Cookstown Holiday Rentals

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Check prices for these dates

Tonight
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Cookstown holiday rentals

Fridge, microwave, oven, stovetop
Lakehouse Peaceful Cottage Modern Retreat - Pet Friendly!

Lakehouse Peaceful Cottage Modern Retreat - Pet Friendly!

Lakehouse Peaceful Cottage Modern Retreat - Pet Friendly!
Innisfil
10.0 out of 10, Exceptional, (1)
"The host is so awesome! They sent me a professional booklet before my stay. All questions answered promptly. I would recommend them again and again!!!"
Canada
Ashna
The price is HK$1,663
HK$2,149 total
includes taxes & fees
1 Jan - 2 Jan 2026
Lakehouse Peaceful Cottage Modern Retreat - Pet Friendly!
Exterior
Newly built and perfect for vacations. In the middle of both hwy 400&40

Newly built and perfect for vacations. In the middle of both hwy 400&40

Newly built and perfect for vacations. In the middle of both hwy 400&40
2.0 star property
Bradford West Gwillimbury
10.0 out of 10, Exceptional, (1)
"amazing all around "
Canada
Leshaun W.
The price is HK$1,364
HK$3,128 total
includes taxes & fees
30 Dec - 31 Dec
Newly built and perfect for vacations. In the middle of both hwy 400&40
Marina
Oasis Spa w/ Private Sauna!

Oasis Spa w/ Private Sauna!

Oasis Spa w/ Private Sauna!
2.0 star property
Innisfil
10.0 out of 10, Exceptional, (1)
"The Oasis Spa Getaway was a fantastic two night stay for my partner and I. The property was clean, modern and cozy! The unit had everything a couple needs for their stay including a sauna within the unit and a beautiful balcony. The host Michelle provided exceptional hospitality and was easy to connect with when needed. The location is great and only a short walk to the boardwalk and a quick two minute drive to the Nest golf course. The building’s pool was easy to access, quiet, and relaxing....
Canada
Matthew K.
The price is HK$1,156
HK$2,388 total
includes taxes & fees
2 Jan - 3 Jan 2026
Oasis Spa w/ Private Sauna!
Interior
Utopia villa and spa

Utopia villa and spa

Utopia villa and spa
Innisfil
10.0 out of 10, Exceptional, (9)
"Lots to do a great property."
Canada
Holly S.
The price is HK$1,478
HK$3,726 total
includes taxes & fees
6 Jan - 7 Jan 2026
Utopia villa and spa
Interior
Lake Simcoe 4-Bedroom Home 5 Minutes to Beach Park

Lake Simcoe 4-Bedroom Home 5 Minutes to Beach Park

Lake Simcoe 4-Bedroom Home 5 Minutes to Beach Park
Innisfil
10.0 out of 10, Exceptional, (22)
"Homey with ample space. "
United States
Daphne
The price is HK$795
HK$2,864 total
includes taxes & fees
5 Jan - 6 Jan 2026
Lake Simcoe 4-Bedroom Home 5 Minutes to Beach Park
Fridge, microwave, oven, stovetop
Studio apartment 3mins from Carrying Place Golf Club & The Manor. Off HW 400

Studio apartment 3mins from Carrying Place Golf Club & The Manor. Off HW 400

Studio apartment 3mins from Carrying Place Golf Club & The Manor. Off HW 400
Kettleby, King City
10.0 out of 10, Exceptional, (1)
"Nice place"
Canada
mike
The price is HK$540
HK$1,105 total
includes taxes & fees
30 Dec - 31 Dec
Studio apartment 3mins from Carrying Place Golf Club & The Manor. Off HW 400
Private kitchen
The Allandale Residence

The Allandale Residence

The Allandale Residence
Barrie
10.0 out of 10, Exceptional, (3)
"Clean pet friendly would be pleased to stay again "
Canada
Michael P.
The price is HK$853
HK$2,190 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Allandale Residence
Fridge, microwave, oven, stovetop
Modern 4 Bedroom Townhouse in Barrie South

Modern 4 Bedroom Townhouse in Barrie South

Modern 4 Bedroom Townhouse in Barrie South
Barrie
9.2 out of 10, Wonderful, (17)
"It was a decent place to sleep with comfortable beds. Parking very good. We were 6 guests. "
Canada
Elna S.
The price is HK$859
HK$1,972 total
includes taxes & fees
2 Jan - 3 Jan 2026
Modern 4 Bedroom Townhouse in Barrie South
Interior
5 minutes from the lake! Brand new condo at Jackson's Point, Georgina

5 minutes from the lake! Brand new condo at Jackson's Point, Georgina

5 minutes from the lake! Brand new condo at Jackson's Point, Georgina
Georgina
9.8 out of 10, Exceptional, (7)
"Great location! Rental was clean and exactly as listed. "
Canada
Laura W.
The price is HK$1,137
HK$2,055 total
includes taxes & fees
30 Dec - 31 Dec
5 minutes from the lake! Brand new condo at Jackson's Point, Georgina
Terrace/patio
Luxurious Spacious Dream Home with Parking!

Luxurious Spacious Dream Home with Parking!

Luxurious Spacious Dream Home with Parking!
Richmond Hill
9.0 out of 10, Wonderful, (13)
"Had a great time - thank you!"
Canada
Curtis B.
The price is HK$921
HK$1,927 total
includes taxes & fees
2 Jan - 3 Jan 2026
Luxurious Spacious Dream Home with Parking!
Fridge, microwave, oven, stovetop
Cozy house at south end Barrie

Cozy house at south end Barrie

Cozy house at south end Barrie
Barrie
9.8 out of 10, Exceptional, (10)
"Excellent, clean property with all the necessary amenities. "
Canada
John
The price is HK$813
HK$2,152 total
includes taxes & fees
15 Jan - 16 Jan 2026
Cozy house at south end Barrie
Property grounds
New, Clean and Comfortable Apartment with Private Entrance.

New, Clean and Comfortable Apartment with Private Entrance.

New, Clean and Comfortable Apartment with Private Entrance.
East Gwillimbury
10.0 out of 10, Exceptional, (6)
"Clean apartment, spacious, nice neighbourhood"
Canada
Peter v.
The price is HK$819
HK$1,291 total
includes taxes & fees
4 Jan - 5 Jan 2026
New, Clean and Comfortable Apartment with Private Entrance.
Marina
Friday Harbour, 2BR pet friendly

Friday Harbour, 2BR pet friendly

Friday Harbour, 2BR pet friendly
Innisfil
9.0 out of 10, Wonderful, (4)
"Visiting family "
Canada
Elizabeth T.
The price is HK$663
HK$1,938 total
includes taxes & fees
3 Jan - 4 Jan 2026
Friday Harbour, 2BR pet friendly
Fridge, microwave, oven, stovetop
Barrie house close to all amenities

Barrie house close to all amenities

Barrie house close to all amenities
Barrie
9.0 out of 10, Wonderful, (29)
"The accommodations were very comfortable and met our needs. Very close to shops and highways to access any part of the city. Quick response by host. "
Canada
Heather B.
The price is HK$895
HK$2,393 total
includes taxes & fees
4 Jan - 5 Jan 2026
Barrie house close to all amenities
Exterior
Luxury 2BR/2BA Retreat + Netflix + Free Parking –Lake Wilcox-Richmond Hill-VRBO

Luxury 2BR/2BA Retreat + Netflix + Free Parking –Lake Wilcox-Richmond Hill-VRBO

Luxury 2BR/2BA Retreat + Netflix + Free Parking –Lake Wilcox-Richmond Hill-VRBO
Richmond Hill
10.0 out of 10, Exceptional, (2)
"This was our first time in a VRBO and what a fabulous experience! From booking to check out the communication with the owner was fantastic. They were pleasant, friendly and very accommodating! We highly recommend this property to stay at for yourself or a family! "
Canada
Lisa T.
The price is HK$967
HK$1,972 total
includes taxes & fees
11 Jan - 12 Jan 2026
Luxury 2BR/2BA Retreat + Netflix + Free Parking –Lake Wilcox-Richmond Hill-VRBO
Interior
Spacious 2BR Basement Apt – 5 Mins to Beach

Spacious 2BR Basement Apt – 5 Mins to Beach

Spacious 2BR Basement Apt – 5 Mins to Beach
2.0 star property
Innisfil
The price is HK$669
HK$1,444 total
includes taxes & fees
4 Jan - 5 Jan 2026
Spacious 2BR Basement Apt – 5 Mins to Beach
Property grounds
Lakeside Private suite (Queen bed room)

Lakeside Private suite (Queen bed room)

Lakeside Private suite (Queen bed room)
Loretto
The price is HK$546
HK$918 total
includes taxes & fees
30 Dec - 31 Dec
Lakeside Private suite (Queen bed room)
4 bedrooms, desk, iron/ironing board, WiFi
Spacious 4 Bedroom House in Angus

Spacious 4 Bedroom House in Angus

Spacious 4 Bedroom House in Angus
Angus
9.4 out of 10, Exceptional, (3)
"Like i mentioned to our host it was on our top 3 list of places we stayed . The beds, livingroom and location was great. I commented to our host a few suggestion that could help in future guests. Iwould definitely recommend this location to friends and family."
Canada
Mary W.
The price is HK$913
HK$2,130 total
includes taxes & fees
1 Jan - 2 Jan 2026
Spacious 4 Bedroom House in Angus
Fridge, microwave, oven, stovetop
Central & Cozy 2BR Townhome—Steps to Plaza, 5 Min Drive to Innisfil Beach Park!

Central & Cozy 2BR Townhome—Steps to Plaza, 5 Min Drive to Innisfil Beach Park!

Central & Cozy 2BR Townhome—Steps to Plaza, 5 Min Drive to Innisfil Beach Park!
Innisfil
8.8 out of 10, Excellent, (3)
"We had a great trip! The place was very clean and the host was easy to contact. It was also right next to a plaza with a No Frills and many other places to eat."
Canada
Isabella S.
The price is HK$752
HK$2,038 total
includes taxes & fees
12 Jan - 13 Jan 2026
Central & Cozy 2BR Townhome—Steps to Plaza, 5 Min Drive to Innisfil Beach Park!
Terrace/patio
Fire & Ice Spa w/ Private Sauna!

Fire & Ice Spa w/ Private Sauna!

Fire & Ice Spa w/ Private Sauna!
Innisfil
9.8 out of 10, Exceptional, (9)
"Had an amazing stay. Property feels just like home. Good idea to look ahead make sure your favourite restaurant is open. "
Canada
Alex W.
The price is HK$1,222
HK$2,568 total
includes taxes & fees
30 Dec - 31 Dec
Fire & Ice Spa w/ Private Sauna!
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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Top Cookstown Hotel Reviews

Microtel Inn & Suites by Wyndham Aurora

Microtel Inn & Suites by Wyndham Aurora

10/10 Excellent
"This is the second multi night stay for our family at this hotel and it will certainly not be the last. Staff is wonderfully helpful, the rooms are clean, the breakfast is consistent. The hotel is vibrant and bustling; the kids cannot wait to come back"
Karen 3-night trip
Posted 1 day ago
Microtel Inn & Suites by Wyndham Aurora

Find out more about Cookstown

Search for holiday rentals in Cookstown on Expedia! You can easily find your home rentals, villas, holiday apartments in Cookstown using one of the methods below:

  • View our selection of featured holiday rentals in Cookstown
  • Use the map to find apartments and other holiday homes in the Cookstown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cookstown while they last

Look no further and take a look at our great range of rental properties in Cookstown!

Frequently asked questions

Are there holiday rentals in Cookstown?

Yes, there are holiday rentals close to the most popular sights in Cookstown, or you can select a more secluded option if you're looking for a relaxing stay. Cookstown is known for its golf courses and shopping.

What are some of the best holiday rentals that Cookstown has to offer?

6 Bedroom Executive Cottage near Lake Simcoe & Innisfil Beach Park: This holiday home rental outside of Cookstown is located on a lake, and has a fireplace, a furnished patio and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

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 Landing Prairie Provincial Park. Tanger Outlets and Innisfil Creek Golf Course are other places to visit while you're in town.

What’s a holiday rental in Cookstown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cookstown. Holiday rentals offer amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family gatherings.