Cookstown Holiday Rentals

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Holiday Rentals in Cookstown

Indoor pool, a heated pool
Luxurious 11-Bedroom Villa with Indoor Pool, Outdoor Sauna & Jacuzzi
10.0 out of 10, Exceptional, (1)
"We had a small wedding and we absolutely loved being able to use the beautiful grounds for the ceremony and also being able to enjoy the spa for the rest of the weekend. We couldn’t have asked for a better location."
The price is NZ$2,188
per night
20 May - 21 May
Luxurious 11-Bedroom Villa with Indoor Pool, Outdoor Sauna & Jacuzzi
Exterior
Paradise Suites - Peaceful Getaway
10.0 out of 10, Exceptional, (3)
"We enjoyed this house very much. House was very clean and well furnished. I highly recommend this house."
The price is NZ$1,211
per night
16 May - 17 May
Paradise Suites - Peaceful Getaway
Interior
Lake Simicoe Renovated Spacious 2-Storey Vacation home near Innisfil Beach Park
10.0 out of 10, Exceptional, (4)
"The property was clean and the same as shown in the pictures, the host was amazing and accommodative, responses were very quick. We all had a wonderful time, thank you so much!"
The price is NZ$670
per night
21 May - 22 May
Lake Simicoe Renovated Spacious 2-Storey Vacation home near Innisfil Beach Park
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Exterior
The Mansion, Wasaga beach, Blue mountain
10.0 out of 10, Exceptional, (2)
"Wali was an amazing host. Gave us a tour of the place when we got there to make sure we are comfortable. Would 100% book this place for our parents to come and enjoy in the summer time."
The price is NZ$3,024
per night
20 May - 21 May
The Mansion, Wasaga beach, Blue mountain
Living area
Experience luxury living at FH only a 10-min drive from South Barry Go Station
10.0 out of 10, Exceptional, (2)
"Love the marina area and the quiet location of this unit. Very clean and well appointed unit! With all of the small stuff and amenities in it, that someone can forget to bring! Great walking paths, restaraunts a short walk away. Great place to relax."
The price is NZ$406
per night
22 May - 23 May
Experience luxury living at FH only a 10-min drive from South Barry Go Station
Property grounds
Cute family cottage getaway near Lake Simcoe!
10.0 out of 10, Exceptional, (5)
"We spent a week at this cottage with my family, my brother and his daughter, and my parents. The cottage was easy to find and is close to local grocery stores, restaurants, hardware stores, etc. The beach is about a 12 minute walk, but the hosts provide a parking pass for the parking lot at the beach, which is convenient. The cottage itself had the basics you'll need, and the full kitchen was great as we prefer to eat in. The backyard was great to spread out in and we used the fire pit most...
Cute family cottage getaway near Lake Simcoe!
Fridge, microwave, oven, stovetop
Large Estate with Luxury Collection of Amenities
10.0 out of 10, Exceptional, (43)
"The house was fantastic. I think better pillows would be in order. A little too many rules but under the circumstances it sleeps 16. We had a wonderful time for a family reunion"
The price is NZ$3,597
per night
20 May - 21 May
Large Estate with Luxury Collection of Amenities
View from property
Friday Harbour Resort
4.0 star property
10.0 out of 10, Exceptional, (1)
"Great layout with three bedrooms, each with their own bathrooms, plus a guest bathroom on the main floor. The kitchen/dinning area was great and well equipped."
Friday Harbour Resort
Outdoor dining
Exclusive Lakefront House on Private Lake
10.0 out of 10, Exceptional, (7)
"We loved the house at Little Lake! Right on the water and just a couple minutes drive from everything you could possibly need. You feel like you are in cottage country in the city! We had a really great stay and would love to come back ;-)"
Exclusive Lakefront House on Private Lake
Exterior
Chic home 3 BR & Office, backyard Oasis with kids playground, near Canal & lake.
10.0 out of 10, Exceptional, (2)
"Our group was staying for a wedding nearby. Raj and Sophie take great care of the home and it was well stocked with everything we needed! Highly recommended. "
Chic home 3 BR & Office, backyard Oasis with kids playground, near Canal & lake.
Living area
6 Bedroom Executive Cottage near Innisfil Beach - Special Winter Discount 20-35%
9.8 out of 10, Exceptional, (54)
"Great place and great host"
6 Bedroom Executive Cottage near Innisfil Beach - Special Winter Discount 20-35%
Exterior
Romantic Log Cabin in the Woods - Hot Tub under the Stars -80 km's from CN Tower
9.8 out of 10, Exceptional, (72)
"Had a great weekend for my Birthday! My dogs both loved the cabin and wooded trails."
Romantic Log Cabin in the Woods - Hot Tub under the Stars -80 km's from CN Tower
Property grounds
A Gorgeous Victorian Country Style Farm Stay!
9.8 out of 10, Exceptional, (6)
"Wonderful hosts with a large and comforting amenities"
A Gorgeous Victorian Country Style Farm Stay!
Property grounds
Lake Simcoe LakeHouse-S/W Exposure! Hot Tub, Sandy Water, Game Rm!
9.8 out of 10, Exceptional, (29)
"Was a great location. Host was very responsive and provided all the information we needed. House was perfect for 6 couples."
Lake Simcoe LakeHouse-S/W Exposure! Hot Tub, Sandy Water, Game Rm!
Property grounds
PRIVATE RESORT COTTAGE POOL SPA HOT TUB SAUNA 20 Acres of Wooded GRASSLAND
9.6 out of 10, Exceptional, (4)
"Amazing place, tons of space, good get away location with everything you need!"
PRIVATE RESORT COTTAGE POOL SPA HOT TUB SAUNA 20 Acres of Wooded GRASSLAND
Fridge, cookware/dishes/utensils, dining tables
Private recreational basement in Holland Landing
9.6 out of 10, Exceptional, (5)
"Hosted birthday party here, best birthday party in this incredible house. There was board games, speaker foosball, dart board. It was well furnished spacious house. Liked every bit of stay! Thank you ! Host!!"
The price is NZ$236
per night
22 May - 23 May
Private recreational basement in Holland Landing
Interior
Vacation Escape ~Sauna~Fireplace ~BBQ~ Outdoor Fire-pit ~Ping pong
9.4 out of 10, Exceptional, (9)
"This was the perfect place for our semi-annual Girls chill weekend! Natalya was an excellent host and responded timely to all inquiries. You will 100% enjoy your stay here! Also, we happened to visit during a spring snow storm but the area is stunning no matter what time of year you choose to visit!"
Vacation Escape ~Sauna~Fireplace ~BBQ~ Outdoor Fire-pit ~Ping pong
Premium Apartment, 1 Queen Bed, Non Smoking, City View | Private kitchen
Parkside House
3.5 star property
9.4 out of 10, Exceptional, (222)
"We loved the place and look forward to staying again - hopefully for more than an evening next time. "
The price is NZ$164
per night
22 May - 23 May
Parkside House
Property grounds
Beautiful, Warm and Cozy Home in Richmond Hill
9.4 out of 10, Exceptional, (13)
"Nice property - quiet family neighborhood."
Beautiful, Warm and Cozy Home in Richmond Hill
Property grounds
Friday Harbour Resort on Lake Simcoe
9.2 out of 10, Wonderful, (14)
"This property was perfect for myself and my children it was clean it was about 10 to 15 minutes to get to the beach which we enjoyed walking to every day. All amenities were close by. The apartment has everything you need. I don't think I contacted the host once, it just wasn't necessary. So if you are looking for a safe clean practically situated Condo this is perfect. 👌🏼 Thank you"
Friday Harbour Resort on Lake Simcoe
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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.

Other types of properties in Cookstown you may be interested in

Property grounds
PRIVATE RESORT COTTAGE POOL SPA HOT TUB SAUNA 20 Acres of Wooded GRASSLAND
9.6 out of 10, Exceptional, (4)
"Amazing place, tons of space, good get away location with everything you need!"
PRIVATE RESORT COTTAGE POOL SPA HOT TUB SAUNA 20 Acres of Wooded GRASSLAND
King Suite with Jetted Tub
Monte Carlo Inn Barrie Suites
3.0 star property
8.0 out of 10, Very good, (1497)
"Great location, room was great 👍"
The price is NZ$160
per night
9 Jun - 10 Jun
Monte Carlo Inn Barrie Suites
Standard Room, 2 Queen Beds
Super 8 by Wyndham Barrie South
7.6 out of 10, Good, (1049)
"Comp breakfast was delicious! Friendly check in and room was clean and comfy. "
The price is NZ$105
per night
2 Jun - 3 Jun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cookstown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cookstown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Cookstown. Seeing all the best attractions is bound to make you fall in love with Cookstown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Cookstown short-term rentals, that won’t be hard to do.

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’s there to see and do in Cookstown?

Explore the area and family-friendly sights such as Holland Marsh, or get out into nature at a spot like Barrie Centennial 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.

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