Cookstown Vacation Rentals

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Sep 26 - Sep 27
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Oct 3 - Oct 5

Vacation Rentals in Cookstown

Residence & Conference Centre - Barrie
Balcony

Residence & Conference Centre - Barrie

2.0 star property
7.2 out of 10, Good, (722)
"Great place "
Residence & Conference Centre - Barrie
Residence & Conference Centre - King City
Terrace/patio

Residence & Conference Centre - King City

2.0 star property
8.4 out of 10, Very Good, (509)
"I really enjoy staying there."
Residence & Conference Centre - King City
Parkside House
Premium Apartment, 1 Queen Bed, Non Smoking, City View | Private kitchen | Fridge, microwave, coffee/tea maker, electric kettle

Parkside House

3.5 star property
9.4 out of 10, Exceptional, (314)
"Great walking location to downtown "
Parkside House
Luxury 3BR Villa
House | Private kitchen

Luxury 3BR Villa

2.0 star property
The price is ￥722,895
￥897,954 total
includes taxes & fees
Oct 9 - Oct 10
Luxury 3BR Villa
4 Bedroom Cottage #2: Innisfil Resort
Exterior

4 Bedroom Cottage #2: Innisfil Resort

2.0 out of 10, (1)
"We were not able to stay on the cottage. It was messy and uncleaned when we came. Host is not answering. Expedia is also not too helpful with our experience. "
The price is ￥37,376
￥62,082 total
includes taxes & fees
Sep 27 - Sep 28
4 Bedroom Cottage #2: Innisfil Resort
Cozy 2BR Highpoint located at the Friday Harbour
Marina

Cozy 2BR Highpoint located at the Friday Harbour

9.0 out of 10, Wonderful, (19)
"Wonderful area and host was very helpful "
Cozy 2BR Highpoint located at the Friday Harbour
Chic Staycation Condo at FH
Private kitchen

Chic Staycation Condo at FH

7.8 out of 10, Good, (10)
"Amazing stay! It was very beautiful and the place was kept very clean. Had a balcony with seating. Really close walking distance to the boardwalk. Just bring your own shower amenities (ex; body wash)"
The price is ￥13,963
￥31,921 total
includes taxes & fees
Oct 4 - Oct 5
Chic Staycation Condo at FH
Vacation Home on Simcoe lake
Beach

Vacation Home on Simcoe lake

2.0 out of 10, (1)
"The owner had removed the property and we apparently booked with some kind of zombie account. VRBO had not validated the listing but kept communicating everything was good to go. VRBO did book our party of nine hotel rooms. These were over a half hour from the property and no where near the beach. We had no facility to prepare the food we had brought and were forced to eat at restaurants the whole weekend. VRBO did ensure the accomodation was financially neutral, but it was still, overall, a...
Vacation Home on Simcoe lake
Luxury Lakehouse · 6BR · Private Sandy Beach · Hot Tub · Sunset View Lake Simcoe
Dining

Luxury Lakehouse · 6BR · Private Sandy Beach · Hot Tub · Sunset View Lake Simcoe

10.0 out of 10, Exceptional, (41)
"Excellent property to stay at!!! The host went above expectations with the little things Would definitely stay there again Thank you "
Luxury Lakehouse · 6BR · Private Sandy Beach · Hot Tub · Sunset View Lake Simcoe
5br 3.5bth home w Free Parkings+Ensuite laundry Barrie,ON
Exterior detail

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

9.6 out of 10, Exceptional, (5)
"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 ￥18,313
￥56,878 total
includes taxes & fees
Oct 1 - Oct 2
5br 3.5bth home w Free Parkings+Ensuite laundry Barrie,ON
Sunny Side Retreat
Exterior

Sunny Side Retreat

2.0 star property
Sunny Side Retreat
Rustic Retreat: Spacious Cottage with Private Saltwater Pool and Sauna
Outdoor pool, a heated pool

Rustic Retreat: Spacious Cottage with Private Saltwater Pool and Sauna

Rustic Retreat: Spacious Cottage with Private Saltwater Pool and Sauna
COZY COTTAGE WALKING DISTANCE TO LAKE SIMCOE & FRIDAY HARBOUR
Beach

COZY COTTAGE WALKING DISTANCE TO LAKE SIMCOE & FRIDAY HARBOUR

9.2 out of 10, Wonderful, (49)
"Great time as always!"
COZY COTTAGE WALKING DISTANCE TO LAKE SIMCOE & FRIDAY HARBOUR
Romantic Log Cabin in the Woods - Hot Tub under the Stars -80 km's from CN Tower
Exterior

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

9.6 out of 10, Exceptional, (123)
"Marie was wonderful and the visit with the horses was my highlight. The cabin was gorgeous, clean, and quiet. The morning coffee was very much appreciated. Skylight was so nice at night to see stars. Communication was great. 10/10 recommend."
Romantic Log Cabin in the Woods - Hot Tub under the Stars -80 km's from CN Tower
Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (79)
"Great stay. Excellent location and beautiful outdoor area."
Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!
Adorable waterfront escape
Terrace/patio

Adorable waterfront escape

8.0 out of 10, Very Good, (1)
"Very nice stay."
The price is ￥19,181
￥45,515 total
includes taxes & fees
Sep 30 - Oct 1
Adorable waterfront escape
Welcome to our luxurious villa in the heart of downtown Newmarket!
Exterior

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

8.6 out of 10, Excellent, (8)
"Great location and a beautiful house. Very spacious and everything I needed for my stay was there. I will book here again if I ever need to be in the area."
The price is ￥48,193
￥84,713 total
includes taxes & fees
Sep 28 - Sep 29
Welcome to our luxurious villa in the heart of downtown Newmarket!
The Mansion, Wasaga beach, Blue mountain
Exterior

The Mansion, Wasaga beach, Blue mountain

10.0 out of 10, Exceptional, (4)
"Beautiful view fun experience"
The price is ￥148,434
￥245,908 total
includes taxes & fees
Oct 9 - Oct 10
The Mansion, Wasaga beach, Blue mountain
3 Bedrooms Cottage W LAKE VIEWS, beside waterfront trail and steps from beach
Terrace/patio

3 Bedrooms Cottage W LAKE VIEWS, beside waterfront trail and steps from beach

9.4 out of 10, Exceptional, (6)
"Great house, nice sized bedrooms, beautiful views of Lake. Great location for an adult family."
3 Bedrooms Cottage W LAKE VIEWS, beside waterfront trail and steps from beach
Studio apartment 3mins from Carrying Place Golf Club & The Manor. Off HW 400
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (1)
"Nice place"
The price is ￥10,174
￥20,936 total
includes taxes & fees
Oct 1 - Oct 2
Studio apartment 3mins from Carrying Place Golf Club & The Manor. Off HW 400
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

Travelodge by Wyndham Barrie

Travelodge by Wyndham Barrie

10/10 Excellent
"No elevator for those of us with bad feet !"
Bob 1-night trip
Posted 1 day ago
Travelodge by Wyndham Barrie

Find out more about Cookstown

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!

Explore a world of travel with Expedia

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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?

Luxury 3BR Villa: You might like this vacation home rental near Cookstown. It comes with WiFi so you can feel at home during your trip.

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 Claredon Beach Park. 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.