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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Featured Cottages in Cookstown and around

6 Bedroom Executive Cottage near Innisfil Beach - Special Winter Discount 20-35%
Smart TV, fireplace

6 Bedroom Executive Cottage near Innisfil Beach - Special Winter Discount 20-35%

9.8 out of 10, Exceptional, (75)
"We found the home perfect for our family, the six bedrooms and large couches and dining table plus a fantastic kitchen really made it easy to relax cook and enjoy each others company. We were totally pleased with Kaleem’s home and his acssesability for questions"
6 Bedroom Executive Cottage near Innisfil Beach - Special Winter Discount 20-35%
Spacious 5-Bedroom Vacation Home Near Lake Simcoe – Perfect for Family Gathering
Interior

Spacious 5-Bedroom Vacation Home Near Lake Simcoe – Perfect for Family Gathering

10.0 out of 10, Exceptional, (16)
"Goal was to spend Christmas day with family plus one extended family member from overseas out of the cramped condo and this cottage fit the bill perfectly. To better the chances of a white Christmas we chose a location close to Barrie but not too far north where we might get snowed in. The cottage is not lake-side or in a touristy area but we enjoyed using the BBQ grill and playing in the snow in the backyard. Inside was very clean and tidy with all the daily living essentials - note: there is...
Spacious 5-Bedroom Vacation Home Near Lake Simcoe – Perfect for Family Gathering
La Datcha Cottage Hot Tub, Sauna & Pool 20 Wooded Acres of Grassland
Outdoor spa tub

La Datcha Cottage Hot Tub, Sauna & Pool 20 Wooded Acres of Grassland

9.6 out of 10, Exceptional, (9)
"The house was over all great, it was a nice space for us 4 and 2 other families ( 8 people total) to stay while we were in town for our kids hockey tournament in Barrie. Living area was nice and open. Easy to move around the kitchen and living room. The kids really enjoyed the games table in the lower room. The hot tub was great, and once we figured out that the sauna was wood burning, we got that warned up and enjoyed that aswell. Kids explored the property and found a small frozen pond (...
La Datcha Cottage Hot Tub, Sauna & Pool 20 Wooded Acres of Grassland
Paradise Suites - Peaceful Getaway
Exterior

Paradise Suites - Peaceful Getaway

10.0 out of 10, Exceptional, (5)
"Worth it for a group to gather!"
The price is €681
includes taxes & fees
13 Feb - 14 Feb
Paradise Suites - Peaceful Getaway
ARCA Cozy Cabin-Innisfil Beach
Beach

ARCA Cozy Cabin-Innisfil Beach

8.0 out of 10, Very good, (1)
"Great spot for families"
ARCA Cozy Cabin-Innisfil Beach
Cheerful 4 Bedroom Cottage w/free Parking & WiFi, on Lake Simcoe
Interior

Cheerful 4 Bedroom Cottage w/free Parking & WiFi, on Lake Simcoe

10.0 out of 10, Exceptional, (1)
"The location was perfect for our Ice Fishing outing. The house has great sleeping accommodations. We found it to be nicely laid out. It was more expensive than we are used to paying over there. "
Cheerful 4 Bedroom Cottage w/free Parking & WiFi, on Lake Simcoe
Lake House-S/W Exposure! Hot Tub, Sandy Water, Game Rm!
Property grounds

Lake House-S/W Exposure! Hot Tub, Sandy Water, Game Rm!

9.8 out of 10, Exceptional, (34)
"We go away yearly a large group of ladies (11 this time) our NEED and must have is a big enough table for us all to sit at to play our cards, dice and any other game we choose, this had that. Property management was there for any beck and call which is always great, very prompt with a response which was greatly appreciated. Clean property, didn't really get to enjoy the outdoors as it was raining whole time there, close to town if you need anything which is nice. Lots of room for everyone,...
Lake House-S/W Exposure! Hot Tub, Sandy Water, Game Rm!
Cute family cottage getaway near Lake Simcoe!
Property grounds

Cute family cottage getaway near Lake Simcoe!

10.0 out of 10, Exceptional, (11)
"Excellent property and hosts have very quick communication. 10/10!"
Cute family cottage getaway near Lake Simcoe!
Exclusive Lakefront House on Private Lake
Terrace/patio

Exclusive Lakefront House on Private Lake

9.8 out of 10, Exceptional, (14)
"Loved the cottage, warm, comfortable, relaxing. Enjoyed staying two days over the holidays for a skiing getaway. Cathy was an amazing host and helped us with everything leaving up to the stay! Would love to visit again."
Exclusive Lakefront House on Private Lake
Cozy Cottage Across Lake Simcoe
Beach

Cozy Cottage Across Lake Simcoe

9.2 out of 10, Wonderful, (5)
"the premises were well received by our adult children and 1 dog. The beds were very comfortable with ample hot water.The only disappointment was the failure to plow the snow but our vehicles were able to get thru'"
Cozy Cottage Across Lake Simcoe
Luxury Lake Simcoe Waterfront Cottage
Aerial view

Luxury Lake Simcoe Waterfront Cottage

10.0 out of 10, Exceptional, (5)
"This home exceeded our expectations. Large, well built, almost new home with plenty of amenities. Our kids loved it!"
Luxury Lake Simcoe Waterfront Cottage
Utopia villa and spa
Outdoor dining

Utopia villa and spa

10.0 out of 10, Exceptional, (6)
"I booked this property for the week leading upto my wedding for myself and my groomsmen to hang out and unwind before the big day. This property was absolutely perfect, hard to say anything bad at all. A deceptively huge property has so much to offer, there is something for everyone, regardless of age. There are lawn games for kids, a pool table, darts and foosball for those a little older, plus a pool, hottub and sauna. There is even a ps5 for those who prefer to stay inside. There really is...
The price is €435
includes taxes & fees
2 Feb - 3 Feb
Utopia villa and spa
COZY COTTAGE WALKING DISTANCE TO LAKE SIMCOE & FRIDAY HARBOUR
Fridge, oven, stovetop, coffee/tea maker

COZY COTTAGE WALKING DISTANCE TO LAKE SIMCOE & FRIDAY HARBOUR

9.4 out of 10, Exceptional, (44)
"Great time as always!"
COZY COTTAGE WALKING DISTANCE TO LAKE SIMCOE & FRIDAY HARBOUR
LakeHouse S/W Exposure! Hot Tub, Sandy Water Game Room Lake Simcoe!
Terrace/patio

LakeHouse S/W Exposure! Hot Tub, Sandy Water Game Room Lake Simcoe!

9.6 out of 10, Exceptional, (5)
"Our group had a wonderful, relaxing and comfortable time at Ethan's cottage. The place is exactly as described and as pictured in the post. It is very clean and well-furnished to host large groups. There was more than enough dishes, utensils, glassware and linens to comfortably house our large group. We frequently rent cottages and Ethan's cottage is the cleanest and best one we've rented. We were very comfortable and would visit again. Ethan is a great host who is helpful, friendly,...
LakeHouse S/W Exposure! Hot Tub, Sandy Water Game Room Lake Simcoe!
3 Bedrooms Cottage W LAKE VIEWS, beside waterfront trail and steps from beach
Terrace/patio

3 Bedrooms Cottage W LAKE VIEWS, beside waterfront trail and steps from beach

9.0 out of 10, Wonderful, (4)
"I booked this property for my husband, brother and his family and myself to stay on the weekend of my daughter's wedding. The decor and atmosphere of the cottage was rustic romantic and perfect for hosting the rehearsal after party with the wedding party, getting the bridal party ready on the day of the wedding, and of course to enjoy being with our family. There was so much room for a family of 5 on one side of the house and my husband and I stayed in what can be described as a honeymoon suite....
3 Bedrooms Cottage W LAKE VIEWS, beside waterfront trail and steps from beach
Rustic Retreat: Spacious Cottage with Private Saltwater Pool and Sauna
Outdoor pool, a heated pool

Rustic Retreat: Spacious Cottage with Private Saltwater Pool and Sauna

Rustic Retreat: Spacious Cottage with Private Saltwater Pool and Sauna
Cottage W LAKE VIEWS, beside waterfront trail and steps from beach
Terrace/patio

Cottage W LAKE VIEWS, beside waterfront trail and steps from beach

8.8 out of 10, Excellent, (5)
"We had a great stay, the place was clean, organized and well kept "
Cottage W LAKE VIEWS, beside waterfront trail and steps from beach
Simcoe Georgina Family Cottage Winter-Summer Rent 1hr from Toronto
Snow and ski sports

Simcoe Georgina Family Cottage Winter-Summer Rent 1hr from Toronto

10.0 out of 10, Exceptional, (12)
"We really enjoyed our time! Thank you!"
Simcoe Georgina Family Cottage Winter-Summer Rent 1hr from Toronto
Beautiful Cottage Home By Innisfil Lake
Private kitchen

Beautiful Cottage Home By Innisfil Lake

9.0 out of 10, Wonderful, (2)
"The place has potential. Things that were not great were only 1 towel per bathroom but 4 bedrooms,locked thermostat, "
Beautiful Cottage Home By Innisfil Lake
Lake View Haven Cottage w/ Hot Tub and just Steps to Innisfil Beach!
Terrace/patio

Lake View Haven Cottage w/ Hot Tub and just Steps to Innisfil Beach!

10.0 out of 10, Exceptional, (1)
"Perfect weekend away with friends. Location was ideal and within walking distance to beach and trails. All communication with Michelle was prompt and helpful. House had many amenities including cute outdoor space with firepit, fire tables and a very clean hot tub. Beds and linens were comfortable. "
Lake View Haven Cottage w/ Hot Tub and just Steps to Innisfil Beach!
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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Other property types in Cookstown

Parkside House
Premium Apartment, 1 Queen Bed, Non Smoking, City View | Private kitchen

Parkside House

3.5 star property
9.4 out of 10, Exceptional, (282)
"great night stay, cozy & comfortable for a quick nights stay for my job. I wish the door had a dead bolt to feel more at ease but everything was great otherwise! "
The price is €94
includes taxes & fees
2 Feb - 3 Feb
Parkside House
Romantic Log Cabin in the Woods - Hot Tub under the Stars -80 km's from CN Tower
Exterior

Romantic Log Cabin in the Woods - Hot Tub under the Stars -80 km's from CN Tower

9.8 out of 10, Exceptional, (97)
"The pictures do not do this location justice. It's very cozy but not small by any means. Lots of places to relax, play games and enjoy the atmosphere. Property is well maintained both inside and out and the check-in process was very easy. We went to Keswick a few times and lots of nice places to shop and eat there. We will definately come back."
Romantic Log Cabin in the Woods - Hot Tub under the Stars -80 km's from CN Tower
6 Bedroom Executive Cottage near Innisfil Beach - Special Winter Discount 20-35%
Smart TV, fireplace

6 Bedroom Executive Cottage near Innisfil Beach - Special Winter Discount 20-35%

9.8 out of 10, Exceptional, (75)
"We found the home perfect for our family, the six bedrooms and large couches and dining table plus a fantastic kitchen really made it easy to relax cook and enjoy each others company. We were totally pleased with Kaleem’s home and his acssesability for questions"
6 Bedroom Executive Cottage near Innisfil Beach - Special Winter Discount 20-35%
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.

Frequently asked questions

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