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Windermere Holiday Rentals

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50 rentals in Windermere.
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Beautiful Custom Built Muskoka Boathouse!, holiday rental in Windermere

Beautiful Custom Built Muskoka Boathouse!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Muskoka Family Cottage On Crystal Clear High Lake, holiday rental in Windermere

Muskoka Family Cottage On Crystal Clear High Lake

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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MUSKOKA HISTORIC LOG GUEST CABIN ON SKELETON LAKE, holiday rental in Windermere

MUSKOKA HISTORIC LOG GUEST CABIN ON SKELETON LAKE

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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MUSKOKA'S BEST KEPT SECRET - SKELETON LAKE, holiday rental in Windermere

MUSKOKA'S BEST KEPT SECRET - SKELETON LAKE

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Roost Cottage, Windermere, Muskoka, Ontario, holiday rental in Windermere

The Roost Cottage, Windermere, Muskoka, Ontario

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Executive Boathouse, holiday rental in Windermere

Executive Boathouse

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful. comfortable cottage, amazing Lake views. Family friendly. Huge deck., holiday rental in Windermere

Beautiful. comfortable cottage, amazing Lake views. Family friendly. Huge deck.

3 bedrooms
1 bathroom
Sleeps 9
Match: Sleeps
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Barefoot BEACH  living in Muskoka, holiday rental in Windermere

Barefoot BEACH living in Muskoka

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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TuckAway Rustic Lakefront Cottage in Muskoka, holiday rental in Windermere

TuckAway Rustic Lakefront Cottage in Muskoka

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Historic Lake Rosseau - Family Friendly, holiday rental in Windermere

Historic Lake Rosseau - Family Friendly

6 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Cozy Four Season Cottage on Brandy Lake, holiday rental in Windermere

Cozy Four Season Cottage on Brandy Lake

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lake Joseph Luxury Retreat, holiday rental in Windermere

Lake Joseph Luxury Retreat

6 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Spacious Family Friendly Cottage On Lake Mckechnie!, holiday rental in Windermere

Spacious Family Friendly Cottage On Lake Mckechnie!

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Welcome to Serendipity on Lake Muskoka! Gorgeous Island Dotted View!, holiday rental in Windermere

Welcome to Serendipity on Lake Muskoka! Gorgeous Island Dotted View!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lovely Quaint Cottage In A Quiet Bay On Lake  Rosseau, Muskoka, holiday rental in Windermere

Lovely Quaint Cottage In A Quiet Bay On Lake Rosseau, Muskoka

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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The 'Yellow Cottage' - A modern rustic Muskoka Cottage on 300' shoreline, holiday rental in Windermere

The 'Yellow Cottage' - A modern rustic Muskoka Cottage on 300' shoreline

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Lake Muskoka Cottage Compound, holiday rental in Windermere

Beautiful Lake Muskoka Cottage Compound

7 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Bala-Retreat on Moon River in Muskoka, holiday rental in Windermere

Bala-Retreat on Moon River in Muskoka

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sunset Cove Muskoka Lake, holiday rental in Windermere

Sunset Cove Muskoka Lake

4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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'SERENITY IN MUSKOKA' Beautiful Waterfront Cottage, holiday rental in Windermere

'SERENITY IN MUSKOKA' Beautiful Waterfront Cottage

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Great Location and Fun For Everyone!, holiday rental in Windermere

Great Location and Fun For Everyone!

3 bedrooms
1 bathroom
Sleeps 9
Match: Sleeps
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Moon River Ridge Lodge, holiday rental in Windermere

Moon River Ridge Lodge

4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Lake Joseph, Muskoka - 7 Bedroom Family Cottage - Quiet Bay. Gorgeous setting., holiday rental in Windermere

Lake Joseph, Muskoka - 7 Bedroom Family Cottage - Quiet Bay. Gorgeous setting.

8 bedrooms
3 bathrooms
Sleeps 20
Match: Sleeps
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Muskoka Riverside Log Home, holiday rental in Windermere

Muskoka Riverside Log Home

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Celebrate Everything - A Muskoka Beauty | 1,800sqf plus bunkie & dry boathouse, holiday rental in Windermere

Celebrate Everything - A Muskoka Beauty | 1,800sqf plus bunkie & dry boathouse

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Last week in August still available!, holiday rental in Windermere

Last week in August still available!

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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MUSKOKAN CLUB RESORT -  YEAR-ROUND LUXURY, holiday rental in Windermere

MUSKOKAN CLUB RESORT - YEAR-ROUND LUXURY

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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WHITE BIRCHES CAMP, holiday rental in Windermere

WHITE BIRCHES CAMP

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sunset Views On Lake Muskoka, holiday rental in Windermere

Sunset Views On Lake Muskoka

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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The Main Lodge Cottage - Clyffe House Cottage Resort, holiday rental in Windermere

The Main Lodge Cottage - Clyffe House Cottage Resort

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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A Private Family Compound On 1.5 Beautiful Acres With 215 Feet Of Waterfront, holiday rental in Windermere

A Private Family Compound On 1.5 Beautiful Acres With 215 Feet Of Waterfront

8 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Cottage in the Muskokas, holiday rental in Windermere

Cottage in the Muskokas

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Perfect Getaway in the heart of Muskoka, holiday rental in Windermere

Perfect Getaway in the heart of Muskoka

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Dream Cottage in Muskoka, holiday rental in Windermere

Dream Cottage in Muskoka

9 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
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Lake Joseph Muskoka Cottage Rental, holiday rental in Windermere

Lake Joseph Muskoka Cottage Rental

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Bass Lake Retreat, holiday rental in Windermere

Bass Lake Retreat

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Muskoka Lake Boathouse/Cottage Port Carling/Bala: Most of Fall Open!, holiday rental in Windermere

Beautiful Muskoka Lake Boathouse/Cottage Port Carling/Bala: Most of Fall Open!

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Family Friendly Waterfront Property on Lake Joseph, Muskoka, holiday rental in Windermere

Family Friendly Waterfront Property on Lake Joseph, Muskoka

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Million Dollar Lake Rosseau Lake Views, holiday rental in Windermere

Million Dollar Lake Rosseau Lake Views

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Renovated, rustic, lake view Muskoka cottage on Bass Lake  with chef’s kitchen., holiday rental in Windermere

Renovated, rustic, lake view Muskoka cottage on Bass Lake with chef’s kitchen.

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A Cozy House in the Woods, holiday rental in Windermere

A Cozy House in the Woods

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Red Oaks Muskoka Waterfront Cottage, holiday rental in Windermere

The Red Oaks Muskoka Waterfront Cottage

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Freshly Renovated, Modernized, Water's Edge Cottage., holiday rental in Windermere

Freshly Renovated, Modernized, Water's Edge Cottage.

4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Wares Muskoka Lakes Estate (with sauna), holiday rental in Windermere

Wares Muskoka Lakes Estate (with sauna)

6 bedrooms
3 bathrooms
Sleeps 17
Match: Sleeps
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Bala Island Getaway on Lake Muskoka, holiday rental in Windermere

Bala Island Getaway on Lake Muskoka

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Cottage on Lake Muskoka with Hot Tub, holiday rental in Windermere

Beautiful Cottage on Lake Muskoka with Hot Tub

5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Spacious Muskoka Cottage on Lake Joseph w Boathouse, holiday rental in Windermere

Spacious Muskoka Cottage on Lake Joseph w Boathouse

5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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The Hideaway Cottage - Bala, Ontario - Muskoka, holiday rental in Windermere

The Hideaway Cottage - Bala, Ontario - Muskoka

4 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Muskoka - Lake Rousseau Hotel Atpartment

0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
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Cozy Waterfront Lake Muskoka Property, holiday rental in Windermere

Cozy Waterfront Lake Muskoka Property

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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