A lighthouse on a rocky breakwater extending into a calm body of water, with a forested shoreline and a partly cloudy sky in the background.

Jacksons Point Vacation Rentals

Dates

November 2026

December 2026

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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

Georgina

Jeff

CA $340 total

includes taxes & fees

Nov 10 - Nov 11

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

Sutton

Brodie V.

CA $321 total

includes taxes & fees

Nov 11 - Nov 12

A modern interior with a kitchen, dining area, and living room.

3. Cozy 3BR Cottage Near Lake Simcoe

Georgina

Corinne

CA $174 total

includes taxes & fees

Nov 30 - Dec 1

4. Friday Harbour Resort 2 Bedroom Pool Lake Simcoe

Innisfil

Albert M.

CA $258 total

includes taxes & fees

Nov 9 - Nov 10

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

Innisfil

Hannah

CA $146 total

includes taxes & fees

Nov 24 - Nov 25

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

Innisfil

lisa

CA $286 total

includes taxes & fees

Nov 9 - Nov 10

7. Cozy 3BR Cottage Near Lake Simcoe

Georgina

CA $171 total

includes taxes & fees

Nov 30 - Dec 1

A modern hotel with a rooftop pool and outdoor seating area.

8. Upscale Spa Getaway w/ Private Sauna

Innisfil

CA $368 total

includes taxes & fees

Nov 9 - Nov 10

A glass table with a champagne bucket and glasses on a balcony with string lights.

9. Fire & Ice Spa w/ Private Sauna!

Innisfil

Craig

CA $397 total

includes taxes & fees

Nov 9 - Nov 10

A beach with a blue mat leading to the water, clear skies, and a distant pier.

10. ARCA Cozy Cabin-Innisfil Beach

Innisfil

Daisy G.

CA $368 total

includes taxes & fees

Nov 29 - Nov 30

A marina at dusk with boats docked, waterfront buildings, and a calm water surface reflecting the lights.

11. Oasis Spa w/ Private Sauna!

Innisfil

"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....

Matthew K.

CA $358 total

includes taxes & fees

Nov 9 - Nov 10

A marina with boats docked, a clear blue sky, and a view of buildings in the distance.

12. FRIDAY HARBOUR CHIC WATERFRONT GETAWAY

Innisfil

Elias

CA $306 total

includes taxes & fees

Nov 9 - Nov 10

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!

Innisfil

Dragisa

CA $435 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with dark cabinets, a stainless steel oven, and a granite countertop.

14. Innisfil Getaway

Innisfil

CA $368 total

includes taxes & fees

Nov 9 - Nov 10

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!

Innisfil

Ashna

CA $354 total

includes taxes & fees

Nov 9 - Nov 10

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

Innisfil

CA $323 total

includes taxes & fees

Nov 15 - Nov 16

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.

Beaverton

Ginelle M.

CA $565 total

includes taxes & fees

Nov 9 - Nov 10

A wicker basket with ceramic animal figurines and a vase of white flowers on a wooden table.

18. Utopia villa and spa

Innisfil

Krista K.

CA $638 total

includes taxes & fees

Nov 9 - Nov 10

A clear river with visible rocks and trees on the banks.

19. Cozy Cottage Across Lake Simcoe

Innisfil

Michael P.

CA $528 total

includes taxes & fees

Dec 1 - Dec 2

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

Painswick

Patrick K.

CA $308 total

includes taxes & fees

Nov 10 - Nov 11

View all properties

Find vacation rentals that suit your style

Top Jacksons Point Hotel Reviews

A building with a brick facade, a black door with a window, and a flower bed with various flowers.

SHORE VISTA LODGE

Georgina

10/10 Excellent

Jakob

A large, historic building with a prominent tower, a covered porch, and a well-lit entrance.

The Briars Resort & Spa

Georgina

10/10 Excellent

Anonymous traveller

An outdoor seating area with a fire pit, yellow chairs, and a striped sofa.

Home2 Suites By Hilton Barrie

Barrie

10/10 Excellent

julie

A lobby with a reception desk, a blue sofa, and yellow armchairs.

Comfort Inn & Suites

Bradford

10/10 Excellent

Brenda

Cozy 3BR Cottage Near Lake Simcoe

Georgina

10/10 Excellent

Corinne

A large, single-story building with a green roof, surrounded by lush greenery and a small parking area.

Lakeside Inn

Ramara

10/10 Excellent

It was excellent and the beach across the street excellent view from my room perfect for a photographer and beach bum..loads of beaching swimming and photos. Lots of birds beach sunsets are amazing for photography and everything is fairly close for eating and outdoor activities for those who like to walk hike or bike. Even a hammock across the street by their dock for a leisurely rest...loved it. The property owners manage the Inn as well a lovely young couple very up beat and helpful. They have...

sandra

A hotel room with a sofa, a small round table, a lamp, and a bed in the background.

Comfort Inn & Suites Barrie - Highway 400

Allandale

10/10 Excellent

Alain

A modern lobby with a blue sofa, a round table, and a stone accent wall.

Fairfield Inn & Suites by Marriott Barrie

Ardagh Bluffs

10/10 Excellent

We recently travelled to Barrie for a medical procedure and the Barrie Fairfield was a great choice for our stay. While there are not a lot of amenities in the neighbourhood the proximity to Hwy 400 is very convenient and there are lots of restaurants a 5-10 minute drive away. The staff were exceptionally courteous and helpful and our room was super-clean and comfortable. We would definitely stay here again.

Anonymous traveller

Quality Inn

Barrie

10/10 Excellent

Kay

A spacious bathroom with a large bathtub, a wooden vanity, and a fireplace.

Monte Carlo Inn Barrie Suites

Barrie

10/10 Excellent

Travelodge by Wyndham Barrie

Barrie

10/10 Excellent

Jeremy

A hotel room with a bathtub, two armchairs, a bed with a headboard, a nightstand, and a lamp.

Super 8 by Wyndham Barrie South

Barrie

10/10 Excellent

Haley

A spacious living area with a stone fireplace, comfortable seating, and a kitchen in the background.

Comfort Inn Newmarket - Aurora

Newmarket

10/10 Excellent

Josh

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jacksons Point vacation rentals we have selected for you start as low as CA $90 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 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.

Jacksons Point Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Jacksons Point vacation rentals

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

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

3. Cozy 3BR Cottage Near Lake Simcoe

4. Friday Harbour Resort 2 Bedroom Pool Lake Simcoe

5. Crazy Farm C-Can Chalet

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

7. Cozy 3BR Cottage Near Lake Simcoe

8. Upscale Spa Getaway w/ Private Sauna

9. Fire & Ice Spa w/ Private Sauna!

10. ARCA Cozy Cabin-Innisfil Beach

11. Oasis Spa w/ Private Sauna!

12. FRIDAY HARBOUR CHIC WATERFRONT GETAWAY

13. Luxury Beach Spa w/ Private Sauna!

14. Innisfil Getaway

15. Lakehouse Peaceful Cottage Modern Retreat - Pet Friendly!

16. Luxury 2BD Condo Friday Harbour Resort

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

18. Utopia villa and spa

19. Cozy Cottage Across Lake Simcoe

20. Modern 4 Bedroom Townhouse in Barrie South

Find vacation rentals that suit your style

Top Jacksons Point Hotel Reviews

SHORE VISTA LODGE

10/10 Excellent

Find out more about Jacksons Point

Jacksons Point vacation rentals: An excellent choice for every season

How to find incredible deals on Jacksons Point rentals

Explore a world of travel with Expedia