Jacksons Point Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Jacksons Point vacation rentals

A multi-story building with a stone facade and multiple windows.

1. 5 minutes from the lake! Brand new condo at Jackson's Point, Georgina

5 minutes from the lake! Brand new condo at Jackson's Point, Georgina
Georgina
9.8 out of 10, Exceptional, (7 reviews)
"Excellent property close to our event and family. Really enjoyed our stay. "
Canada
Jeff
$217 nightly
The price is $245
Nov 10 - Nov 11
Total with taxes and fees
5 minutes from the lake! Brand new condo at Jackson's Point, Georgina
A wooden cabin with a porch, surrounded by snow and trees.

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

Romantic Log Cabin in the Woods - Hot Tub under the Stars -80 km's from CN Tower
Sutton
9.6 out of 10, Exceptional, (159 reviews)
"Great little cabin! Very private and cozy. Zero issues during our stay and very reasonable price."
United States
Brodie V.
$221 nightly
The price is $250
Nov 11 - Nov 12
Total with taxes and fees
Romantic Log Cabin in the Woods - Hot Tub under the Stars -80 km's from CN Tower
A modern interior with a kitchen, dining area, and living room.

3. Cozy 3BR Cottage Near Lake Simcoe

Cozy 3BR Cottage Near Lake Simcoe
2.0 star property
Georgina
8.0 out of 10, Very good, (5 reviews)
"It was comfortable and cozy felt like home. Alot of beaches ,trails and shopping around."
Canada
Corinne
$110 nightly
The price is $124
Nov 30 - Dec 1
Total with taxes and fees
Cozy 3BR Cottage Near Lake Simcoe
Marina

4. Friday Harbour Resort 2 Bedroom Pool Lake Simcoe

Friday Harbour Resort 2 Bedroom Pool Lake Simcoe
Innisfil
9.4 out of 10, Exceptional, (13 reviews)
"Check-in was easy, the apartment was clean and well equipped. Would stay again."
Canada
Albert M.
$163 nightly
The price is $184
Nov 8 - Nov 9
Total with taxes and fees
Friday Harbour Resort 2 Bedroom Pool Lake Simcoe
A cozy living room with a brown sofa, a coffee table, and a TV. There's a kitchen area with a fridge and a sink in the background.

5. Crazy Farm C-Can Chalet

Crazy Farm C-Can Chalet
Innisfil
8.8 out of 10, Excellent, (6 reviews)
"Hospitality was on key. Enjoyed our stay"
Canada
Hannah
$92 nightly
The price is $104
Nov 24 - Nov 25
Total with taxes and fees
Crazy Farm C-Can Chalet
A modern living room with a TV, a round coffee table, a sofa, and a view of a cityscape through large windows.

6. Stunning 1BR w Pool ~ Free Parking & Self Check-In

Stunning 1BR w Pool ~ Free Parking & Self Check-In
Innisfil
10.0 out of 10, Exceptional, (5 reviews)
"Although our stay was short, we had a wonderful experience. The host was excellent at communicating and made everything easy and seamless. The place was very clean, comfortable, and easily accessible. We really enjoyed our stay and would definitely love to come back!"
Canada
lisa
$183 nightly
The price is $206
Nov 9 - Nov 10
Total with taxes and fees
Stunning 1BR w Pool ~ Free Parking & Self Check-In
A modern interior with a kitchen, dining area, and living room.

7. Cozy 3BR Cottage Near Lake Simcoe

Cozy 3BR Cottage Near Lake Simcoe
Georgina
$122 nightly
The price is $122
Nov 30 - Dec 1
Total with taxes and fees
Cozy 3BR Cottage Near Lake Simcoe
A modern hotel with a rooftop pool and outdoor seating area.

8. Upscale Spa Getaway w/ Private Sauna

Upscale Spa Getaway w/ Private Sauna
Innisfil
$243 nightly
The price is $263
Nov 8 - Nov 9
Total with taxes and fees
Upscale Spa Getaway w/ Private Sauna
A glass table with a champagne bucket and glasses on a balcony with string lights.

9. Fire & Ice Spa w/ Private Sauna!

Fire & Ice Spa w/ Private Sauna!
Innisfil
10.0 out of 10, Exceptional, (13 reviews)
"Great views in a warm, fire-lit setting—perfect spot for a night out."
Canada
Craig
$263 nightly
The price is $283
Nov 8 - Nov 9
Total with taxes and fees
Fire & Ice Spa w/ Private Sauna!
A beach with a blue mat leading to the water, clear skies, and a distant pier.

10. ARCA Cozy Cabin-Innisfil Beach

ARCA Cozy Cabin-Innisfil Beach
Innisfil
9.4 out of 10, Exceptional, (18 reviews)
"Our family of 4 really enjoyed our stay! It's a short walk or drive to a private beach. We loved watching the ducks and geese on the water. Wifi worked well and the cabin was well stocked with cooking utensils. I would recommend!"
United States
Joanna H.
$231 nightly
The price is $261
Nov 29 - Nov 30
Total with taxes and fees
ARCA Cozy Cabin-Innisfil Beach
A marina at dusk with boats docked, waterfront buildings, and a calm water surface reflecting the lights.

11. Oasis Spa w/ Private Sauna!

Oasis Spa w/ Private Sauna!
Innisfil
10.0 out of 10, Exceptional, (1 review)
"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.
$236 nightly
The price is $255
Nov 7 - Nov 8
Total with taxes and fees
Oasis Spa w/ Private Sauna!
A marina with boats docked, a clear blue sky, and a view of buildings in the distance.

12. FRIDAY HARBOUR CHIC WATERFRONT GETAWAY

FRIDAY HARBOUR CHIC WATERFRONT GETAWAY
Innisfil
9.6 out of 10, Exceptional, (7 reviews)
"Cozy space, large washroom, kitchen, perfect location!"
Canada
Elias
$195 nightly
The price is $221
Nov 8 - Nov 9
Total with taxes and fees
FRIDAY HARBOUR CHIC WATERFRONT GETAWAY
A night scene with a fire feature, a bottle of champagne, and a starry sky visible through a glass enclosure.

13. Luxury Beach Spa w/ Private Sauna!

Luxury Beach Spa w/ Private Sauna!
Innisfil
9.8 out of 10, Exceptional, (7 reviews)
"We just wanted to get out of town and enjoy some peaceful and relaxing time away, and that’s exactly what we got. "
Canada
Dragisa
$288 nightly
The price is $311
Nov 7 - Nov 8
Total with taxes and fees
Luxury Beach Spa w/ Private Sauna!
A modern kitchen with dark cabinets, a stainless steel oven, and a granite countertop.

14. Innisfil Getaway

Innisfil Getaway
Innisfil
$222 nightly
The price is $251
Nov 16 - Nov 17
Total with taxes and fees
Innisfil Getaway
A living room with a white sofa, a coffee table with a glass bowl, and a flat-screen TV on a stand.

15. Lakehouse Peaceful Cottage Modern Retreat - Pet Friendly!

Lakehouse Peaceful Cottage Modern Retreat - Pet Friendly!
Innisfil
6.0 out of 10, (3 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
$223 nightly
The price is $252
Nov 9 - Nov 10
Total with taxes and fees
Lakehouse Peaceful Cottage Modern Retreat - Pet Friendly!
A marina with multiple boats docked, surrounded by modern buildings with a mix of commercial and residential spaces.

16. Luxury 2BD Condo Friday Harbour Resort

Luxury 2BD Condo Friday Harbour Resort
Innisfil
$204 nightly
The price is $231
Nov 15 - Nov 16
Total with taxes and fees
Luxury 2BD Condo Friday Harbour Resort
A deck with a view of the sea and sunset.

17. Lakefront Cottage w/Hot Tub, BBQ Grill, Deck, Fire Pit, Fire Place, Sauna, Dock.

Lakefront Cottage w/Hot Tub, BBQ Grill, Deck, Fire Pit, Fire Place, Sauna, Dock.
Beaverton
9.2 out of 10, Wonderful, (96 reviews)
"Great cottage and the water was beautiful. Would recommend for families with kids."
United States
Ginelle M.
$356 nightly
The price is $402
Nov 8 - Nov 9
Total with taxes and fees
Lakefront Cottage w/Hot Tub, BBQ Grill, Deck, Fire Pit, Fire Place, Sauna, Dock.
A wicker basket with ceramic animal figurines and a vase of white flowers on a wooden table.

18. Utopia villa and spa

Utopia villa and spa
Innisfil
10.0 out of 10, Exceptional, (11 reviews)
"The hosts were very accommodating and communication was good. The outside of the property is VERY deceiving but once inside it is beautiful and very cozy."
Canada
Krista K.
$403 nightly
The price is $455
Nov 9 - Nov 10
Total with taxes and fees
Utopia villa and spa
A clear river with visible rocks and trees on the banks.

19. Cozy Cottage Across Lake Simcoe

Cozy Cottage Across Lake Simcoe
Innisfil
8.4 out of 10, Very good, (13 reviews)
"Excellent location"
Canada
Michael P.
$333 nightly
The price is $376
Dec 1 - Dec 2
Total with taxes and fees
Cozy Cottage Across Lake Simcoe
A brick exterior with a glass door and a small outdoor seating area with a table and chairs.

20. 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.
$195 nightly
The price is $221
Nov 10 - Nov 11
Total with taxes and fees
Modern 4 Bedroom Townhouse in 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.
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Top Jacksons Point Hotel Reviews

An indoor swimming pool with clear lane markings, a wooden ceiling, and large windows.
Ramada by Wyndham Jacksons Point

Ramada by Wyndham Jacksons Point

Ramada by Wyndham Jacksons Point
Georgina

10/10 Excellent

Great place to enjoy with friends or family.
United States
Pedro
Reviewed May 9, 2025
Ramada by Wyndham Jacksons Point

Find out more about Jacksons Point

Everything you need to know about Jacksons Point vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Jacksons Point vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Jacksons Point vacation 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 low season months. For more hustle and bustle, you may prefer to visit Jacksons Point in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $103 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Jacksons Point rentals

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

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 vacation rental in Jacksons Point?

Yes, we have vacation rentals close to top attractions in Jacksons Point, or you can select a 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's the top vacation rental in Jacksons Point?

Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!: This vacation home rental near Jacksons Point 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 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 larger area, you’ll find Sibbald Point Provincial Park and Lyndhurst Golf Club.

What are vacation rentals like in Jacksons Point?

Vacation rentals are private properties you can stay in for several days or longer in Jacksons Point. Vacation rentals feature extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a small group gathering.

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