Top Chalets in Simcoe County in 2025

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Top Cities in Simcoe County

Collingwood which includes heritage architecture

Featured Chalets in Simcoe County

"This home was perfect for our large group of adults. The home was very clean and well-stocked for our needs. Each bedroom had a bathroom, which was a huge hit! The home is extra spacious and perfect for entertaining! The check-in/out process was easy! The outdoor space was perfect for summer enjoyment! My only complaint was the temperature of the home. It was very warm despite having AC, and we weren't able to adjust the temperature, nor did the host. It was very hot to sleep. There are no fans,...

Situated in a serene snowy landscape, this outdoor space features a picnic table and fire pit, perfect for relaxation and outdoor activities.

"Short stay to go skiing at Mount St. Louis Moonstone, and enjoy dining out in the area (Ktchn). House was as described, clean, organized and comfortable. Little inconvenient to have only a first floor bathroom but it was spacious. Enjoyed our stay."

Relax in style on this outdoor patio with sofas, tables, and lush greenery, surrounded by a glass wall and a chandelier.

"Stayed at this chalet for a summer golf weekend, and it was awesome! The beautiful building has been thoughtfully and tastefully renovated from an old church and shows tons of character, yet has all the modern conveniences needed.The location was private and quiet, but close enough to several golf courses and restaurants that we never had to drive all that far.Would gladly stay again or recommend to those looking for a great vacation rental in the area."

Surround yourself with serene mountain views and unwind by the central pool.

"We spent the past several days at Andrea's property with the family. It was a truly fantastic experience as the property was absolutely beautiful, and everything you could possibly require was provided. Andrea was a fantastic host and communication was fantastic. We look forward to returning!"

Relax in a serene garden setting with an outdoor seating area featuring a table and chairs.

Stroll through a serene garden surrounded by lush foliage and a tranquil stream.

Relax by the pool in the designated shallow area, surrounded by lounge chairs and umbrellas.

"Highly recommended"

Relax on the cabin's deck, surrounded by nature, with a seating area and wood-burning stove.

Classic brick building with a pitched roof and decorative trim, home to Bonnie Dorgelo Jewellery and Paintings.

Enjoy cooking in this well-equipped kitchen with a large window, stainless steel appliances, and ample cabinetry.

"The stay was wonderful! Very clean and easy to keep clean as well! Our host was lovely and was available when we had needed her. We booked our little getaway mid-week as I was able to get a day off work so we could travel there. I needed to work the remainder of the week still and was concerned that the internet service may not have been strong enough as I work in a queue and take my calls through the internet/wifi, so strength and stability is extremely important. Our wonderful host assured me...

Enjoy a warm and inviting atmosphere on the covered porch, surrounded by serene winter landscapes.

Surrounded by lush greenery, this cabin features a central entrance and two windows on each side.

Compact kitchen with refrigerator, microwave, coffee maker, and oven, featuring ample storage and a simple layout.

Surround yourself with serene natural beauty and unwind by the pool, surrounded by cozy cabins.

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Simcoe County Hotel Reviews

Candlewood Suites Collingwood by IHG

10/10 Excellent

"Comfortable bed. Great pillows. Quiet room. No street noise and Air Conditioner not too loud. Nice shower with good water pressure and no drainage issues. Our room had a big fridge and full size dishwasher. Tim Hortons across the street, but also a complementary coffee machine in the lobby and room "