Cookstown Vacation Rentals

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Vacation Rentals in Cookstown

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

9.6 out of 10, Exceptional, (14)
"We had a fantastic stay at the cottage with friends and kids! The place is surrounded by beautiful nature, perfect for a peaceful getaway. We really enjoyed the hot tub and sauna — a great way to relax after a day outdoors. The cottage was clean, cozy, and had everything we needed.Special thanks to our host Kirill — he was incredibly attentive, helpful, and made us feel very welcome. You can tell he truly cares about his guests' experience.Would definitely love to come back again!"
La Datcha Cottage Hot Tub, Sauna & Pool 20 Wooded Acres of Grassland

Parkside House

3.5 star property
9.4 out of 10, Exceptional, (294)
"Great experience"
The price is CA $113
CA $136 total
includes taxes & fees
Apr 22 - Apr 23
Parkside House

Residence & Conference Centre - King City

2.0 star property
8.0 out of 10, Very good, (378)
"Very quiet place to stay that offered 2 seperate rooms with small kitchen and fairly sized bathroom. The mattresses were pretty soft which didnt offer the ideal support."
The price is CA $102
CA $115 total
includes taxes & fees
May 12 - May 13
Residence & Conference Centre - King City

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

9.6 out of 10, Exceptional, (104)
"Watching rainfall on the skylight is amazing and very romantic. The board game nook has a low ceiling but once you’re sitting it isn’t an issue. Also playing games downstairs in front of the fireplace is fantastic. The bed is super comfortable. Much better than most places I’ve stayed. Marie is super easy to contact if you need her. A tree came down across the driveway while we were there and within a couple hours she came through with a truck and a chainsaw so we could make our checkout time....
Romantic Log Cabin in the Woods - Hot Tub under the Stars -80 km's from CN Tower

Residence & Conference Centre - Barrie

2.0 star property
7.0 out of 10, Good, (589)
"Good location. "
The price is CA $77
CA $86 total
includes taxes & fees
Apr 27 - Apr 28
Residence & Conference Centre - Barrie

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

9.2 out of 10, Wonderful, (27)
"Great stay everything was as described and good neighborhood "
Vacation Escape ~Sauna~Fireplace ~BBQ~ Outdoor Fire-pit ~Ping pong

The Mansion, Wasaga beach, Blue mountain

10.0 out of 10, Exceptional, (3)
"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!"
The price is CA $1,450
CA $2,498 total
includes taxes & fees
Apr 21 - Apr 22
The Mansion, Wasaga beach, Blue mountain

6 Bedroom Executive Cottage near Lake Simcoe & Innisfil Beach Park

9.8 out of 10, Exceptional, (77)
"Amazing owner, quick to reply to any questions. Fabulous house and large enough we didn’t feel under each others feet. Lovely little beach area at the bottom of the road and lots of places to visit from using the house as a central location. The intersection is quite busy but we rarely heard the traffic inside and sat on the veranda in the warm sunshine. Lovely little cafe next door too. "
6 Bedroom Executive Cottage near Lake Simcoe & Innisfil Beach Park

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

10.0 out of 10, Exceptional, (1)
"Giant house with lots of space and amenities for everyone!!! "
10-Bedroom, 9-Bathroom Luxury Retreat by Lake Simcoe | Ideal for Large Groups

Paradise Suites - Peaceful Getaway

9.4 out of 10, Exceptional, (6)
"Worth it for a group to gather!"
The price is CA $475
CA $947 total
includes taxes & fees
Apr 21 - Apr 22
Paradise Suites - Peaceful Getaway

Luxurious Spacious Dream Home with Parking!

8.0 out of 10, Very good, (4)
"Property was close enough to Venue .. A few updates in house would be nice Microwave was chipped and also a leak in bottom of main floor bthrm …, also bottom cupboard was off the hinge .. and pots and pans need to be replaced .., Overall house was very spacious and comfortable ! Would recommend it to friends "
The price is CA $180
CA $362 total
includes taxes & fees
Apr 21 - Apr 22
Luxurious Spacious Dream Home with Parking!

Black Water Golf Villa, Jackson's Point Harbour is 10 min drive

10.0 out of 10, Exceptional, (1)
"Great place not far from the city, big place and picture don’t do it justice. Pool was great, lots of area to play outdoors games check in was a breeze."
Black Water Golf Villa, Jackson's Point Harbour is 10 min drive

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

8.0 out of 10, Very good, (5)
"The house was just right for our group of 3 couples, 1 toddler and 2 dogs. The kitchen which is not depicted clearly in the listing, is large and easy to gather and eat in. The property is deep and is close to nature reserves, parks and the Bruce Trail. Frank is very frirndly andade certain that our stay was enjoyable."
House with 4.5 bedrooms,10 Acres of forest creek and trails, lots of parking

Large Estate with Luxury Collection of Amenities

9.8 out of 10, Exceptional, (47)
"The Good: The property was as advertised with all house amenities present and available. Exterior amenities would be amazing in the summer when all available.- Pool table, foosball and ping pong were great fun- BBQ, dining table, cutlery and dishware made a group meal easy- The provided toiletries were a plus- Bath / shower consumables were quality- Provided slippers, robes and towels were awesome.- The sauna worked well and was a huge hitThe bad: Due to snow the owner tried to cancel the agreed...
The price is CA $1,900
CA $2,956 total
includes taxes & fees
Apr 21 - Apr 22
Large Estate with Luxury Collection of Amenities

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

9.8 out of 10, Exceptional, (35)
"There 8 adult men in my group. We stayed 4 nights. We had a lot of gear since we were ice fishing. I asked each of them if they were happy with the accommodations. Each replied "yes." It suited this big group very nicely. All said they'd stay here again if we come back to fish. Very nice, big place!"
Lake House-S/W Exposure! Hot Tub, Sandy Water, Game Rm!

Bright, spacious 1200 sq foot apartment with Vaulted ceilings.

10.0 out of 10, Exceptional, (24)
"Host was very responsive and checked in to ensure everything was ok with my stay and despite the hosts home being attached, my privacy was respected. I would definitely recommend the property to others. "
The price is CA $160
CA $270 total
includes taxes & fees
Apr 21 - Apr 22
Bright, spacious 1200 sq foot apartment with Vaulted ceilings.

ARCA Cozy Cabin-Innisfil Beach

9.4 out of 10, Exceptional, (3)
"Lovely place , great host. Went for an ice fishing weekend with family and friends and had a blast . Was nice having access to the back shed / wood stove to dry out our equipment ! Thanks again for the stay ! "
The price is CA $150
CA $388 total
includes taxes & fees
Apr 27 - Apr 28
ARCA Cozy Cabin-Innisfil Beach

Cute family cottage getaway near Lake Simcoe!

10.0 out of 10, Exceptional, (12)
"Really enjoyed this cozy property as a weekend getaway! Everything was clean and it the hosts were kind and excellent to communicate with. "
Cute family cottage getaway near Lake Simcoe!

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

Welcome to our luxurious villa in the heart of downtown Newmarket!

9.6 out of 10, Exceptional, (4)
"Loved it here!! Go a head and book the host is amazing and his property is beautiful, I felt at home! "
The price is CA $450
CA $795 total
includes taxes & fees
Apr 21 - Apr 22
Welcome to our luxurious villa in the heart of downtown Newmarket!
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 types of properties in Cookstown you may be interested in

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

9.6 out of 10, Exceptional, (14)
"We had a fantastic stay at the cottage with friends and kids! The place is surrounded by beautiful nature, perfect for a peaceful getaway. We really enjoyed the hot tub and sauna — a great way to relax after a day outdoors. The cottage was clean, cozy, and had everything we needed.Special thanks to our host Kirill — he was incredibly attentive, helpful, and made us feel very welcome. You can tell he truly cares about his guests' experience.Would definitely love to come back again!"
La Datcha Cottage Hot Tub, Sauna & Pool 20 Wooded Acres of Grassland

Monte Carlo Inn Barrie Suites

3.0 star property
8.0 out of 10, Very good, (1929)
"Good value"
The price is CA $100
CA $120 total
includes taxes & fees
Apr 21 - Apr 22
Monte Carlo Inn Barrie Suites

Super 8 by Wyndham Barrie South

2.0 star property
7.6 out of 10, Good, (1362)
"Was down for medical appointments super8on whyndam staff were amazing very helpful very accommodating check in and out offogg"
The price is CA $88
CA $106 total
includes taxes & fees
Apr 27 - Apr 28
Super 8 by Wyndham Barrie South
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

Are there vacation rentals in Cookstown?

Yes, you can find vacation rentals near the most popular attractions in Cookstown, or you can select a more remote option if you're looking for a relaxing stay. Cookstown is known for its golf courses and shopping.

What's the top vacation rental that Cookstown has to offer?

Vacation Escape ~Sauna~Fireplace ~BBQ~ Outdoor Fire-pit ~Ping pong : This vacation home rental near Cookstown is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a private yard and a selection of games.

What’s there to see and do in Cookstown?

Explore the area and family-friendly sights such as Splashon Water Park Barrie, or get out into nature at a spot like Holland Marsh. Tanger Outlets and Innisfil Creek Golf Course are other places to visit while you're in town.

What’s a vacation rental in Cookstown like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Cookstown. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.