Simcoe County Vacation Rentals

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Top Cities in Simcoe County

Collingwood which includes heritage architecture
Vacation RentalsVacation Rentals

Collingwood

Collingwood

Top Vacation Rentals in in Simcoe County

Waterfront Muskoka with Pool & Hot Tub
Fridge, microwave, oven, stovetop
Waterfront Muskoka with Pool & Hot Tub
9.6 out of 10, Exceptional, (17)
"Our stay at the cottage was fantastic. It was beautiful, filled with games for the kids, and offered canoeing on the lake. Jesse is very kind, welcoming and hospitable and let us stay longer than planned. We loved the peaceful, relaxing environment and cooking lunch over an open fire. Definitely recommended."
The price is CA $400
CA $711 total
includes taxes & fees
Jun 9 - Jun 10
Waterfront Muskoka with Pool & Hot Tub
Dock Life Beach 1 - Cottage 12, Riverview, 1 Bedroom, 3 min walk to Beach 1
Property grounds
Dock Life Beach 1 - Cottage 12, Riverview, 1 Bedroom, 3 min walk to Beach 1
9.4 out of 10, Exceptional, (6)
"We had an amazing stay here ! The place was extremely clean. Quite location & just a quick walk to the main beach. The staff was very friendly as well. Would highly recommend and will stay at this place again if ever I head back to wasaga."
The price is CA $140
CA $185 total
includes taxes & fees
Jun 11 - Jun 12
Dock Life Beach 1 - Cottage 12, Riverview, 1 Bedroom, 3 min walk to Beach 1
Exquisite Log Cabin Retreat- Perfect Couple’s Getaway! Tranquility at its best❤️
Fridge, microwave, oven, stovetop
Exquisite Log Cabin Retreat- Perfect Couple’s Getaway! Tranquility at its best❤️
10.0 out of 10, Exceptional, (257)
"Our stay was wonderful, the property better than advertised. So cozy and welcoming, nothing but peace and quiet. "
Exquisite Log Cabin Retreat- Perfect Couple’s Getaway! Tranquility at its best❤️
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The 1883 Century Flat- Collingwood, ON
Fridge, microwave, oven, stovetop
The 1883 Century Flat- Collingwood, ON
9.6 out of 10, Exceptional, (14)
"Our stay was short but it was perfect for our visit. Great location, though be warned it can be a little noisy with some loud cars, but nothing we weren’t already accustomed to. Would definitely stay again! "
The price is CA $109
CA $235 total
includes taxes & fees
Jun 12 - Jun 13
The 1883 Century Flat- Collingwood, ON
head River cottage , Kawartha Lakes
Smart TV, fireplace
head River cottage , Kawartha Lakes
9.4 out of 10, Exceptional, (41)
"This cottage was so beautiful and the neighbours were so friendly. "
head River cottage , Kawartha Lakes
COTTAGE # 6
Property grounds
COTTAGE # 6
9.2 out of 10, Wonderful, (30)
"Great location and short walk to the beach. Cozy cottage. Only negative was the ramp into cottage makes it a bit difficult to get items up. Would definitely recommend."
The price is CA $275
CA $611 total
includes taxes & fees
Jun 10 - Jun 11
COTTAGE # 6
Cottage tiny heaven.
Interior
Cottage tiny heaven.
9.4 out of 10, Exceptional, (12)
"We were a group of 14 extended family members who stayed here for 2 nights 3 days. Property was excellent, clean, and well stocked with everything you might need. We did have to use 2x of the provided air mattresses and pull-out sofa's to make enough beds for all of us - everyone was however very comfortable. The views from inside or on the deck are amazing, couldn't get enough of it! The rocky beach does make it a bit challenging to get in and out of the water especially for younger kids...
Cottage tiny heaven.
Margarita Vacation Get Away
Indoor pool, outdoor pool, open noon to 8:00 PM, lifeguards on site
Margarita Vacation Get Away
3.5 star property
9.4 out of 10, Exceptional, (3)
"Clean and cozy property. Great communication from owner. However, pictures showed a jetted tub, larger suite, and rear facing patio (which we later learned were for the larger suite next door also owned by the owners who were fabulous.) I would suggest separating the two property pictures to avoid future confusion. "
Margarita Vacation Get Away
Lovely Water Front Cottage- pool,firepit and amenities near by & access to water
Fridge, microwave, oven, stovetop
Lovely Water Front Cottage- pool,firepit and amenities near by & access to water
10.0 out of 10, Exceptional, (1)
"This property exceeded our expectations! My friends and I had a blast staying here.The place is spotless, just as pictured, and stocked with everything we needed. It's in a safe, gated area, conveniently located near various towns and attractions. Levon's recommendations for winter activities were a plus. We extended our stay because we loved it, and the Levon was incredibly accommodating. A fantastic experience!"
Lovely Water Front Cottage- pool,firepit and amenities near by & access to water
Horseshoe Valley Condos
Exterior
Horseshoe Valley Condos
3.5 star property
8.4 out of 10, Very good, (10)
"Great property- very clean and modern. Lovely countryside and very close to the Horseshoe Valley ski resort. Looking forward to visiting again in the summer. "
Horseshoe Valley Condos
Bed and Break fast home in Collingwood for 6 people
Property grounds
Bed and Break fast home in Collingwood for 6 people
9.8 out of 10, Exceptional, (6)
"We had a great stay at Devadasan’s place. The beds and couches were comfortable. We loved the breakfast offerings in the morning."
The price is CA $229
CA $295 total
includes taxes & fees
Jun 9 - Jun 10
Bed and Break fast home in Collingwood for 6 people
Muskoka - The Eagle's Nest
Smart TV, fireplace
Muskoka - The Eagle's Nest
9.8 out of 10, Exceptional, (31)
"The location is amazing, the pictures don’t do it justice. The locals were very nice and friendly members of my group had spoken to lots of people while on the provided boats. Henry was a great host and was very understanding and helpful with special requests with my group. Henry responded quickly and I have nothing negative to say about him or our experience as a whole. We made many great memories on our trip and we hope to visit again! 5 Star Experience!"
Muskoka - The Eagle's Nest
Dock Life Cottage 5 - Riverside, 1 Bedroom, Wasaga
Property grounds
Dock Life Cottage 5 - Riverside, 1 Bedroom, Wasaga
9.8 out of 10, Exceptional, (18)
"One of the most relaxing weekends I have had in a long time, from amazing people to beautiful views. I will definitely be returning."
Dock Life Cottage 5 - Riverside, 1 Bedroom, Wasaga
The Hidden Gem Near Casino Rama/Lake Couchiching
Fridge, microwave, oven, stovetop
The Hidden Gem Near Casino Rama/Lake Couchiching
10.0 out of 10, Exceptional, (24)
"We were a group of 6 adults who stayed here over the May long weekend and we could not be more pleased with the experience! The property was so beautiful and the location was a perfect escape. The cottage itself was immaculate and stocked with everything we could possibly need (even down to citronella candles and makeup wipes!) which made our stay super comfortable and convenient. The attention to detail in maintaining and preparing the cottage was evident, and it truly felt like a home away...
The Hidden Gem Near Casino Rama/Lake Couchiching
The Nordic - Central Collingwood Condo
Fridge, microwave, oven, stovetop
The Nordic - Central Collingwood Condo
8.4 out of 10, Very good, (8)
"It was just what we needed as our family was at the Spartan race. Very clean with enough space, it gave us the feel of being at home."
The price is CA $144
CA $377 total
includes taxes & fees
Jun 23 - Jun 24
The Nordic - Central Collingwood Condo
Paradise Suites - Peaceful Getaway
Exterior
Paradise Suites - Peaceful Getaway
10.0 out of 10, Exceptional, (3)
"We enjoyed this house very much. House was very clean and well furnished. I highly recommend this house."
The price is CA $750
CA $1,350 total
includes taxes & fees
Jun 9 - Jun 10
Paradise Suites - Peaceful Getaway
Modern Waterfront Home on Georgian Bay w/ Hot Tub!
Property grounds
Modern Waterfront Home on Georgian Bay w/ Hot Tub!
9.6 out of 10, Exceptional, (5)
"This fully renovated cottage is bright and spacious with a beautiful view of the lake from the kitchen / living room area. We loved sitting around the large kitchen island while we cooked together and enjoyed our family time. All four bedrooms boast luxurious beds and good temperature control, providing everyone a restful and comfortable sleep. The hot tub and games room provided a space to relax and have fun too. A multi-use trail is a 4min walk from the cottage. The house was spotless and so...
Modern Waterfront Home on Georgian Bay w/ Hot Tub!
The Oake Room - Modern Convenience
1 bedroom, iron/ironing board, free WiFi, bed sheets
The Oake Room - Modern Convenience
10.0 out of 10, Exceptional, (3)
"The Oake Room was such a perfect place for our stay in Alliston. Very, very clean and neat and had all the amenities that we needed. It was a cozy place to relax after a long day of meetings. Cozy doesn't mean small, the unit has ample space. Cozy means inviting. Sophie made sure that there was cream for the coffee, water and little snacks in case we needed to nibble on something. It's a great place to stay, Sophie made sure we were settled and comfortable. The location is convenient to get to....
The price is CA $120
CA $200 total
includes taxes & fees
Jun 9 - Jun 10
The Oake Room - Modern Convenience
Bright & Cozy Two-Bedroom Getaway by the Lake
Exterior
Bright & Cozy Two-Bedroom Getaway by the Lake
10.0 out of 10, Exceptional, (4)
"We thoroughly enjoyed our stay. It was easy to get hold of the owner for any questions we had. The layout worked well for our party of 4 adults. The location was perfect for our needs and we would definitely think about booking it again."
Bright & Cozy Two-Bedroom Getaway by the Lake
Dock Life Cottage 10 - Riverside, 2 Bedroom, Wasaga
Property grounds
Dock Life Cottage 10 - Riverside, 2 Bedroom, Wasaga
9.8 out of 10, Exceptional, (7)
"Very clean and kept up well. Just need a new shower head in the shower. It needs to tilt down more. We had a great time and ment great people. Made new friends and will be back next year."
Dock Life Cottage 10 - Riverside, 2 Bedroom, Wasaga
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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.

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 $109 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. 

Recent reviews in Simcoe County
Expedia verified reviews

Midland Inn & Suites

Midland Inn & Suites

5/5 Excellent
"Very nice ! Very clean ,comfortable beds ,basic but just what is required for amenities . And decent price for the area. The big chains could take note ! Definitely stay here again when in the area. "
A verified traveller stayed at Midland Inn & Suites
Posted 5 hours ago
Midland Inn & Suites