Simcoe County Holiday Rentals

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Top Cities in Simcoe County

Collingwood featuring heritage architecture

Top Holiday Rentals Destinations in Simcoe County

"Great property and value. May I suggest having a hair dryer and iron/ironing board in the room. I highly recommend this property. "

includes taxes & fees

28 Nov - 29 Nov

"TITLE: "Betrayal of Trust: A Family's Heartbreaking Encounter at Cottage of Tiny Beaches" ● WHY THE TITLE: This title emphasizes the sense of betrayal and disappointment my family experienced during our stay, highlighting the trust that was broken due to the subpar treatment and unmet expectations. ⚓️ With profound sadness and disillusionment, I share our family's distressing experience at the Cottage of Tiny Beaches in Georges Bay, Ontario. As a proud member of the esteemed Neri family, with...

Desk, iron/ironing board, free WiFi, bed sheets

"A+"

includes taxes & fees

24 Nov - 25 Nov

"Great stay, host was responsive and place had lots to do! Comfy place, clean. Loved the firepit and back area."

"The property manager was exceptionally helpful. Thanks so much."

"This home was perfect for 5 seniors. Close to Scandanave Spa. Very quiet. Fully equipped and clean. Not recommended for those with mobility problems as bedrooms were upstairs"

includes taxes & fees

24 Nov - 25 Nov

"Great stay. Great host. Be sure to bring your own supplies though because the gas station and convenience stores have a huge markup. Would definitely go back again."

includes taxes & fees

24 Nov - 25 Nov

"12 longtime friends who want to catch up. We chat, eat, drink, dance, sing, shop, do crafts, take walks and laugh and laugh and laugh. We had an awesome time and loved our accommodations. Thank you."

"This cabin is cozy, well-appointed and absolutely perfect for two. And the property it is situated on is incredible! The ponds, the gardens, the stone paths, the dock, the firepit, the trail through the woods, the wraparound porch, multiple sitting areas, and the privacy!! Nothing but "10s" all around. We caught amazing sunsets, and have fabulous pics of the early morning sun setting the autumn colours ablaze all around us. It was very relaxing and very peaceful. Highly recommend. "

Indoor pool, outdoor pool, open noon to 8:00 PM, lifeguards on site

"The studio apartment is in a lovely complex - beautiful in the fall with the changing leaves and a nice residential type area to walk around in. It’s close to some nice family activities - tree top trekking, horseback riding and I understand there are skiing options nearby in winter. A highlight for me was that it was walking distance to the Vettä Nordic spa. Dining in the area was a bit limited, but I was able to order Uber Eats when I wanted it (from Barrie). The kitchen in the studio is a...

"We came with a group of 15 in mid November and had a great time, the place is very nice and clean, great TV and internet. Lots of space and couches, chairs. Thought everything went fine. Communication was great, would stay again. Right by st.louis, moonstone for skiers, we all went for a hike. Thanks!"

includes taxes & fees

24 Nov - 25 Nov

"Was the best equipped cottage out of the 3 I have booked and stayed at at wasaga. Perfect location, wonderful hosts,well equipped. I will definitely go back...."

"utilities was not as required and also the barbecue was not working over all the stay was nice and my friends and family really like"

includes taxes & fees

30 Nov - 1 Dec

"It was amazing. We've stayed at a different cottage number last year and this year was nothing short but amazing. We had a great time. Location is perfect. Communication is clear and never waiting for a response. This property makes our vacation."

"We wished we could have stayed longer!!Grandchildren, loved the pool. Lots of room for entertaining. Close to walking trails and the Bay."

"We had an absolutely delightful stay at this property! The house was clean, spacious, and beautifully maintained, providing us with all the comfort we could ask for. The exterior amenities, including the pool and the well-kept patio area, made for perfect mornings and evenings spent outdoors. The property owner was incredibly attentive and hospitable, ensuring our stay was smooth and enjoyable from start to finish. Highly recommend this gem for anyone seeking a relaxing and luxurious getaway!"

includes taxes & fees

23 Dec - 24 Dec

"Grandparents with adult children and their two children. It was a great place to relax and fishing off the dock was great. The beach is beautiful"

1 bedroom, desk, iron/ironing board, free WiFi

"We had a great stay here. The unit was very clean and was a beautiful space. Would recommend!"

includes taxes & fees

1 Dec - 2 Dec

"Awesome natural surroundings. Cottage vibes and a lot of space for activities. Not giving 5 stars only because of power outage in the town which not really was anyone’s fault but we ended up wasting 4 hours of our trip with no water or electricity. "

includes taxes & fees

25 Nov - 26 Nov

"The home showed beautifully like something you would see in a magazine. Everything was well thought out so had all the necessities you need and more. And a lovely private outside area. The location was perfect a block away from downtown and a few blocks from the bay. Park right in front and forget driving until you leave."

includes taxes & fees

27 Nov - 28 Nov

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Find out more about Simcoe County

Everything you need to know about Simcoe County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Simcoe County holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Simcoe County holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Simcoe County holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Simcoe County holiday rentals we have chosen for you start as low as AU$223 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 holiday 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 holiday.

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.

Simcoe County Holiday Home Travel Info

Holiday homes	51
Popular accommodation	Simcoe County private holiday homes
Known landmarks	Snow Valley Ski Resort, Elmvale Jungle Zoo and Creemore Springs Brewery
International airports	Toronto, ON (YYZ-Pearson Intl.), Toronto, ON (YTZ-Billy Bishop Toronto City) and Hamilton, ON (YHM-John C. Munro Hamilton Intl.)