Photo by Linda Nisbett

Jacksons Point Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Our top choices for Jacksons Point holiday rentals

9.8 out of 10, Exceptional, (7)
"Great location! Rental was clean and exactly as listed. "
Canada
Laura W.
The price is NZ$453
includes taxes & fees
29 Dec - 30 Dec
5 minutes from the lake! Brand new condo at Jackson's Point, Georgina
2.0 star property
The price is NZ$245
includes taxes & fees
28 Dec - 29 Dec
Spacious 2BR Basement Apt – 5 Mins to Beach
10.0 out of 10, Exceptional, (1)
"The location was perfect for me. The unit was really nice, reminded me of a hotel I stayed at once in NYC. Hostess is supper friendly, quick to respond and was able to accommodate a little request I had. Would stay again. "
Canada
Ashley O.
The price is NZ$291
includes taxes & fees
31 Dec - 1 Jan 2026
Modern comfy brand new basement apartment in a convenient place, pet friendly.
9.0 out of 10, Wonderful, (4)
"Visiting family "
Canada
Elizabeth T.
Friday Harbour, 2BR pet friendly

Holiday Home in Barrie

Cozy house at south end Barrie
9.8 out of 10, Exceptional, (10)
"Excellent, clean property with all the necessary amenities. "
Canada
John
The price is NZ$474
includes taxes & fees
14 Jan - 15 Jan 2026
Cozy house at south end Barrie
8.0 out of 10, Very good, (2)
"The whole setup is very thoughtful and provides a wonderful sheltered camping experience on a private creek. "
Canada
Brett
The price is NZ$270
includes taxes & fees
1 Jan - 2 Jan 2026
The Uxbridge Igloo on Pefferlaw Creek with Private Lake. Pet Friendly!
10.0 out of 10, Exceptional, (6)
"Clean apartment, spacious, nice neighbourhood"
Canada
Peter v.
The price is NZ$285
includes taxes & fees
4 Jan - 5 Jan 2026
New, Clean and Comfortable Apartment with Private Entrance.

Holiday Home in Barrie

The Allandale Residence
10.0 out of 10, Exceptional, (3)
"Clean pet friendly would be pleased to stay again "
Canada
Michael P.
The price is NZ$483
includes taxes & fees
4 Jan - 5 Jan 2026
The Allandale Residence
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 NZ$435
includes taxes & fees
2 Jan - 3 Jan 2026
Modern 4 Bedroom Townhouse in Barrie South
2.0 star property
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 NZ$526
includes taxes & fees
26 Jan - 27 Jan 2026
Oasis Spa w/ Private Sauna!

Holiday Home in Innisfil

Wonderful place of Lake Simkoe
8.8 out of 10, Excellent, (8)
"Nice clean interior with full kitchen and living room space. Very close to Lake Simcoe. Perfect for our brief weekend stay. "
Canada
Jeremy O.
The price is NZ$432
includes taxes & fees
31 Dec - 1 Jan 2026
Wonderful place of Lake Simkoe
2.0 star property
The price is NZ$628
includes taxes & fees
4 Jan - 5 Jan 2026
Lakeside summer retreat at the Venice of Ontario
2.0 star property
10.0 out of 10, Exceptional, (1)
"amazing all around "
Canada
Leshaun W.
The price is NZ$672
includes taxes & fees
5 Jan - 6 Jan 2026
Newly built and perfect for vacations. In the middle of both hwy 400&40

Apartment in Barrie

The Chieftain Suite
9.6 out of 10, Exceptional, (11)
"Thank you for the great accommodations! Bed was super comfortable and location was perfect!"
Canada
Melanie M.
The price is NZ$258
includes taxes & fees
5 Jan - 6 Jan 2026
The Chieftain Suite
10.0 out of 10, Exceptional, (22)
"Homey with ample space. "
United States
Daphne
The price is NZ$629
includes taxes & fees
11 Jan - 12 Jan 2026
Lake Simcoe 4-Bedroom Home 5 Minutes to Beach Park
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 NZ$462
includes taxes & fees
9 Jan - 10 Jan 2026
Central & Cozy 2BR Townhome—Steps to Plaza, 5 Min Drive to Innisfil Beach Park!
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 NZ$566
includes taxes & fees
26 Jan - 27 Jan 2026
Fire & Ice Spa w/ Private Sauna!
10.0 out of 10, Exceptional, (6)
"Beautiful views! The patio is outstanding!"
Canada
Scott E.
The price is NZ$1,285
includes taxes & fees
6 Jan - 7 Jan 2026
Cozy Private Waterfront Cottage at Lake Simcoe

Villa in Simcoe County

Goffatt Island on Lake Simcoe
2.5 star property
The price is NZ$409
includes taxes & fees
1 Jan - 2 Jan 2026
Goffatt Island on Lake Simcoe
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Jacksons Point Hotel Reviews

Find out more about Jacksons Point

Everything you need to know about Jacksons Point 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 Jacksons Point 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 Jacksons Point holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Jacksons Point holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jacksons Point. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jacksons Point 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 Jacksons Point holiday rentals we have selected for you start as low as NZ$258 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Jacksons Point rentals

At Expedia, we put the best Jacksons Point 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 Jacksons Point 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 Jacksons Point 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 Jacksons Point. 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

Can I find a holiday rental in Jacksons Point?

Yes, there are holiday rentals close to the most popular sights in Jacksons Point, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in Jacksons Point. Make sure you have time to check out the spas and bars during your trip.

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

6 Bedroom Executive Cottage near Lake Simcoe & Innisfil Beach Park: This holiday home rental outside of Jacksons Point 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 can I see and do in Jacksons Point?

Lake Simcoe and Bonnie Park are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Sibbald Point Provincial Park and Big Cedar Golf Club.

What are holiday rentals like in Jacksons Point?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Jacksons Point. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for families.