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

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

Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
Victoria Harbour
8.2 out of 10, Very Good, (16 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 1,178 total
includes taxes & fees
7 Apr - 8 Apr
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage

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

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

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

Lake Simcoe Waterfront Retreat | Expansive Private Grounds · Ideal for Groups

Lake Simcoe Waterfront Retreat | Expansive Private Grounds · Ideal for Groups
Gilford
9.8 out of 10, Exceptional, (13 reviews)
"Terrific place for our group of 12 golfers. Lots of space and every amenity we could hope for."
Canada
Chris C.
The price is AED 2,059
AED 4,214 total
includes taxes & fees
25 Mar - 26 Mar
Lake Simcoe Waterfront Retreat | Expansive Private Grounds · Ideal for Groups

5 Beds Luxury Retreat at Wasaga Beach

5 Beds Luxury Retreat at Wasaga Beach
Wasaga Beach
8.6 out of 10, Excellent, (15 reviews)
"It was such a wonderfully place!!! We enjoyed so much this lovely house for one night when we skiied at the blue mountain. The owner responded quickly whenever i ask some little stuffs even though everything was ready! Thanks!"
Canada
Min
The price is AED 723
AED 1,730 total
includes taxes & fees
25 Mar - 26 Mar
5 Beds Luxury Retreat at Wasaga Beach

Driftwood on 6th in Historic Downtown Collingwood/Pet Friendly

Driftwood on 6th in Historic Downtown Collingwood/Pet Friendly
Collingwood
9.8 out of 10, Exceptional, (34 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

Spacious 6-bdrm luxury, modern house with lake view in cottage country, Ontario

Spacious 6-bdrm luxury, modern house with lake view in cottage country, Ontario
Victoria Harbour
9.8 out of 10, Exceptional, (8 reviews)
"Excellent place to stay. Well equipped. "
Canada
Fabricio Z.
Spacious 6-bdrm luxury, modern house with lake view in cottage country, Ontario

Georgian Bay Cottage- Hot Tub/Sauna/Trail/Run/Bike/Swim//Marina!

Georgian Bay Cottage- Hot Tub/Sauna/Trail/Run/Bike/Swim//Marina!
Waubaushene
9.6 out of 10, Exceptional, (18 reviews)
"Amazing, hot tub, sauna, and everything was very clean and enjoyable"
Canada
Kevin B.
Georgian Bay Cottage- Hot Tub/Sauna/Trail/Run/Bike/Swim//Marina!

Four Season Waterfront Cottage Over-the-Water view

Four Season Waterfront Cottage Over-the-Water view
Orillia
9.4 out of 10, Exceptional, (11 reviews)
"The place is perfect for reunion. Close to orillia "
Canada
sean y.
Four Season Waterfront Cottage Over-the-Water view

Modern Luxury Retreat with Stunning Views & Open Concept Design

Modern Luxury Retreat with Stunning Views & Open Concept Design
severn
10.0 out of 10, Exceptional, (3 reviews)
"Amazing stay for a girls getaway weekend!"
Canada
Angue
The price is AED 434
AED 1,231 total
includes taxes & fees
25 Mar - 26 Mar
Modern Luxury Retreat with Stunning Views & Open Concept Design

VILLA UPPER & LOWER SPECIAL RATES SLEEPS 15, VERY CLOSE TO BEACH ACCESS,

VILLA UPPER & LOWER SPECIAL RATES SLEEPS 15, VERY CLOSE TO BEACH ACCESS,
Wasaga Beach
9.8 out of 10, Exceptional, (7 reviews)
"Lots of space for our family. Loved the 2 kitchens! Perfect for cooking Xmas dinner. Close to all ammenities. Close to Bluemountain. Unfortunately the hills were closed for most of our stay because of the rain. But we enjoyed walks on the beach and trails thru the park which is only a 5 min walk down the street. The house was clean and well maintained. We all had a great time! Loved it!"
Canada
Beth G.
VILLA UPPER & LOWER SPECIAL RATES SLEEPS 15, VERY CLOSE TO BEACH ACCESS,

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

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

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

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

Sun, Sand and S'mores-The Great Escape STRTT-2026-071

Sun, Sand and S'mores-The Great Escape STRTT-2026-071
Penetanguishene
10.0 out of 10, Exceptional, (13 reviews)
"Great family space. Quiet but close to the beach and lots of great outdoor activities. Perfect for family fun. "
Canada
Amy and Kevin W.
Sun, Sand and S'mores-The Great Escape STRTT-2026-071

4 Beds New paradise, wasaga beach

4 Beds New paradise, wasaga beach
Wasaga Beach
10.0 out of 10, Exceptional, (4 reviews)
"Home was very clean and open concept, it was a great location, 12 mins from the beach"
Canada
Valentina
The price is AED 648
AED 1,700 total
includes taxes & fees
6 Apr - 7 Apr
4 Beds New paradise, wasaga beach

Beach front- Wasaga Beach/AC/BBQ/ Near Blue Mountain

Beach front- Wasaga Beach/AC/BBQ/ Near Blue Mountain
Wasaga Beach
9.0 out of 10, Wonderful, (18 reviews)
"Very cleanConvenience near tims, restaurant's. Location is fantastic. Right on the beach with a pool and volleyball court. Everything you need provided and a bbq. Quiet area. Would recommend and or stay again. "
Canada
Ilona G.
Beach front- Wasaga Beach/AC/BBQ/ Near Blue Mountain

Entire Bungalow in Wasaga Beach ⛱️

Entire Bungalow in Wasaga Beach ⛱️
Wasaga Beach
9.6 out of 10, Exceptional, (4 reviews)
"We were a group of 11 friends who stayed here for a couple of days while we skied in Collingwood. The house was clean and exactly as described. Plenty of beds for our group. Communication with the host was really good and he allowed us to check in early. "
Canada
Caden T.
Entire Bungalow in Wasaga Beach ⛱️

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, (15 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!

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 385
AED 1,180 total
includes taxes & fees
19 Apr - 20 Apr
2 bedroom townhome Collingwood
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