fi & steps to the shoreline

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

Welcome to Lake House by Lis, where stunning lake views and serene sunsets await
Innisfil
9.6 out of 10, Exceptional, (15 reviews)
"Place has been newly renovated, very clean and comfortable. Was the perfect spot for our group of 6, would recommend!"
Canada
Joanne H.
Welcome to Lake House by Lis, where stunning lake views and serene sunsets await

Beach1. com - Beach House # 4 - Beachfront Wasanga Beach

Beach1. com - Beach House # 4 - Beachfront Wasanga Beach
Wasaga Beach
7.6 out of 10, Good, (4 reviews)
"Overall super. We have a few comments : 1- almost no water pressure in the kitchen sink, this must be fixed, really an irritant after a week. 2- all the sofas smelled very strong of wet dog. We had to use fabreez on the fabric twice to get it to a tolerable level. 3- on arrival we felt sand on all surfaces on the ground level (table, counters…), the cleaning crew must be carefull about this. 4- the upper level TV in the family room is not fonctionnal. Like I said, overall super, just a few...
Canada
Julie G.
Beach1. com - Beach House # 4 - Beachfront Wasanga Beach

Clean & Cozy Home Near Downtown

Clean & Cozy Home Near Downtown
New Tecumseth
10.0 out of 10, Exceptional, (3 reviews)
"Very cozy stay for a weekend hockey tournament."
Canada
Suzanne
The price is AED 321
AED 733 total
includes taxes & fees
9 Mar - 10 Mar
Clean & Cozy Home Near Downtown

Private Boyne River Cottage- steps to great fishing

Private Boyne River Cottage- steps to great fishing
New Tecumseth
6.0 out of 10, (1 review)
"It would have been more welcoming if there would have been coffee, tea and water available so you don’t have to go looking for a place to buy it. The deck area was not clean, the tables and chairs were dirty. The second bedroom should have a more comfortable bed. There was a very musty smell throughout the whole house. The house was nice and clean. If everything above is looked after I would stay there again if I came back to Alliston."
Canada
Olga V.
Private Boyne River Cottage- steps to great fishing

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

Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
Victoria Harbour
8.6 out of 10, Excellent, (14 reviews)
"This rental was very affordable with lots of beds. We enjoyed our stay and had plenty of room for a larger group."
United States
Chris L.
The price is AED 395
AED 1,185 total
includes taxes & fees
9 Feb - 10 Feb
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage

The Alpine - Central Collingwood Condo

The Alpine - Central Collingwood Condo
2.5 star property
Collingwood
10.0 out of 10, Exceptional, (1 review)
"Property was very clean! Washer + dryer and dishwasher were very useful, and owners were quick to bring us a new lightbulb when one of them went out."
Canada
guangwei
The Alpine - Central Collingwood Condo

2 bedroom townhome Collingwood

2 bedroom townhome Collingwood
Collingwood
9.6 out of 10, Exceptional, (7 reviews)
"Excellent "
Canada
Christine D.
The price is AED 392
AED 1,189 total
includes taxes & fees
18 Feb - 19 Feb
2 bedroom townhome Collingwood

Cozy Blue Mountain Escape Perfect for Relaxation & Adventure

Cozy Blue Mountain Escape Perfect for Relaxation & Adventure
Collingwood
The price is AED 459
AED 1,278 total
includes taxes & fees
9 Feb - 10 Feb
Cozy Blue Mountain Escape Perfect for Relaxation & Adventure

Brand new waterfront LUXE lake house for a beautiful week/end away!

Brand new waterfront LUXE lake house for a beautiful week/end away!
Hawkestone
9.8 out of 10, Exceptional, (6 reviews)
"We enjoyed our stay in this cottage. We were 6 adults and the house was neat and comfortable for all. "
United States
Raed A.
Brand new waterfront LUXE lake house for a beautiful week/end away!

Casa Di Nonna

Casa Di Nonna
2.0 star property
Wasaga Beach
8.0 out of 10, Very Good, (1 review)
Casa Di Nonna

Cozy Beachside Getaway – Steps from Balm Beach!

Cozy Beachside Getaway – Steps from Balm Beach!
Tiny
10.0 out of 10, Exceptional, (1 review)
"Exactly how described in listing, clean & everything we needed to enjoy our stay. Excellent communication from owners. No complaints!"
Canada
Laura S.
The price is AED 378
AED 1,078 total
includes taxes & fees
9 Mar - 10 Mar
Cozy Beachside Getaway – Steps from Balm Beach!

Wasaga Beach year round cottage! 3 minute walk to the longest fresh water Beach.

Wasaga Beach year round cottage! 3 minute walk to the longest fresh water Beach.
Wasaga Beach
8.8 out of 10, Excellent, (8 reviews)
"Jenny's beach flat was a wonderful time. Plenty of games to play, a short walk to the beach and a clean and charming house."
Canada
Courtney L.
Wasaga Beach year round cottage! 3 minute walk to the longest fresh water Beach.

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

6-Bedroom Modern Escape in Horseshoe-Pool+Hot tub
Coldwater
10.0 out of 10, Exceptional, (1 review)
"Chantal has a beautiful home that accommodated our family of 5 adults and 2 young children for a wedding at Braestone Golf and County Club. The location was ideal as the club grounds could be seen from her home. Chantal was an excellent communicator and responded promptly with any of my queries. The house is beautiful with large spacious bedrooms and a well equipped kitchen. She is indeed a super host!"
Canada
barbara m.
6-Bedroom Modern Escape in Horseshoe-Pool+Hot tub

Vacation Home on Simcoe lake

Vacation Home on Simcoe lake
Innisfil
2.0 out of 10, (1 review)
"The owner had removed the property and we apparently booked with some kind of zombie account. VRBO had not validated the listing but kept communicating everything was good to go. VRBO did book our party of nine hotel rooms. These were over a half hour from the property and no where near the beach. We had no facility to prepare the food we had brought and were forced to eat at restaurants the whole weekend. VRBO did ensure the accomodation was financially neutral, but it was still, overall, a...
Canada
Dave S.
Vacation Home on Simcoe lake

The Captains Lake House

The Captains Lake House
Orillia
10.0 out of 10, Exceptional, (3 reviews)
"We had a wonderful few days in our hosts beautiful home. Amazing sunrise to start the day and a winter wonderland to spend our family Christmas all together. The home was welcoming right from the start with all our expectations being exceeded. Thank you so much."
Canada
Ralph N.
The price is AED 1,350
AED 2,658 total
includes taxes & fees
7 Feb - 8 Feb
The Captains Lake House

Beautiful 3-Bdrm Cottage close to Ski Resorts w/ Hot Tub, Game Room, & more!

Beautiful 3-Bdrm Cottage close to Ski Resorts w/ Hot Tub, Game Room, & more!
Tiny
9.6 out of 10, Exceptional, (12 reviews)
"Everything was great - Hot tub and fire pit was a bonus …bed was comfy…restful and tranquil- we walked everyday (5min) to the beach to watch the sun set and the nature was lovely- it was a quiet beautiful peaceful Thanksgiving- couple time was perfect! Only one restaurant in town (5min walk) but food was excellent. "
Canada
Mike
Beautiful 3-Bdrm Cottage close to Ski Resorts w/ Hot Tub, Game Room, & more!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Simcoe County Hotel Reviews