Cookstown Holiday Rentals

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Holiday Rentals in Cookstown

Our top choices for Cookstown holiday rentals

Residence & Conference Centre - Barrie

2.0 star property
7.2 out of 10, Good, (716)
"Stayed in a 2 bedroom suite, it was perfect for our needs and very afforable. Would stay here again for sure. "
Residence & Conference Centre - Barrie

Residence & Conference Centre - King City

2.0 star property
8.4 out of 10, Very good, (506)
"I really enjoy staying there."
Residence & Conference Centre - King City

Parkside House

3.5 star property
9.4 out of 10, Exceptional, (312)
"Great walking location to downtown "
The price is AU$185
includes taxes & fees
1 Sept - 2 Sept
Parkside House

Luxury 3BR Villa

2.0 star property
The price is AU$9,330
includes taxes & fees
2 Sept - 3 Sept
Luxury 3BR Villa

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 AU$652
includes taxes & fees
1 Sept - 2 Sept
4 Bedroom Cottage #2: Innisfil Resort

Cozy 2BR Highpoint located at the Friday Harbour

9.4 out of 10, Exceptional, (16)
"Wonderful area and host was very helpful "
Cozy 2BR Highpoint located at the Friday Harbour

Adorable waterfront escape

The price is AU$432
includes taxes & fees
1 Oct - 2 Oct
Adorable waterfront escape

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!

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

Rustic Retreat: Spacious Cottage with Private Saltwater Pool and Sauna

Rustic Retreat: Spacious Cottage with Private Saltwater Pool and Sauna

Sunny Side Retreat

2.0 star property
Sunny Side Retreat

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 AU$598
includes taxes & fees
1 Sept - 2 Sept
5br 3.5bth home w Free Parkings+Ensuite laundry Barrie,ON

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

9.6 out of 10, Exceptional, (121)
"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

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

8.6 out of 10, Excellent, (7)
"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 AU$895
includes taxes & fees
1 Sept - 2 Sept
Welcome to our luxurious villa in the heart of downtown Newmarket!

6BR Waterfront Private Beach · Hot Tub · Sunset Deck · 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 "
6BR Waterfront Private Beach · Hot Tub · Sunset Deck · Lake Simcoe

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 AU$334
includes taxes & fees
2 Sept - 3 Sept
Chic Staycation Condo at FH

Friday Harbour Resort on Lake Simcoe

9.2 out of 10, Wonderful, (14)
"We have really enjoyed our stay."
Friday Harbour Resort on Lake Simcoe

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 AU$2,071
includes taxes & fees
4 Sept - 5 Sept
Lake Simcoe Waterfront Villa | Walk to lake · Free canoes · BBQ & firepit

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 AU$244
includes taxes & fees
13 Sept - 14 Sept
Studio apartment 3mins from Carrying Place Golf Club & The Manor. Off HW 400

Large Estate with Luxury Collection of Amenities

9.8 out of 10, Exceptional, (48)
"Everything that we needed for a great getaway was available! The house was clean, spacious and the host was very accommodating. We spent most of our time on site in the pool and hot tub. And our group of 14 enjoyed every moment!"
The price is AU$4,048
includes taxes & fees
3 Sept - 4 Sept
Large Estate with Luxury Collection of Amenities
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

Find out more about Cookstown

Find out more about Cookstown

Everything you need to know about Cookstown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cookstown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cookstown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cookstown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cookstown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cookstown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cookstown holiday rentals we have selected for you start as low as AU$185 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cookstown rentals

At Expedia, we put the best Cookstown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cookstown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cookstown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cookstown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!: This holiday home rental outside of Cookstown is located on the beach, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 1 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 Claredon Beach 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.