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Cookstown Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Cookstown vacation rentals

Coffee/tea maker, fridge, microwave, oven

1. Full House, 4KM near waterfront

Full House, 4KM near waterfront
Letitia Heights
The price is ￥29,997
￥65,261 total
includes taxes & fees
Oct 1 - Oct 2
Full House, 4KM near waterfront
Coffee/tea maker, fridge, microwave, oven

2. Lake Simcoe Waterfront Retreat | Expansive Private Grounds · Ideal for Groups

Lake Simcoe Waterfront Retreat | Expansive Private Grounds · Ideal for Groups
Gilford
9.6 out of 10, Exceptional, (19 reviews)
"Nice and clean place . "
Canada
zeshan r.
The price is ￥132,238
￥256,273 total
includes taxes & fees
Sep 20 - Sep 21
Lake Simcoe Waterfront Retreat | Expansive Private Grounds · Ideal for Groups
Smart TV

3. Lakehouse Peaceful Cottage Modern Retreat - Pet Friendly!

Lakehouse Peaceful Cottage Modern Retreat - Pet Friendly!
Innisfil
8.0 out of 10, Very good, (2 reviews)
"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 ￥36,229
￥45,977 total
includes taxes & fees
Sep 27 - Sep 28
Lakehouse Peaceful Cottage Modern Retreat - Pet Friendly!
TV

4. Brand New Luxury Modern Above Ground Suite Bond Head Retreat/Peaceful

Brand New Luxury Modern Above Ground Suite Bond Head Retreat/Peaceful
Bond head
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home and the host was very accommodating. One of the best places to stay in the area."
United States
A A.
The price is ￥16,942
￥30,552 total
includes taxes & fees
Sep 28 - Sep 29
Brand New Luxury Modern Above Ground Suite Bond Head Retreat/Peaceful
Living area

5. Warm & Cozy 3BR Retreat!

Warm & Cozy 3BR Retreat!
Bradford West Gwillimbury
10.0 out of 10, Exceptional, (2 reviews)
"Would rent again!"
United States
Jessica F.
The price is ￥19,508
￥39,553 total
includes taxes & fees
Sep 22 - Sep 23
Warm & Cozy 3BR Retreat!
TV, fireplace

6. The Chieftain Suite

The Chieftain Suite
Barrie
9.6 out of 10, Exceptional, (17 reviews)
"Very clean and quiet place to stay! Communication was great and I was able to check in an hour early."
Canada
Kaitlyn
The price is ￥12,262
￥23,681 total
includes taxes & fees
Sep 29 - Sep 30
The Chieftain Suite
Interior

7. Clean & Cozy Home Near Downtown

Clean & Cozy Home Near Downtown
New Tecumseth
8.4 out of 10, Very good, (6 reviews)
"Very cozy stay for a weekend hockey tournament."
Canada
Suzanne
The price is ￥12,786
￥30,291 total
includes taxes & fees
Sep 21 - Sep 22
Clean & Cozy Home Near Downtown
Living area

8. Family/Group: Cozy 3BR Entire Home

Family/Group: Cozy 3BR Entire Home
Bradford West Gwillimbury
The price is ￥16,824
￥36,248 total
includes taxes & fees
Oct 5 - Oct 6
Family/Group: Cozy 3BR Entire Home
Private kitchen

9. Innisfil Getaway

Innisfil Getaway
Innisfil
The price is ￥27,757
￥50,260 total
includes taxes & fees
Sep 21 - Sep 22
Innisfil Getaway
Coffee/tea maker, fridge, microwave, oven

10. 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
7.4 out of 10, Good, (3 reviews)
"Nice place"
Canada
mike
The price is ￥11,216
￥22,560 total
includes taxes & fees
Oct 4 - Oct 5
Studio apartment 3mins from Carrying Place Golf Club & The Manor. Off HW 400
Coffee/tea maker, fridge, microwave, oven

11. New, Clean and Comfortable Apartment with Private Entrance.

New, Clean and Comfortable Apartment with Private Entrance.
East Gwillimbury
9.0 out of 10, Wonderful, (12 reviews)
"easy to check in and a great place to stay! very helpful hosts."
United States
Kwame A.
The price is ￥16,052
￥25,445 total
includes taxes & fees
Oct 1 - Oct 2
New, Clean and Comfortable Apartment with Private Entrance.
Smart TV, fireplace

12. Modern 5-bedroom house close to Ski and Forest Trails

Modern 5-bedroom house close to Ski and Forest Trails
Ardagh Bluffs
10.0 out of 10, Exceptional, (29 reviews)
"Perfect for a work crew Or a couple families for vacation"
Canada
John V.
The price is ￥45,425
￥84,664 total
includes taxes & fees
Sep 20 - Sep 21
Modern 5-bedroom house close to Ski and Forest Trails
2 bedrooms, iron/ironing board, WiFi, bed sheets

13. Peaceful Rejuvenessence Retreat w/ Spa-Inspired Amenities — Perfect Getaway!

Peaceful Rejuvenessence Retreat w/ Spa-Inspired Amenities — Perfect Getaway!
Georgina
10.0 out of 10, Exceptional, (1 review)
"The amenities of this property were amazing. The outdoor entertainment area with home theatre, hot tub, sauna and peaceful garden was fantastic It was a true gem, happy that I experienced with my family’s This is perfect for couple getaway or a girls trip! Highly recommend!"
Canada
Sorina
The price is ￥30,098
￥41,694 total
includes taxes & fees
Sep 30 - Oct 1
Peaceful Rejuvenessence Retreat w/ Spa-Inspired Amenities — Perfect Getaway!
Game room

14. Lake Simcoe Waterfront Retreat | Private Dock, Sandy Beach & Hot Tub

Lake Simcoe Waterfront Retreat | Private Dock, Sandy Beach & Hot Tub
Georgina
9.8 out of 10, Exceptional, (50 reviews)
"Fabulous location right on the lake with excellent backyard set-up"
Canada
Dwight C.
The price is ￥78,636
￥169,340 total
includes taxes & fees
Sep 24 - Sep 25
Lake Simcoe Waterfront Retreat | Private Dock, Sandy Beach & Hot Tub
Exterior detail

15. The Luxe Haven

The Luxe Haven
East Gwillimbury
The price is ￥8,929
￥40,195 total
includes taxes & fees
Sep 26 - Sep 27
The Luxe Haven
Terrace/patio

16. Spacious | Private | Quiet | 2 BR Walkout Suite

Spacious | Private | Quiet | 2 BR Walkout Suite
Aurora
10.0 out of 10, Exceptional, (1 review)
"This property is an amazing, family-friendly retreat located in a peaceful, quiet neighborhood. The spacious unit is impeccably clean and features a fully equipped kitchen. The host provides outstanding, responsive service, making this an ideal choice for both short-term and long-term stays. Highly recommended."
Canada
Ayla
The price is ￥11,104
￥46,261 total
includes taxes & fees
Sep 28 - Sep 29
Spacious | Private | Quiet | 2 BR Walkout Suite
Exterior

17. Large Estate with Luxury Collection of Amenities

Large Estate with Luxury Collection of Amenities
Schomberg
9.8 out of 10, Exceptional, (49 reviews)
"We enjoyed our stay. The house was very clean and spacious. Every room was nice and the bathrooms were as well. The homeowner was very responsive to our questions."
United States
Dontae R.
The price is ￥269,187
￥401,012 total
includes taxes & fees
Sep 21 - Sep 22
Large Estate with Luxury Collection of Amenities
Terrace/patio

18. Modern 4 Bedroom Townhouse in Barrie South

Modern 4 Bedroom Townhouse in Barrie South
Painswick
9.0 out of 10, Wonderful, (21 reviews)
"Was great!"
Canada
Patrick K.
The price is ￥14,811
￥37,523 total
includes taxes & fees
Sep 23 - Sep 24
Modern 4 Bedroom Townhouse in Barrie South
Smart TV

19. Crazy Farm C-Can Chalet

Crazy Farm C-Can Chalet
Innisfil
8.6 out of 10, Excellent, (4 reviews)
"Hospitality was on key. Enjoyed our stay"
Canada
Hannah
The price is ￥14,491
￥19,902 total
includes taxes & fees
Oct 1 - Oct 2
Crazy Farm C-Can Chalet
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

Comfort Inn & Suites

Comfort Inn & Suites

8/10 Good
"My stay was great, I had higher expectations for the breakfast but it was still good."
Alifonso 1-night trip
Posted 5 hours ago
Comfort Inn & Suites

Find out more about Cookstown

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

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?

Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!: This vacation home near Cookstown is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a hot tub.

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.