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Holiday Homes in Orillia

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50 rentals in Orillia.
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Amazing fully upgraded 3 bedroom+ new furniture, 1 full bath lake property, holiday rental in Orillia

Amazing fully upgraded 3 bedroom+ new furniture, 1 full bath lake property

3 bedrooms
1 bathroom
Sleeps 8
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Family and Friend Gateway to Sunshine city

0 bedrooms
0 bathrooms
Sleeps 0
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Leaning Tree Cottage, holiday rental in Orillia

Leaning Tree Cottage

3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Beautiful Waterfront Cottage - Boater's Paradise, holiday rental in Orillia

Beautiful Waterfront Cottage - Boater's Paradise

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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EXECUTIVE WATERFRONT ON BASS LAKE ORILLIA -SUMMER!, holiday rental in Orillia

EXECUTIVE WATERFRONT ON BASS LAKE ORILLIA -SUMMER!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Family Cottage Escape on Lake Couchiching, holiday rental in Orillia

Family Cottage Escape on Lake Couchiching

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cute and relaxing cottage on the lake, holiday rental in Orillia

Cute and relaxing cottage on the lake

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lake Simcoe Waterfront Cottage Getaway, holiday rental in Orillia

Lake Simcoe Waterfront Cottage Getaway

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Luxury Chalet Cottage Simcoe, holiday rental in Orillia

Luxury Chalet Cottage Simcoe

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Peaceful Waterfront Retreat on Lake Simcoe, holiday rental in Orillia

Peaceful Waterfront Retreat on Lake Simcoe

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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HOT TUB-Natural paradise, timber frame, sauna, close to Casino and ski hill., holiday rental in Orillia

HOT TUB-Natural paradise, timber frame, sauna, close to Casino and ski hill.

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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COZY COTTAGE WALKING DISTANCE TO LAKE SIMCOE & FRIDAY HARBOUR, holiday rental in Orillia

COZY COTTAGE WALKING DISTANCE TO LAKE SIMCOE & FRIDAY HARBOUR

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lake Simcoe Cottage across Thorah Centennial Park, Beaverton Ontario ice fishing, holiday rental in Orillia

Lake Simcoe Cottage across Thorah Centennial Park, Beaverton Ontario ice fishing

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Friday Harbour - Ontario All Season Luxury Resort, holiday rental in Orillia

Friday Harbour - Ontario All Season Luxury Resort

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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All year around newly renovated cul de sec quiet cottage with new hot tub, holiday rental in Orillia

All year around newly renovated cul de sec quiet cottage with new hot tub

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Horseshoe Valley Fieldview Farm, holiday rental in Orillia

Horseshoe Valley Fieldview Farm

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Luxurious Lake front Island Twnhome Friday Harbour, holiday rental in Orillia

Luxurious Lake front Island Twnhome Friday Harbour

4 bedrooms
5 bathrooms
Sleeps 16
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Horseshoe Valley Farm, holiday rental in Orillia

Horseshoe Valley Farm

3 bedrooms
2 bathrooms
Sleeps 7
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Wifi! Brand New Waterfront Contemporary Rebuild; High-End Finishes and Amenities, holiday rental in Orillia

Wifi! Brand New Waterfront Contemporary Rebuild; High-End Finishes and Amenities

6 bedrooms
3 bathrooms
Sleeps 12
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Country Charm - 2, holiday rental in Orillia

Country Charm - 2

3 bedrooms
1 bathroom
Sleeps 3
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Shamrock Bay Resort Cottage, holiday rental in Orillia

Shamrock Bay Resort Cottage

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Myrna's Chateau in beautiful Lagoon City, holiday rental in Orillia

Myrna's Chateau in beautiful Lagoon City

4 bedrooms
4 bathrooms
Sleeps 8
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Dream Cottage on the lake, holiday rental in Orillia

Dream Cottage on the lake

5 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Friday Harbour Resort on Lake Simcoe, holiday rental in Orillia

Friday Harbour Resort on Lake Simcoe

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy lake front cottage, holiday rental in Orillia

Cozy lake front cottage

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Ye Old Country Store Inn Enjoy Ski & Lake Country in Canada, holiday rental in Orillia

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

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Luxury 2 BR condo in Friday Harbour Resort - Lake Simcoe, holiday rental in Orillia

Luxury 2 BR condo in Friday Harbour Resort - Lake Simcoe

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Guest House meets Cottage on private 9 acres - fully equipped / self contained, holiday rental in Orillia

Guest House meets Cottage on private 9 acres - fully equipped / self contained

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Clean Picturesque Boater Paradise, holiday rental in Orillia

Clean Picturesque Boater Paradise

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Cozy Chalet in Horseshoe Valley, holiday rental in Orillia

Cozy Chalet in Horseshoe Valley

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Carriage Hills Resort Two-Bedroom Suite, holiday rental in Orillia

Carriage Hills Resort Two-Bedroom Suite

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Carriage Hills Resort Fabulous 2 br sleep8, holiday rental in Orillia

Carriage Hills Resort Fabulous 2 br sleep8

2 bedrooms
2 bathrooms
Sleeps 8
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Ravens Ridge Bed and Breakfast Rose Garden, holiday rental in Orillia

Ravens Ridge Bed and Breakfast Rose Garden

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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ENJOY ENTIRE WATERFRONT COTTAGE EXPERIENCE!, holiday rental in Orillia

ENJOY ENTIRE WATERFRONT COTTAGE EXPERIENCE!

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Cozy Waterfront Cottage, holiday rental in Orillia

Cozy Waterfront Cottage

4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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All Season Retreat on Lake Simcoe, holiday rental in Orillia

All Season Retreat on Lake Simcoe

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Stunning Big Bay Point Lake House, holiday rental in Orillia

Stunning Big Bay Point Lake House

4 bedrooms
3 bathrooms
Sleeps 8
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Walk Out & Ski!!, holiday rental in Orillia

Walk Out & Ski!!

2 bedrooms
2 bathrooms
Sleeps 6
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Carriage Ridge Resort 2 bedroom suite, holiday rental in Orillia

Carriage Ridge Resort 2 bedroom suite

2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Country Charm -1, holiday rental in Orillia

Country Charm -1

2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Country Charm - 3, holiday rental in Orillia

Country Charm - 3

4 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Country Charm - 4, holiday rental in Orillia

Country Charm - 4

4 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Sm Cabin for 2- shared washroom, holiday rental in Orillia

Sm Cabin for 2- shared washroom

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Alquilo semana del 24 al 31 Agosto en Espectacular Resort Ontario Canada, holiday rental in Orillia

Rent week from 24 to 31 August at Spectacular Resort Ontario Canada

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Ravens Ridge Bed and Breakfast Sweet Dreams, holiday rental in Orillia

Ravens Ridge Bed and Breakfast Sweet Dreams

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Ravens Ridge Bed and Breakfast River Rock Suite, holiday rental in Orillia

Ravens Ridge Bed and Breakfast River Rock Suite

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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2BR 2 Bath Brand New Luxury Condo - Perfect Vacation rental, holiday rental in Orillia

2BR 2 Bath Brand New Luxury Condo - Perfect Vacation rental

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lake house on Simcoe, holiday rental in Orillia

Lake house on Simcoe

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Lakefront Cottage Near Barrie, holiday rental in Orillia

Lakefront Cottage Near Barrie

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Lagoon City luxurious waterfront Villa - over 5000 SqFt, holiday rental in Orillia

Lagoon City luxurious waterfront Villa - over 5000 SqFt

5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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