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86 Houses

(8) Very Good 

57

Million Dollar Lake Views Every Level 10+ Location

Muskoka Lakes / Windermere

Windermere cottage

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Nearest beach 6 mi
  • Child Friendly
  • Air conditioning

Price per night from

$454

Price per night from

$454

(8) Excellent 

19

The Roost Cottage, Windermere, Muskoka, Ontario

Muskoka Lakes / Windermere

Windermere guest house

2 4 3 nights min

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

Price per night from

$215

Price per night from

$215

Great rentals within 20 miles that match your search

Distance approx 15.45 km from Windermere

8

Beautiful Two Bedroom Cottage on Kapikog Lake

Muskoka District / Mactier

Mactier cottage

2 4 7 nights min

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

Price per night from

$159

Price per night from

$159

Distance approx 3.78 km from Windermere

48

Muskoka Reflections ~ family fun minutes from Port Carling

Muskoka Lakes / Port Carling

Port Carling cottage

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$885

Responds fast!
avg. 14 minutes

Price per night from

$885

Distance approx 4.94 km from Windermere

35

Muskoka Birch On Lake Rosseau

Muskoka Lakes / Minett

Minett cottage

5 8 7 nights min

  • 5 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.01 mi
  • Child Friendly

Price per night from

$344

Price per night from

$344

Distance approx 14.11 km from Windermere

27

Dining Room Cottage - Clyffe House Cottage Resort

Huntsville / Port Sydney

Port Sydney cottage

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Child Friendly

Price per night from

$299

Price per night from

$299

Distance approx 13.18 km from Windermere

(1) Excellent 

16

Lake Muskoka Getaway

Muskoka District / Bracebridge

Bracebridge cottage

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$400

Price per night from

$400

Distance approx 9.6 km from Windermere

36

Cottage in the Muskokas

Muskoka District / Bracebridge

Bracebridge cottage

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$166

Price per night from

$166

Distance approx 5.83 km from Windermere

67

Wildwood Cottage Lake Joseph

Muskoka Lakes / Port Carling

Port Carling cottage

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$1,151

Responds fast!
avg. 14 minutes

Price per night from

$1,151

Distance approx 19.27 km from Windermere

(1) Excellent 

28

Muskoka Rustic Beauty - Cottage Six Mile Lake

Muskoka District / Port Severn

Port Severn cottage

3 6 min stay varies

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

Price per night from

$280

Price per night from

$280

Distance approx 8.2 km from Windermere

(1) Very Good 

18

Muskoka, bass lake

Muskoka District / Mactier

Mactier cottage

7 15 7 nights min

  • 7 bedrooms
  • sleeps 15
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$344

Responds fast!
avg. 3 hours 31 minutes

Price per night from

$344

Distance approx 19.53 km from Windermere

(4) Excellent 

32

'Mellow Yellow' - 5 Bedroom Luxury Muskoka Cottage

Muskoka District / Gravenhurst

Gravenhurst cottage

5 12 3 nights min

  • 5 bedrooms
  • sleeps 12
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Ask about pets

Price per night from

$459

Responds fast!
avg. 3 hours 49 minutes

Price per night from

$459

Distance approx 14.05 km from Windermere

(3) Very Good 

29

The Main Lodge Cottage - Clyffe House Cottage Resort

Huntsville / Port Sydney

Port Sydney cottage

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly

Price per night from

$214

Price per night from

$214

Distance approx 19.37 km from Windermere

19

Private 4 Bedroom Muskoka Cottage

Muskoka District / Gravenhurst

Gravenhurst cottage

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Ask about pets

Price per night from

$260

Price per night from

$260

Distance approx 18.04 km from Windermere

(2) Excellent 

36

Lake Muskoka Cottage Rental

Muskoka District / Muskoka Lakes

Muskoka Lakes cottage

5 11 7 nights min

  • 5 bedrooms
  • sleeps 11
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$593

Price per night from

$593

Distance approx 8.2 km from Windermere

13

Muskoka, bass lake Cottage No. 2

Muskoka District / Muskoka Lakes

Muskoka Lakes house

4 2 7 nights min

  • 4 bedrooms
  • sleeps 2
  • 7 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$221

Responds fast!
avg. 3 hours 31 minutes

Price per night from

$221

Distance approx 18.44 km from Windermere

17

BedRock Mansion Retreat

Muskoka District / Gravenhurst

Gravenhurst villa

4 12 6 nights min

  • 4 bedrooms
  • sleeps 12
  • 6 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$597

Price per night from

$597

Distance approx 19.53 km from Windermere

(3) Excellent 

25

Awesome Buck Lake Cottage - ATV-Sled-Relax-FUN!

Muskoka District / Huntsville

Huntsville cottage

4 10 1 night min

  • 4 bedrooms
  • sleeps 10
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 mi
  • Child Friendly

Price per night from

$258

Responds fast!
avg. 3 hours 14 minutes

Price per night from

$258

Distance approx 15.31 km from Windermere

6

Room with covered Porch and Cable by Falls in town

Muskoka District / Bracebridge

Bracebridge house

1 1 1 night min

  • 1 bedroom
  • sleeps 1
  • 1 night min

Price per night from

$52

Responds fast!
avg. 7 minutes

Price per night from

$52

Distance approx 13.78 km from Windermere

67

The Family that Boathouses together, stays together...

Huntsville / Port Sydney

Port Sydney cottage

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$341

Responds fast!
avg. 14 minutes

Price per night from

$341

Distance approx 17.21 km from Windermere

(3) Excellent 

23

Luxury Waterfront Cottage, Fox Lake in Huntsville

Muskoka District / Huntsville

Huntsville cottage

3 9 2 nights min

  • 3 bedrooms
  • sleeps 9
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$344

Price per night from

$344

Distance approx 17.53 km from Windermere

44

Lakefront Treasure

Ontario / Kawartha Lakes

Kawartha Lakes cottage

3 8 7 nights min

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

Price per night from

$344

Price per night from

$344

Distance approx 10.68 km from Windermere

89

Kilty Cottage - perfect for families!

Muskoka Lakes / Minett

Minett house

5 14 min stay varies

  • 5 bedrooms
  • sleeps 14
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$587

Responds fast!
avg. 14 minutes

Price per night from

$587

Distance approx 17.38 km from Windermere

(3) Excellent 

6

Even Kiehl Bed & Breakfast

Muskoka District / Gravenhurst

Gravenhurst b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 2 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$121

Responds fast!
avg. 3 hours 42 minutes

Price per night from

$121

Distance approx 8.62 km from Windermere

15

Lake Joseph Muskoka Cottage Rental

Muskoka District / Mactier

Mactier cottage

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$860

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$860

Distance approx 14.18 km from Windermere

24

Dance Hall (Lower) - Clyffe House Cottage Resort

Huntsville / Port Sydney

Port Sydney cottage

3 6 7 nights min

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

Price per night from

$189

Price per night from

$189

Distance approx 16.76 km from Windermere

(1) Very Good 

25

Cottage in Muskoka-Lake Vernon Huntsville

Muskoka District / Huntsville

Huntsville cottage

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$258

Price per night from

$258

Distance approx 3.66 km from Windermere Show on Map

53

4 bed 3 bath family cottage

Muskoka Lakes / Port Carling

Port Carling cottage

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$723

Responds fast!
avg. 14 minutes

Price per night from

$723

Distance approx 19.28 km from Windermere

12

Cottage Rental on Beautiful Six Mile Lake

Muskoka District / Big Chute

Big Chute cottage

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly

Price per night from

$246

Price per night from

$246

Distance approx 12.08 km from Windermere

35

Lake Muskoka Family Compound set on a private peninsula!

Muskoka District / Gravenhurst

Gravenhurst cottage

4 10 70 nights min

  • 4 bedrooms
  • sleeps 10
  • 70 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$993

Responds fast!
avg. 14 minutes

Price per night from

$993

Distance approx 8.6 km from Windermere

24

Lake Muskoka 4 BR Cottage, Sandy Beach, Sunny Decks, Private

Muskoka District / Muskoka Lakes

Muskoka Lakes cottage

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$361

Price per night from

$361

Distance approx 9.91 km from Windermere

50

Gorgeous recently built cottage & boathouse on Acton Island with south views ove

Muskoka Lakes / Bala

Bala house

7 12 min stay varies

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

Price per night from

$1,613

Responds fast!
avg. 14 minutes

Price per night from

$1,613

Distance approx 12.19 km from Windermere

26

Lake Joseph Family Compound

Northeastern Ontario / Seguin

Seguin house

7 13 7 nights min

  • 7 bedrooms
  • sleeps 13
  • 7 nights min
  • Child Friendly

Price per night from

$1,223

Responds fast!
avg. 14 minutes

Price per night from

$1,223

Distance approx 17.94 km from Windermere

15

Muskoka Luxury Cottage-Private- Beachfront- Dock & Toys

Muskoka District / Gravenhurst

Gravenhurst cottage

4 8 3 nights min

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

Price per night from

$430

Price per night from

$430

Distance approx 17.87 km from Windermere

52

Luxurious Lakefront Splendour on Horseshoe Lake

Northeastern Ontario / Parry Sound

Parry Sound house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$1,083

Responds fast!
avg. 14 minutes

Price per night from

$1,083

Distance approx 6.28 km from Windermere

(8) Excellent 

22

The Hermitage

Muskoka District / Muskoka Lakes

Muskoka Lakes cottage

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$541

Responds fast!
avg. 3 hours 17 minutes

Price per night from

$541

Distance approx 15.31 km from Windermere

17

Luxury Glamping and All Terrain Vehicle Rentals (ATVs, UTVs and snowmobiles)

Muskoka District / Bracebridge

Bracebridge tented camp

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

Price per night from

$335

Price per night from

$335

Distance approx 18.33 km from Windermere

16

Go Home Lake Beautiful Roadaccess Cottage

Muskoka District / Mactier

Mactier cottage

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly

Price per night from

$344

Price per night from

$344