A hillside with autumn foliage, a rocky cliff, and a field of wildflowers.

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, (37 reviews)
"Very nicely designed and located property. Everything was as described and communication with the host was very prompt. It was equipped with everything we needed and all amenities were within walking distance. Would happily stay again."
Canada
Hugo
The price is CA $147
CA $326 total
includes taxes & fees
Sep 23 - Sep 24
Downtown Collingwood Condos
An aerial view of a resort with multiple swimming pools, outdoor seating areas, and a large building with a distinctive roof.

2. Lux Studio in Horseshoe Valley

Lux Studio in Horseshoe Valley
Oro
8.8 out of 10, Excellent, (3 reviews)
"Quiet location Pool was close by Community bbq Trails nearby Nice little apartment"
Canada
Sam
The price is CA $108
CA $218 total
includes taxes & fees
Sep 23 - Sep 24
Lux Studio in Horseshoe Valley
A modern hotel with a rooftop pool and outdoor seating area.

3. Upscale Spa Getaway w/ Private Sauna

Upscale Spa Getaway w/ Private Sauna
Innisfil
The price is CA $198
CA $410 total
includes taxes & fees
Sep 25 - Sep 26
Upscale Spa Getaway w/ Private Sauna
A modern living room with a TV, a round coffee table, a sofa, and a view of a cityscape through large windows.

4. 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, (3 reviews)
"This place was immaculate. Host was always super responsive. Had everything we needed. Highly recommend. We really enjoyed our stay."
Canada
Jennifer
The price is CA $145
CA $298 total
includes taxes & fees
Sep 23 - Sep 24
Stunning 1BR w Pool ~ Free Parking & Self Check-In
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.

5. Crazy Farm C-Can Chalet

Crazy Farm C-Can Chalet
Innisfil
8.4 out of 10, Very good, (5 reviews)
"Hospitality was on key. Enjoyed our stay"
Canada
Hannah
The price is CA $130
CA $179 total
includes taxes & fees
Sep 23 - Sep 24
Crazy Farm C-Can Chalet
A spacious hallway with a neutral color scheme, a beige sofa, and a shower area with a glass door.

6. Clean & Cozy Home Near Downtown

Clean & Cozy Home Near Downtown
New Tecumseth
8.4 out of 10, Very good, (6 reviews)
"Very cozy stay for a weekend hockey tournament."
Canada
Suzanne
The price is CA $114
CA $268 total
includes taxes & fees
Sep 23 - Sep 24
Clean & Cozy Home Near Downtown
A marina with boats docked, a clear blue sky, and a view of buildings in the distance.

7. FRIDAY HARBOUR CHIC WATERFRONT GETAWAY

FRIDAY HARBOUR CHIC WATERFRONT GETAWAY
Innisfil
9.6 out of 10, Exceptional, (5 reviews)
"Cozy space, large washroom, kitchen, perfect location!"
Canada
Elias
The price is CA $252
CA $321 total
includes taxes & fees
Sep 23 - Sep 24
FRIDAY HARBOUR CHIC WATERFRONT GETAWAY

8. Lovely & cozy private vacation home/Cottage 3 min. walk to Beach 2

Lovely & cozy private vacation home/Cottage 3 min. walk to Beach 2
Wasaga Beach
9.4 out of 10, Exceptional, (3 reviews)
"Good location, clean inside, but behind the building was much stink door because they had put some bags of old food garbage inside the garage!"
Canada
Anoush P.
The price is CA $199
CA $440 total
includes taxes & fees
Sep 23 - Sep 24
Lovely & cozy private vacation home/Cottage 3 min. walk to Beach 2
A wooden boardwalk through a natural area with dense vegetation and a clear sky.

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

Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
Victoria Harbour
8.4 out of 10, Very good, (27 reviews)
"The place has everything you need for comfortable stay with clean big rooms and supplies. It is an Old Place with spacious and ample rooms. Doors needs some greasing and it would also help to have some light in the yard for evening. Overall experience was great."
Canada
Akhila
The price is CA $148
CA $439 total
includes taxes & fees
Sep 23 - Sep 24
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
A glass table with a champagne bucket and glasses on a balcony with string lights.

10. 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 $198
CA $427 total
includes taxes & fees
Sep 23 - Sep 24
Fire & Ice Spa w/ Private Sauna!
An indoor swimming pool with clear glass walls, a separate hot tub area, and lounge chairs along the side.

11. 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 $81
CA $213 total
includes taxes & fees
Sep 24 - Sep 25
Cozy 1-Bedroom Romantic Retreat with full Kitchen
A resort with a large pool, outdoor seating, and a modern building with a glass facade.

12. Hillside Haven: Serene Studio Retreat for 4

Hillside Haven: Serene Studio Retreat for 4
Oro-Medonte
9.0 out of 10, Wonderful, (6 reviews)
"Clean room and had all amenities we were looking for!"
Canada
Roxanne
The price is CA $81
CA $198 total
includes taxes & fees
Sep 27 - Sep 28
Hillside Haven: Serene Studio Retreat for 4
A marina at dusk with boats docked, waterfront buildings, and a calm water surface reflecting the lights.

13. 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 $193
CA $402 total
includes taxes & fees
Sep 23 - Sep 24
Oasis Spa w/ Private Sauna!
An aerial view of a resort with multiple swimming pools, outdoor seating areas, and a large building with a distinctive roof.

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

Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing
Shanty Bay
10.0 out of 10, Exceptional, (1 review)
"It was nicely furnished and decorated. I loved soaking in the bath. The balcony looked out over the woods. It felt private and peaceful."
Canada
Carly
The price is CA $174
CA $330 total
includes taxes & fees
Sep 24 - Sep 25
Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing

15. BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 5

BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 5
Wasaga Beach
9.6 out of 10, Exceptional, (40 reviews)
"Great little beach front cottage perfect for a family vacation! We had a great time with the kids and theyre asking to go back already!"
Canada
Hubert
The price is CA $200
CA $528 total
includes taxes & fees
Sep 23 - Sep 24
BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 5
A modern kitchen with a central island, wooden staircase, and a dining area with white chairs.

16. Vacation Inn Townhomes

Vacation Inn Townhomes
4.0 star property
Collingwood
8.4 out of 10, Very good, (7 reviews)
"The property was very clean and exactly as described. It was centrally located to all amenities and attractions in the area. I would definitely stay here again. Excellent all around!"
Canada
Linda
The price is CA $156
CA $465 total
includes taxes & fees
Oct 5 - Oct 6
Vacation Inn Townhomes
A rustic cabin with a stone chimney, wooden exterior, and a seating area with Adirondack chairs.

17. Guest house close to Blue Mountain, Wasaga Beach and Collingwood!

Guest house close to Blue Mountain, Wasaga Beach and Collingwood!
Nottawa
10.0 out of 10, Exceptional, (46 reviews)
"Great place to stay!"
Canada
Christopher
The price is CA $180
CA $346 total
includes taxes & fees
Sep 27 - Sep 28
Guest house close to Blue Mountain, Wasaga Beach and Collingwood!

18. 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 $150
CA $344 total
includes taxes & fees
Sep 23 - Sep 24
Friday Harbour Resort 2 Bedroom Pool Lake Simcoe
A modern living room with a sofa, a TV, and large windows.

19. Brand New Luxury Modern Above Ground Suite Bond Head Retreat/Peaceful

Brand New Luxury Modern Above Ground Suite Bond Head Retreat/Peaceful
Bond head
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home and the host was very accommodating. One of the best places to stay in the area."
United States
A A.
The price is CA $151
CA $255 total
includes taxes & fees
Sep 29 - Sep 30
Brand New Luxury Modern Above Ground Suite Bond Head Retreat/Peaceful
A modern pool area with a clear blue pool, lounge chairs, and a covered seating area.

20. Friyay Harbour Retreat Condo

Friyay Harbour Retreat Condo
Innisfil
6.0 out of 10, (4 reviews)
"We used door dash so we didn’t need to cook. I would suggest new frying pans and stock paper supply’s for the days paid. We paid for 6 days, left the 5th day. I would think 6 rolls of Toilet paper would be nice and paper towels."
United States
Lori J.
The price is CA $135
CA $324 total
includes taxes & fees
Sep 23 - Sep 24
Friyay Harbour Retreat Condo
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

Quality Inn & Conference Centre

Quality Inn & Conference Centre

8/10 Good
"Staff was friendly and helpful. The breakfast was good . However the blankets on the bed weren’t very clean. Asked for new ones and was delivered right away tho. Would definitely go back."
Desirae 2-night trip
Posted 5 hours ago
Quality Inn & Conference Centre

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 $198 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.