Jacksons Point Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

64 Houses

10

Rainbow-bow

Georgina / Jacksons Point

Jacksons Point cottage

3 2 1 night min

  • 3 bedrooms
  • sleeps 2
  • 1 night min
  • Child Friendly

Price per night from

$172

Price per night from

$172

(1) Excellent 

13

Lake Simcoe-- Jacksons Pt

Georgina / Jacksons Point

Jacksons Point cottage

6 10 3 nights min

  • 6 bedrooms
  • sleeps 10
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$259

Price per night from

$259

49

Classy Homestyle Cottage (Lake Simcoe)

Georgina / Jacksons Point

Jacksons Point cottage

4 13 1 night min

  • 4 bedrooms
  • sleeps 13
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$166

Price per night from

$166

10

Georgian Country Guesthouse minutes to Lake Simcoe

Georgina / Jacksons Point

Jacksons Point guest house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

Price per night from

$91

Price per night from

$91

Great rentals within 20 miles that match your search

Distance approx 16.02 km from Jacksons Point

(1) Excellent 

39

Trendi Suites "The Island"

Ontario / Barrie

Barrie house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 2 mi
  • Child Friendly
  • Private garden

Price per night from

$134

Price per night from

$134

Distance approx 4.62 km from Jacksons Point

(3) Excellent 

35

Charlotte's Cottage-Lake Simcoe

Georgina / Keswick

Keswick cottage

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$138

Responds fast!
avg. 1 hour 4 minutes

Price per night from

$138

Distance approx 11.02 km from Jacksons Point

14

Lake Simcoe Lake House

Ontario / Oro Station

Oro Station house

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$301

Price per night from

$301

Distance approx 1.8 km from Jacksons Point

6

Lake Simcoe's Sutton Beauty, 4 BR, 10 Min 404, 1 Min To Lake, Year Round

Ontario / Georgina

Georgina house

4 14 1 night min

  • 4 bedrooms
  • sleeps 14
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$271

Responds fast!
avg. 2 hours 50 minutes

Price per night from

$271

Distance approx 1.44 km from Jacksons Point

13

Tuckmee Inn Bed and Breakfast- Birch Room

Georgina / Sutton

Sutton house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 2 mi
  • Air conditioning
  • Private garden

Price per night from

$82

Price per night from

$82

Distance approx 8.35 km from Jacksons Point

(1) Excellent 

19

3brm cottage with hot tub and sauna

Ontario / Innisfil

Innisfil bungalow

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 mi
  • Child Friendly

Price per night from

$147

Price per night from

$147

Distance approx 11.81 km from Jacksons Point

10

Executive family cottage

Oro Station / Shanty Bay

Shanty Bay bungalow

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$259

Responds fast!
avg. 24 minutes

Price per night from

$259

Distance approx 9.04 km from Jacksons Point

(4) Excellent 

34

Alfa Getaway ( Tuscan style)

Ontario / Innisfil

Innisfil cottage

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$82

Responds fast!
avg. 1 hour 41 minutes

Price per night from

$82

Distance approx 19.7 km from Jacksons Point

15

Private apt with deck and private yard

Ontario / Newmarket

Newmarket apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Nearest beach 20 mi
  • Child Friendly
  • Car not necessary

Price per night from

$104

Price per night from

$104

Distance approx 8.68 km from Jacksons Point

(9) Average 

25

Beautiful cottage in 50 acres of land near Lake Simcoe

Ontario / Uxbridge

Uxbridge house

6 12 3 nights min

  • 6 bedrooms
  • sleeps 12
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 24 mi
  • Child Friendly
“Great weekend” I came up with my friends for the weekend to celebrate my birthday, I was a little nervous because I didn't know what to expect because I've never done anything like this but it turned out to be a great weekend. The place is big and not
…see more

Price per night from

$258

Price per night from

$258

Distance approx 15.8 km from Jacksons Point

21

Ye Old Country Store Inn Enjoy Ski & Lake Country in Canada

Ontario / Oro Station

Oro Station chateau

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Nearest beach 5 mi
  • Child Friendly
  • Air conditioning

Price per night from

$194

Responds fast!
avg. 1 hour 56 minutes

Price per night from

$194

Distance approx 16.68 km from Jacksons Point

7

A Brand New Rental Room available in South Barrie

Ontario / Barrie

Barrie house

1 1 30 nights min

  • 1 bedroom
  • sleeps 1
  • 30 nights min
  • Air conditioning
  • Private garden

Price per night from

$26

Price per night from

$26

Distance approx 12.62 km from Jacksons Point

(1) Excellent 

14

Carriage Hills Resort Two-Bedroom Suite

Oro Station / Shanty Bay

Shanty Bay condo

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$258

Price per night from

$258

Distance approx 2.73 km from Jacksons Point

12

Cozy Cottage

Ontario / Georgina

Georgina cottage

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min

Price per night from

$123

Price per night from

$123

Distance approx 15.99 km from Jacksons Point

7

South Side Bed and Breakfast

Ontario / Barrie

Barrie b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$129

Price per night from

$129

Distance approx 13.65 km from Jacksons Point

(1) Average 

10

Furnished modern 2 bedroom executive lease

Ontario / Barrie

Barrie house

2 3 14 nights min

  • 2 bedrooms
  • sleeps 3
  • 14 nights min
  • Child Friendly

Price per night from

$68

Responds fast!
avg. 2 hours 54 minutes

Price per night from

$68

Distance approx 14.74 km from Jacksons Point

36

Modern Lake Simcoe ~ Newly built 6+ bedroom 4 bath home on Lake Simcoe

Ontario / Orillia

Orillia house

6 16 min stay varies

  • 6 bedrooms
  • sleeps 16
  • min stay varies
  • Beach / lakeside relaxation
  • Ski
  • Child Friendly

Price per night from

$562

Responds fast!
avg. 14 minutes

Price per night from

$562

Distance approx 14.08 km from Jacksons Point

5

Ravens Ridge Bed and Breakfast Sweet Dreams

Ontario / Oro-Medonte

Oro-Medonte b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min

Price per night from

$128

Price per night from

$128

Distance approx 14.17 km from Jacksons Point

(1) Average 

37

Simply Simcoe! a fabulous Carthew Bay lakefront home

Ontario / Oro Station

Oro Station house

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Beach / lakeside relaxation
  • Ski
  • Child Friendly

Price per night from

$903

Responds fast!
avg. 14 minutes

Price per night from

$903

Distance approx 8.23 km from Jacksons Point

12

Waterfront Cottage Hideaway on Lake Simcoe

Ontario / Innisfil

Innisfil house

2 7 5 nights min

  • 2 bedrooms
  • sleeps 7
  • 5 nights min
  • Child Friendly

Price per night from

$214

Price per night from

$214

Distance approx 14.08 km from Jacksons Point

7

Ravens Ridge Bed and Breakfast River Rock Suite

Ontario / Oro-Medonte

Oro-Medonte b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$111

Price per night from

$111

Distance approx 18.31 km from Jacksons Point

22

Spectacular Apartment in Newmarket, Ontario

Ontario / Newmarket

Newmarket apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$65

Price per night from

$65

Distance approx 10.38 km from Jacksons Point

(1)  

18

Lakefront home on Lake Simcoe

Ontario / Innisfil

Innisfil house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Ask about children
  • Air conditioning

Price per night from

$734

Price per night from

$734

Distance approx 19.63 km from Jacksons Point

5

Murmuring Maples

Ontario / Orillia

Orillia house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$48

Price per night from

$48

Distance approx 1.8 km from Jacksons Point

(1) Very Good 

11

Guest House by Franklin Beach

Georgina / Sutton

Sutton house

4 18 1 night min

  • 4 bedrooms
  • sleeps 18
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$429

Price per night from

$429

Distance approx 17.77 km from Jacksons Point

6

Room bachelor ensuite

Ontario / Brechin

Brechin house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$35

Responds fast!
avg. 1 hour 23 minutes

Price per night from

$35

Distance approx 4.12 km from Jacksons Point

(5) Excellent 

23

Exquisite Executive Cottage on Lake Simcoe

Georgina / Keswick

Keswick house

4 14 2 nights min

  • 4 bedrooms
  • sleeps 14
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$516

Responds fast!
avg. 1 hour 0 minutes

Price per night from

$516

Distance approx 17.74 km from Jacksons Point

9

Condo for rent

Ontario / Brechin

Brechin villa

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$112

Responds fast!
avg. 1 hour 23 minutes

Price per night from

$112

Distance approx 17.53 km from Jacksons Point

(2) Very Good 

11

Vacational rental, short or long term rental

Ontario / Brechin

Brechin villa

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$86

Responds fast!
avg. 1 hour 23 minutes

Price per night from

$86

Distance approx 14.67 km from Jacksons Point

43

Luxury Cottage On Lake Simcoe SLEEPS 16+

Ontario / Orillia

Orillia house

6 16 3 nights min

  • 6 bedrooms
  • sleeps 16
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$860

Price per night from

$860

Distance approx 14.65 km from Jacksons Point

(1) Excellent 

7

Simcoe Lake House Oasis

Ontario / Orillia

Orillia house

6 16 3 nights min

  • 6 bedrooms
  • sleeps 16
  • 3 nights min
  • Child Friendly

Price per night from

$860

Price per night from

$860

Distance approx 18.31 km from Jacksons Point

25

Fabulous Stylish 3 bedroom

Ontario / Newmarket

Newmarket house

3 7 3 nights min

  • 3 bedrooms
  • sleeps 7
  • 3 nights min
  • Child Friendly

Price per night from

$129

Price per night from

$129

Distance approx 17.58 km from Jacksons Point

9

Bradford Vacation

Ontario / Newmarket

Newmarket apartment

2 3 1 night min

  • 2 bedrooms
  • sleeps 3
  • 1 night min
  • Child Friendly

Price per night from

$78

Price per night from

$78

Distance approx 9.11 km from Jacksons Point

35

Waterfront Luxury 45min from Toronto

Ontario / Innisfil

Innisfil townhouse

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly

Price per night from

$301

Price per night from

$301