Vacation Homes in Simcoe County

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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)
"The host responded timely and the place was a perfect fit for what we were looking for."
Canada
Mya H.
The price is AED 396
AED 1,188 total
includes taxes & fees
10 May - 11 May
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

Game Room Getaway + Cozy Retreat Near Blue Mtn Ski Resort, Golf & Spa FREE Park

Game Room Getaway + Cozy Retreat Near Blue Mtn Ski Resort, Golf & Spa FREE Park
Collingwood
10.0 out of 10, Exceptional, (1 review)
"The house is spacious, clean and is a great option for a family or group. A garage for parking was nice during the cold, wet weather. Even had a ping pong table, air hockey and foosball table in the basement."
Canada
Heather
Game Room Getaway + Cozy Retreat Near Blue Mtn Ski Resort, Golf & Spa FREE Park

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

A lovely two-bedroom condo in Carriage Hills sleeps 8 persons
Oro
8.6 out of 10, Excellent, (14 reviews)
"Place was spacious and good for a group. Great location. In need of some repairs and missing some basic supplies. "
Canada
Lisa M.
A lovely two-bedroom condo in Carriage Hills sleeps 8 persons

Spacious 4 Bedroom House in Angus

Spacious 4 Bedroom House in Angus
Angus
9.6 out of 10, Exceptional, (5 reviews)
"Hassan was a fabulous host and the place was a great stay for our group! Would use again!"
Canada
Jesse
The price is AED 373
AED 965 total
includes taxes & fees
8 Jun - 9 Jun
Spacious 4 Bedroom House in Angus

6 Bedroom Large Family Home near Lake Simcoe & Innisfil Beach - Patio & BBQ

6 Bedroom Large Family Home near Lake Simcoe & Innisfil Beach - Patio & BBQ
Alcona
9.8 out of 10, Exceptional, (89 reviews)
"Excellent kitchen facilities, location & family-friendly space with separate bedrooms to give individual/couple space too.Thanks again!"
Canada
Kristi A.
6 Bedroom Large Family Home near Lake Simcoe & Innisfil Beach - Patio & BBQ

Wasaga Beach/ Blue Mountain Ski Hills/ Christmas village/ Lake Front/

Wasaga Beach/ Blue Mountain Ski Hills/ Christmas village/ Lake Front/
Wasaga Beach
9.8 out of 10, Exceptional, (30 reviews)
"Amenities were clean and well stocked. The beach was beautiful. The pool was nice.We will go again next year "
Canada
christine f.
Wasaga Beach/ Blue Mountain Ski Hills/ Christmas village/ Lake Front/

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, (5 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 AED 1,209
AED 2,185 total
includes taxes & fees
14 May - 15 May
House in Wasaga only 18 min away from Blue Mountain! 5 min away from the beach!

Four Season Waterfront Cottage Over-the-Water view

Four Season Waterfront Cottage Over-the-Water view
Orillia
9.4 out of 10, Exceptional, (13 reviews)
"Great place to stay highly recommend. "
United States
William R.
Four Season Waterfront Cottage Over-the-Water view

Vacation Inn Townhomes

Vacation Inn Townhomes
3.5 star property
Collingwood
9.6 out of 10, Exceptional, (4 reviews)
"This is great property and located in a beautiful area! It was nice and clean and we loved our stay! Highly recommend the place!!!"
Canada
Madushi
The price is AED 513
AED 1,250 total
includes taxes & fees
10 May - 11 May
Vacation Inn Townhomes

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, (37 reviews)
"Good location and nice details "
Canada
debbie c.
The price is AED 1,544
AED 2,601 total
includes taxes & fees
15 May - 16 May
Driftwood on 6th in Historic Downtown Collingwood/Pet Friendly

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,

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

Little Lake Escape | Waterfront 2 Bedroom Getaway

Little Lake Escape | Waterfront 2 Bedroom Getaway
Midland
10.0 out of 10, Exceptional, (1 review)
"I reserved this property for a two-night stay seeking a tranquil retreat, and it certainly met my expectations! The residence was impeccably maintained, and the panoramic views from the backyard were truly stunning. The firepit offered a comforting warmth, enhancing the experience of observing the sunset over the lake. The hosts provided all essential information for my stay, facilitating a seamless check-in process upon my arrival. Furthermore, their responsiveness to my inquiries was...
United States
T. J.
Little Lake Escape | Waterfront 2 Bedroom Getaway

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

Modern Lake Simcoe Waterfront Home

Modern Lake Simcoe Waterfront Home
Orillia
Modern Lake Simcoe Waterfront Home

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!

Farm House Oasis: Hot Tub, Pool, Horses sleeps 12

Farm House Oasis: Hot Tub, Pool, Horses sleeps 12
Minesing
9.6 out of 10, Exceptional, (5 reviews)
"Very enjoyable stay! "
Canada
Stefan A.
Farm House Oasis: Hot Tub, Pool, Horses sleeps 12

Luxurious Lake front Island Twnhome Friday Harbour

Luxurious Lake front Island Twnhome Friday Harbour
Innisfil
8.8 out of 10, Excellent, (10 reviews)
"We enjoyed our stay here during a major storm. The home was very welcoming and suited our needs . "
Canada
Barb
Luxurious Lake front Island Twnhome Friday Harbour

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

HOT TUB-Natural paradise, timber frame, sauna, close to Casino and ski hill.
Coldwater
10.0 out of 10, Exceptional, (92 reviews)
"4th year staying at the cabin in the woods for our annual girls’ trip. A lovely stay!"
Canada
Lindsay C.
HOT TUB-Natural paradise, timber frame, sauna, close to Casino and ski hill.
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