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Compare 223 Vacation Homes in Cookstown with updated reviews, rates, and availability.

10-Bedroom, 9-Bathroom Luxury Retreat by Lake Simcoe | Ideal for Large Groups

9.0 out of 10, Wonderful, (2)
"Giant house with lots of space and amenities for everyone!!! "
10-Bedroom, 9-Bathroom Luxury Retreat by Lake Simcoe | Ideal for Large Groups

Vacation Escape ~Sauna~Fireplace ~BBQ~ Outdoor Fire-pit ~Ping pong

9.2 out of 10, Wonderful, (27)
"We really enjoyed staying at Natalya place. House was very clean, cozy, and stocked with everything we needed. Natalya was very quick to answer all our questions. Unfortunately, weather didn't  cooparate so we didn't have chance to learn more about local amenities. We would love to stay here again."
Vacation Escape ~Sauna~Fireplace ~BBQ~ Outdoor Fire-pit ~Ping pong

House with 4.5 bedrooms,10 Acres of forest creek and trails, lots of parking

8.0 out of 10, Very Good, (6)
"The property was fantastic to stay at. We had a beautiful fire, lots of open space Frank was a pleasure to deal with the house was nice and big.Everything was provided for us that we needed"
House with 4.5 bedrooms,10 Acres of forest creek and trails, lots of parking

Luxurious Spacious Dream Home with Parking!

8.0 out of 10, Very Good, (4)
"House was perfect. Stayed for hockey tournament. Close to arenas and all other amenities. Small driveway but everything else was great. Would definitely stay again. "
The price is AED 477
AED 959 total
includes taxes & fees
11 May - 12 May
Luxurious Spacious Dream Home with Parking!

Charming 3-bedroom house with AC, WiFi in lovely Barrie

6.0 out of 10, (1)
"Good location. Host was very fast and responsive. We and a good stay! "
The price is AED 928
AED 1,199 total
includes taxes & fees
3 May - 4 May
Charming 3-bedroom house with AC, WiFi in lovely Barrie

"Luxury Event House with Pool, Hot Tub, and Outdoor Bar"

"Luxury Event House with Pool, Hot Tub, and Outdoor Bar"

Barrie house close to all amenities

9.4 out of 10, Exceptional, (20)
"It's our third time staying at this property and it is perfect for our needs. Host is very responsive and property is well kept, clean and well stocked. "
The price is AED 398
AED 1,079 total
includes taxes & fees
2 Jun - 3 Jun
Barrie house close to all amenities

Welcome to Lake House by Lis, where stunning lake views and serene sunsets await

9.4 out of 10, Exceptional, (9)
"Place is as advertised. No complaints. Lots of space for a chill weekend."
Welcome to Lake House by Lis, where stunning lake views and serene sunsets await

Entire Cheerful House

9.0 out of 10, Wonderful, (7)
"Ideally located only 10 minutes from my son’s wedding venue in a quiet neighborhood close to amenities (read, walking distance to Starbucks!). Clean and comfortable with a kind and responsive host."
Entire Cheerful House

Tranquil Haven

3.0 star property
Tranquil Haven

Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!

9.4 out of 10, Exceptional, (73)
"We had a great time amazing property great location, beautiful grounds! We can’t wait to return next year"
Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!

5 Bedroom Countryside-Cottage King ON - 35% Winter & Long Stay Discount.

9.6 out of 10, Exceptional, (20)
"We loved the home and felt comfortable in every way while we stayed. "
5 Bedroom Countryside-Cottage King ON - 35% Winter & Long Stay Discount.

Affordable 1BR Newmarket

7.2 out of 10, Good, (5)
"The property is clean and quiet."
The price is AED 133
AED 384 total
includes taxes & fees
5 May - 6 May
Affordable 1BR Newmarket

This house is a 4 bedroom(s), 2.5 bathrooms, located in Barrie, ON.

7.4 out of 10, Good, (6)
"Very clean, tidy and quiet."
The price is AED 446
AED 1,056 total
includes taxes & fees
4 May - 5 May
This house is a 4 bedroom(s), 2.5 bathrooms, located in Barrie, ON.

New 4 Bedroom Townhouse in Barrie South

9.6 out of 10, Exceptional, (13)
"Was great!"
The price is AED 395
AED 884 total
includes taxes & fees
26 May - 27 May
New 4 Bedroom Townhouse in Barrie South

A family-friendly getaway, with outdoor pool and beautiful view!

10.0 out of 10, Exceptional, (1)
"2nd time in this home-lovely place, delightful pool and beautiful views of a small marsh. Very comfortable and fully outfitted."
A family-friendly getaway, with outdoor pool and beautiful view!

A Comfort House in Barrie

7.4 out of 10, Good, (3)
"We had a lovely time staying in Barrie for our son’s wedding. The house is dated but equipped with everything you need for family to stay for a little getaway. Lenny was lovely and quickly responded to our questions. Thx for a lovely, reasonably priced mini vacation x"
A Comfort House in Barrie

Live large in a cozy space

Live large in a cozy space

New 4 Bedroom House in Angus

10.0 out of 10, Exceptional, (1)
"The house was located in a very nice neighborhood, just a five minute drive to many amenities. The house is spacious and comfortable with plenty of bedrooms. Beautiful walking trails right across the street!"
The price is AED 448
AED 986 total
includes taxes & fees
1 Jun - 2 Jun
New 4 Bedroom House in Angus

Private Boyne River Cottage- steps to great fishing

The price is AED 796
AED 1,369 total
includes taxes & fees
16 May - 17 May
Private Boyne River Cottage- steps to great fishing
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

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

9.6 out of 10, Exceptional, (14)
"Great property and house - very much enjoyed our time there"
La Datcha Cottage Hot Tub, Sauna & Pool 20 Wooded Acres of Grassland

Parkside House

3.5 star property
9.4 out of 10, Exceptional, (296)
"Owner met us and showed us around."
The price is AED 293
AED 351 total
includes taxes & fees
5 May - 6 May
Parkside House

Residence & Conference Centre - King City

2.0 star property
8.0 out of 10, Very Good, (378)
"Everything was amazing, I loved staying here!"
The price is AED 270
AED 306 total
includes taxes & fees
12 May - 13 May
Residence & Conference Centre - King City
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.