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47 Houses

9

Cottage with hot tub and sauna

Innisfil / Cookstown

Cookstown house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly

Price per night from

$147

Price per night from

$147

(2) Excellent 

13

Cedar Stone Cottage/Vacation Rental

Innisfil / Cookstown

Cookstown house

3 6 2 nights min

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

Price per night from

$216

Responds fast!
avg. 2 hours 18 minutes

Price per night from

$216

Great rentals within 20 miles that match your search

Distance approx 19.84 km from Cookstown

8

All Season Retreat on Lake Simcoe

Ontario / Oro Station

Oro Station cottage

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Ask about children
  • Pet Friendly

Price per night from

$172

Price per night from

$172

Distance approx 14.38 km from Cookstown Show on Map

(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 16.99 km from Cookstown Show on Map

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

$272

Responds fast!
avg. 2 hours 43 minutes

Price per night from

$272

Distance approx 14.32 km from Cookstown Show on Map

(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 11.72 km from Cookstown Show on Map

(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 16.12 km from Cookstown

9

Jecara Farms - Bear Cabin

Ontario / Schomberg

Schomberg cottage

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly

Price per night from

$173

Responds fast!
avg. 1 hour 39 minutes

Price per night from

$173

Distance approx 12.01 km from Cookstown Show on Map

10

3 Bedroom Furnished Apartment

Ontario / Barrie

Barrie apartment

3 5 14 nights min

  • 3 bedrooms
  • sleeps 5
  • 14 nights min
  • Child Friendly
  • Car not necessary

Price per night from

$77

Responds fast!
avg. 2 hours 54 minutes

Price per night from

$77

Distance approx 10.88 km from Cookstown

(5) Excellent 

Certificate of Excellence

26

Country Cabin on Farm Near Newmarket Toronto

Ontario / Schomberg

Schomberg guest house

1 6 1 night min

  • 1 bedroom
  • sleeps 6
  • 1 night min
  • Nearest beach 44 mi
  • Child Friendly
  • Air conditioning

Certificate of Excellence

Price per night from

$100

Price per night from

$100

Distance approx 16.12 km from Cookstown

5

Jecara Farms - Snake Cabin

Ontario / Schomberg

Schomberg cottage

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly

Price per night from

$130

Responds fast!
avg. 1 hour 39 minutes

Price per night from

$130

Distance approx 11.29 km from Cookstown Show on Map

(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 45 minutes

Price per night from

$82

Distance approx 16.32 km from Cookstown

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 16.09 km from Cookstown

(1) Excellent 

6

Jecara Farms - Raven Cabin

Ontario / Schomberg

Schomberg cottage

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly

Price per night from

$129

Responds fast!
avg. 2 hours 28 minutes

Price per night from

$129

Distance approx 15.47 km from Cookstown

(4) Very Good 

23

NEWMARKET - 30 minutes north of Toronto near Ontario's vacationland!

Ontario / Newmarket

Newmarket house

1 9 7 nights min

  • 1 bedroom
  • sleeps 9
  • 7 nights min
  • Nearest beach 30 mi
  • Swimming pool
  • Air conditioning

Price per night from

$173

Responds fast!
avg. 1 hour 21 minutes

Price per night from

$173

Distance approx 11.22 km from Cookstown Show on Map

11

SHABBY SHACK

Ontario / Innisfil

Innisfil beach hut

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

Price per night from

$57

Responds fast!
avg. 1 hour 41 minutes

Price per night from

$57

Distance approx 14.32 km from Cookstown

(1) Very Good 

13

Relaxing Nature Retreat, Everett, Ontario - 1 Free Night (email for details)

Ontario / Mansfield

Mansfield lodge

5 10 1 night min

  • 5 bedrooms
  • sleeps 10
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$78

Responds fast!
avg. 3 hours 54 minutes

Price per night from

$78

Distance approx 11.01 km from Cookstown Show on Map

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 18.79 km from Cookstown

(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

Distance approx 17.22 km from Cookstown Show on Map

24

Stunning Big Bay Point Lake House

Ontario / Innisfil

Innisfil house

4 8 4 nights min

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

Price per night from

$518

Responds fast!
avg. 2 hours 33 minutes

Price per night from

$518

Distance approx 15.97 km from Cookstown Show on Map

12

Cozy Cottage

Ontario / Georgina

Georgina cottage

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min

Price per night from

$124

Price per night from

$124

Distance approx 12.37 km from Cookstown Show on Map

(2) Excellent 

17

Barrie. Very very private 4 acres, Whole Property

Ontario / Barrie

Barrie house

4 16 2 nights min

  • 4 bedrooms
  • sleeps 16
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$346

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$346

Distance approx 10.87 km from Cookstown

9

Camp Site in the GTA w/ Optional Tent / Gear - 2

Ontario / Schomberg

Schomberg tented camp

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Nearest beach 44 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$35

Price per night from

$35

Distance approx 16.34 km from Cookstown Show on Map

(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 10.88 km from Cookstown

7

Holiday Christmas Event Hosting Space in Country

Ontario / Schomberg

Schomberg house

1 40 1 night min

  • 1 bedroom
  • sleeps 40
  • 1 night min
  • Child Friendly

Price per night from

$259

Price per night from

$259

Distance approx 12.15 km from Cookstown Show on Map

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 12.01 km from Cookstown Show on Map

(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

$69

Responds fast!
avg. 2 hours 54 minutes

Price per night from

$69

Distance approx 14.8 km from Cookstown Show on Map

46

Luxury Accommodation At A Reasonable Price

Ontario / Barrie

Barrie b and b

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$259

Price per night from

$259

Distance approx 14.32 km from Cookstown

19

Spiritual/Religious/Nature Retreat

Adjala–Tosorontio / Everett

Everett lodge

8 20 1 night min

  • 8 bedrooms
  • sleeps 20
  • 1 night min
  • Child Friendly
  • Pet Friendly

Price per night from

$39

Price per night from

$39

Distance approx 13.26 km from Cookstown Show on Map

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 11.62 km from Cookstown Show on Map

(1) Excellent 

16

Georgina Lakeshore Vacation Home

Georgina / Keswick

Keswick house

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$198

Responds fast!
avg. 2 hours 29 minutes

Price per night from

$198

Distance approx 16.16 km from Cookstown

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 17 km from Cookstown Show on Map

(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

$431

Price per night from

$431

Distance approx 8.77 km from Cookstown Show on Map

(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

$737

Price per night from

$737

Distance approx 14.86 km from Cookstown Show on Map

(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

$518

Responds fast!
avg. 1 hour 0 minutes

Price per night from

$518

Distance approx 12.94 km from Cookstown

4

Luxury 3 Bedrooms in Westin Dawn Beach Club

Ontario / Toronto

Toronto apartment

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$606

Price per night from

$606

Distance approx 16.29 km from Cookstown Show on Map

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

$302

Price per night from

$302

Distance approx 8.7 km from Cookstown Show on Map

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