A marina with modern buildings, calm water, and a clear blue sky.

Simcoe County Vacation Rentals

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Top Cities in Simcoe County

A historic brick building with green shutters and a sign for 'Arcade'.
Vacation RentalsVacation Rentals

Collingwood

Collingwood

Our top choices for Simcoe County vacation rentals

A modern kitchen with a large window, built-in appliances, and a central island.

1. Downtown Collingwood Condos

Downtown Collingwood Condos
3.0 star property
Collingwood
9.0 out of 10, Wonderful, (45 reviews)
"This is a very cozy place!"
Canada
Zhaoqi
The price is CA $134
CA $310 total
includes taxes & fees
Nov 17 - Nov 18
Downtown Collingwood Condos
An indoor swimming pool with a wooden ceiling, large windows, and seating areas with potted plants.

2. Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room

Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
Oro Medonte
9.8 out of 10, Exceptional, (11 reviews)
"Fantastic stay. We had great service from the host and enjoyed the design. It's easy to see that a lot of effort was put into the decor. We felt very at home and would definitely stay there again."
Canada
Travis
The price is CA $136
CA $351 total
includes taxes & fees
Nov 9 - Nov 10
Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
A modern living room with a TV, a round coffee table, a sofa, and a view of a cityscape through large windows.

3. Stunning 1BR w Pool ~ Free Parking & Self Check-In

Stunning 1BR w Pool ~ Free Parking & Self Check-In
Innisfil
10.0 out of 10, Exceptional, (5 reviews)
"Although our stay was short, we had a wonderful experience. The host was excellent at communicating and made everything easy and seamless. The place was very clean, comfortable, and easily accessible. We really enjoyed our stay and would definitely love to come back!"
Canada
lisa
The price is CA $145
CA $278 total
includes taxes & fees
Nov 8 - Nov 9
Stunning 1BR w Pool ~ Free Parking & Self Check-In
A large indoor swimming pool with a high ceiling and a second level balcony overlooking the pool.

4. Lux Studio in Horseshoe Valley

Lux Studio in Horseshoe Valley
Oro
8.8 out of 10, Excellent, (5 reviews)
"Quiet location Pool was close by Community bbq Trails nearby Nice little apartment"
Canada
Sam
Lux Studio in Horseshoe Valley
Exterior

5. Sassafras Oasis Sleeps 14 - All Season Retreat Near Barrie

Sassafras Oasis Sleeps 14 - All Season Retreat Near Barrie
2.0 star property
Springwater
The price is CA $264
CA $546 total
includes taxes & fees
Nov 8 - Nov 9
Sassafras Oasis Sleeps 14 - All Season Retreat Near Barrie
A modern hotel with a rooftop pool and outdoor seating area.

6. Upscale Spa Getaway w/ Private Sauna

Upscale Spa Getaway w/ Private Sauna
Innisfil
The price is CA $179
CA $368 total
includes taxes & fees
Nov 8 - Nov 9
Upscale Spa Getaway w/ Private Sauna
A pool area with a hot tub and seating under a covered roof.

7. Cozy 1-Bedroom Romantic Retreat with full Kitchen

Cozy 1-Bedroom Romantic Retreat with full Kitchen
Oro-Medonte
10.0 out of 10, Exceptional, (1 review)
"What a wonderful place to stay! The hose was so welcoming from the first communication and throughout the trip. The property was exactly as described but maybe even nicer in person than the pictures. The condo was super spacious with loads of room in the main room plus the bedroom. And the bathroom! Wow! Definitely spa-like with a seperate tub and shower. Treasure is comfortable to hang out on. Instructions inside for pool and wifi were clear. The bed was super comfy! And the black out curtains...
United States
Rayissa N.
The price is CA $88
CA $207 total
includes taxes & fees
Nov 11 - Nov 12
Cozy 1-Bedroom Romantic Retreat with full Kitchen
A large indoor swimming pool with a high ceiling and a second-story balcony overlooking the pool.

8. Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing

Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing
Shanty Bay
8.8 out of 10, Excellent, (3 reviews)
"Excellent place to stay while enjoying the Valley."
United States
Amy R.
Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing
A modern living room with a wooden dining table, a sofa, and a television.

9. Bright 2 Bedroom Entire Basement Apartment

Bright 2 Bedroom Entire Basement Apartment
Angus
9.0 out of 10, Wonderful, (14 reviews)
"Our stay was great! The host was responsive and very nice! Would highly recommend!"
Canada
Julie
The price is CA $109
CA $293 total
includes taxes & fees
Nov 17 - Nov 18
Bright 2 Bedroom Entire Basement Apartment
A stone staircase leading up to a red building surrounded by trees.

10. Fiddlers Green at Evergreen Resort Wasaga Beach

Fiddlers Green at Evergreen Resort Wasaga Beach
Wasaga Beach
10.0 out of 10, Exceptional, (1 review)
"Jennifer provided exceptional customer service! What an incredible location and experience! We’ll be back!"
Canada
Patricia
Fiddlers Green at Evergreen Resort Wasaga Beach
A glass table with a bottle of champagne and two glasses, set against a backdrop of a cityscape and string lights.

11. Fire & Ice Spa w/ Private Sauna!

Fire & Ice Spa w/ Private Sauna!
Innisfil
10.0 out of 10, Exceptional, (13 reviews)
"Great views in a warm, fire-lit setting—perfect spot for a night out."
Canada
Craig
The price is CA $189
CA $397 total
includes taxes & fees
Nov 8 - Nov 9
Fire & Ice Spa w/ Private Sauna!
A dining area with a round table, four chairs, a potted plant, and a mirror on the wall.

12. FRIDAY HARBOUR CHIC WATERFRONT GETAWAY

FRIDAY HARBOUR CHIC WATERFRONT GETAWAY
Innisfil
9.6 out of 10, Exceptional, (7 reviews)
"Cozy space, large washroom, kitchen, perfect location!"
Canada
Elias
The price is CA $252
CA $306 total
includes taxes & fees
Nov 8 - Nov 9
FRIDAY HARBOUR CHIC WATERFRONT GETAWAY
Exterior

13. Friday Harbour Resort 2 Bedroom Pool Lake Simcoe

Friday Harbour Resort 2 Bedroom Pool Lake Simcoe
Innisfil
9.4 out of 10, Exceptional, (13 reviews)
"Check-in was easy, the apartment was clean and well equipped. Would stay again."
Canada
Albert M.
The price is CA $90
CA $258 total
includes taxes & fees
Nov 8 - Nov 9
Friday Harbour Resort 2 Bedroom Pool Lake Simcoe
A balcony with a sofa, a table with a fire feature, and string lights.

14. Oasis Spa w/ Private Sauna!

Oasis Spa w/ Private Sauna!
Innisfil
10.0 out of 10, Exceptional, (1 review)
"The Oasis Spa Getaway was a fantastic two night stay for my partner and I. The property was clean, modern and cozy! The unit had everything a couple needs for their stay including a sauna within the unit and a beautiful balcony. The host Michelle provided exceptional hospitality and was easy to connect with when needed. The location is great and only a short walk to the boardwalk and a quick two minute drive to the Nest golf course. The building’s pool was easy to access, quiet, and relaxing....
Canada
Matthew K.
The price is CA $170
CA $358 total
includes taxes & fees
Nov 8 - Nov 9
Oasis Spa w/ Private Sauna!
A pool with lounge chairs and a view of the ocean.

15. Beachy Daze in Wasaga Beach

Beachy Daze in Wasaga Beach
Wasaga Beach
Beachy Daze in Wasaga Beach
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a table and chairs.

16. BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE UNIT # 12

BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE UNIT # 12
Wasaga Beach
9.6 out of 10, Exceptional, (43 reviews)
"It was a wonderful stay, couldnt ask for a more relaxing/beautiful spot to spend the long weekend!"
United States
Alejandro G.
The price is CA $200
CA $505 total
includes taxes & fees
Nov 8 - Nov 9
BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE UNIT # 12
A hotel room with two beds, a large window with curtains, a ceiling fan, and a painting on the wall.

17. Spacious Resort Studio in Collingwood - 9 Min from Blue Mountain!

Spacious Resort Studio in Collingwood - 9 Min from Blue Mountain!
Collingwood
9.2 out of 10, Wonderful, (32 reviews)
"Place wqs great"
United States
miguel c.
The price is CA $156
CA $263 total
includes taxes & fees
Nov 8 - Nov 9
Spacious Resort Studio in Collingwood - 9 Min from Blue Mountain!
A cozy living room with a brown sofa, a coffee table, and a TV. There's a kitchen area with a fridge and a sink in the background.

18. Crazy Farm C-Can Chalet

Crazy Farm C-Can Chalet
Innisfil
8.8 out of 10, Excellent, (6 reviews)
"Hospitality was on key. Enjoyed our stay"
Canada
Hannah
The price is CA $112
CA $146 total
includes taxes & fees
Nov 24 - Nov 25
Crazy Farm C-Can Chalet
A wooden cabin with a front door, a wooden staircase, and a blue umbrella.

19. Traditional Tiny Wood Cottage #7 Camping style Cottages 5 minutes to the beach!

Traditional Tiny Wood Cottage #7 Camping style Cottages 5 minutes to the beach!
Wasaga Beach
8.6 out of 10, Excellent, (4 reviews)
"The cabin is at an ideal location and is close to the beach and other local attractions. The cabins are in a gated area and only the front gate it left unlocked overnight so it felt very safe and ideal for little kids and dogs. One of the hosts l, Tristan was so helpful and recommend a few places to check out in the area."
United States
Raz Q.
The price is CA $230
CA $329 total
includes taxes & fees
Nov 8 - Nov 9
Traditional Tiny Wood Cottage #7 Camping style Cottages 5 minutes to the beach!
A night scene with a fire feature, a bottle of champagne, and a starry sky visible through a glass enclosure.

20. Luxury Beach Spa w/ Private Sauna!

Luxury Beach Spa w/ Private Sauna!
Innisfil
9.8 out of 10, Exceptional, (7 reviews)
"We just wanted to get out of town and enjoy some peaceful and relaxing time away, and that’s exactly what we got. "
Canada
Dragisa
The price is CA $207
CA $435 total
includes taxes & fees
Nov 8 - Nov 9
Luxury Beach Spa w/ Private Sauna!
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

Living Stone Golf Resort

Living Stone Golf Resort

10/10 Excellent
"Amazing experience, close to all of shops and very peaceful stay."
Jasha 1-night trip
Posted 3 hours ago
Living Stone Golf Resort

Find out more about Simcoe County

Everything you need to know about Simcoe County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Simcoe County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Simcoe County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Simcoe County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Simcoe County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simcoe County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Simcoe County vacation rentals we have selected for you start as low as CA $278 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Simcoe County rentals

At Expedia, we put the best Simcoe County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Simcoe County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Simcoe County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Simcoe County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.