Cookstown Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Browse Select Cookstown Vacation Homes

Luxurious Spacious Dream Home with Parking!

8.4 out of 10, Very good, (8)
"Clean, sleek, and large—fully detached house. Host was communicative, accommodating, and nice through the entire process."
The price is CA $180
CA $362 total
includes taxes & fees
Aug 26 - Aug 27
Luxurious Spacious Dream Home with Parking!

Beautiful, cozy and peaceful 2-bedroom and 1.5 bath home in Barrie

Beautiful, cozy and peaceful 2-bedroom and 1.5 bath home in Barrie

The Caledon Retreat

10.0 out of 10, Exceptional, (2)
"amazing stay , great communication, beautiful house , had many assets to make your stay comfortable will definitely be coming back !"
The price is CA $700
CA $904 total
includes taxes & fees
Aug 12 - Aug 13
The Caledon Retreat

Lake Simcoe Waterfront Villa | Walk to lake · Free canoes · BBQ & firepit

9.8 out of 10, Exceptional, (10)
"Beautiful, spacious house exactly as advertised with lovely grounds and view of the water. Great for a large group. "
The price is CA $919
CA $1,767 total
includes taxes & fees
Aug 12 - Aug 13
Lake Simcoe Waterfront Villa | Walk to lake · Free canoes · BBQ & firepit

Wonderful place of Lake Simkoe

9.0 out of 10, Wonderful, (7)
"We only stayed 1 night but it was perfect "
The price is CA $117
CA $345 total
includes taxes & fees
Aug 12 - Aug 13
Wonderful place of Lake Simkoe

Private Boyne River Cottage- steps to great fishing

Private Boyne River Cottage- steps to great fishing

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

9.4 out of 10, Exceptional, (78)
"Great stay. Excellent location and beautiful outdoor area."
Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!

5br 3.5bth home w Free Parkings+Ensuite laundry Barrie,ON

10.0 out of 10, Exceptional, (3)
"Wonderful stay — clean, comfortable, and exactly as described. Great host, smooth check-in, quiet and convenient location. Highly recommend and would gladly return!"
The price is CA $171
CA $467 total
includes taxes & fees
Aug 25 - Aug 26
5br 3.5bth home w Free Parkings+Ensuite laundry Barrie,ON

CHARMING CUSTOM HOME BESIDE PARK,WALK TO BEACH

9.8 out of 10, Exceptional, (23)
"Excelent Property. Peter was an excelent communicator I would stay there again"
CHARMING CUSTOM HOME BESIDE PARK,WALK TO BEACH

5-Bedroom Countryside Estate in Northern GTA – Ideal for Gatherings & Getaways

10.0 out of 10, Exceptional, (1)
"House was very nice, lots of space. Stay was very nice, Jagjit was a great host in being generous. I would book again and i suggest you book here. "
5-Bedroom Countryside Estate in Northern GTA – Ideal for Gatherings & Getaways

Cozy house for a young family. Live in the Heart of It All!

10.0 out of 10, Exceptional, (1)
"Very nice clean property, with available necessary amenities, in quiet neighborhood. Smooth communications with easy Check-In and Check-Outs. Not an issue for us, but listings needs to be corrected to state ONE QUEEN BED in each bedroom; not the listed 2 Queen Beds in each room. Overall we enjoyed our stay. Thank You."
Cozy house for a young family. Live in the Heart of It All!

Cozy 3 bedroom home perfect for small gatherings

8.0 out of 10, Very good, (1)
"The property was nice, neat and tidy. The inside was clean and very spacious. The beds were extremely comfortable as well. "
Cozy 3 bedroom home perfect for small gatherings

Entire Cheerful House

8.8 out of 10, Excellent, (9)
"We had a great stay in this house. There was so much room and it was very well equipped. Would definitely stay again!"
Entire Cheerful House

Vacation Home on Simcoe lake

Vacation Home on Simcoe lake

Neat Cozy Family Friendly Home

10.0 out of 10, Exceptional, (1)
"Super nice neighborhood lots of kids playing at a basketball court within the neighborhood property the house was a little bit older but it was nice and warm feeling 10/10 would stay again "
The price is CA $139
CA $486 total
includes taxes & fees
Aug 15 - Aug 16
Neat Cozy Family Friendly Home

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

9.2 out of 10, Wonderful, (33)
"Rooms with multiple bed made it really easy and nice for our group of friends to stay. The main sitting area was nice to hang out. The extra fee for extra people was tough cause not everyone was able to come. "
Vacation Escape ~Sauna~Fireplace ~BBQ~ Outdoor Fire-pit ~Ping pong

Barrie house close to all amenities

9.0 out of 10, Wonderful, (24)
"Everything about the property was great! The ease of communication with the owner to the amenities all around. The house was spacious and clean. Would highly recommend and definitely will be back! Thank you for a great weekend away!"
The price is CA $140
CA $399 total
includes taxes & fees
Aug 12 - Aug 13
Barrie house close to all amenities

Luxurious Lake front Island Twnhome Friday Harbour

8.8 out of 10, Excellent, (9)
"We enjoyed our stay here during a major storm. The home was very welcoming and suited our needs . "
Luxurious Lake front Island Twnhome Friday Harbour

4 Bedroom Spacious Enclave near Lake Wilcox

The price is CA $224
CA $672 total
includes taxes & fees
Sep 7 - Sep 8
4 Bedroom Spacious Enclave near Lake Wilcox

GLOBALSTAY 4-Bd House Near Lake Simcoe

5.0 star property
8.0 out of 10, Very good, (1)
"We loved this place but number one issue they were charging $16 for each trash bag and second so many rules about guest and spending time at property and they mentioned that after we booked the place.Other issue we couldn’t find towel there after 24 hours we found it in dryer and no second key in lock box for 2 familles. Overall place was so clean comfortable and nice."
GLOBALSTAY 4-Bd House Near Lake Simcoe
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cookstown Hotel Reviews