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Orangeville Vacation Rentals

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48 rentals in Orangeville.
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Furnished 3 bedroom Home with Gas Fireplace/fenced yard - Downtown Orangeville, vacation rental in Orangeville
Furnished 3 bedroom Home with Gas Fireplace/fenced yard - Downtown Orangeville, vacation rental in Orangeville
Furnished 3 bedroom Home with Gas Fireplace/fenced yard - Downtown Orangeville, vacation rental in Orangeville

Furnished 3 bedroom Home with Gas Fireplace/fenced yard - Downtown Orangeville

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Fully Furnished 2 Bedroom home . Sleeps 4. Pets $25/day/ pet max $250 per stay, vacation rental in Orangeville
Fully Furnished 2 Bedroom home . Sleeps 4. Pets $25/day/ pet max $250 per stay, vacation rental in Orangeville
Fully Furnished 2 Bedroom home . Sleeps 4. Pets $25/day/ pet max $250 per stay, vacation rental in Orangeville

Fully Furnished 2 Bedroom home . Sleeps 4. Pets $25/day/ pet max $250 per stay

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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A private & stylish urban studio, vacation rental in Orangeville
A private & stylish urban studio, vacation rental in Orangeville
A private & stylish urban studio, vacation rental in Orangeville

A private & stylish urban studio

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Hockley Hollow Hidden Treasure, vacation rental in Orangeville
Hockley Hollow Hidden Treasure, vacation rental in Orangeville
Hockley Hollow Hidden Treasure, vacation rental in Orangeville

Hockley Hollow Hidden Treasure

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Entire place, Ground level walkout Basement  with Huge backyard, vacation rental in Orangeville
Entire place, Ground level walkout Basement  with Huge backyard, vacation rental in Orangeville
Entire place, Ground level walkout Basement  with Huge backyard, vacation rental in Orangeville

Entire place, Ground level walkout Basement with Huge backyard

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Comfy 3 bedroom house with fireplace, vacation rental in Orangeville
Comfy 3 bedroom house with fireplace, vacation rental in Orangeville
Comfy 3 bedroom house with fireplace, vacation rental in Orangeville

Comfy 3 bedroom house with fireplace

Rental Home
3 bedrooms
4 bathrooms
Sleeps 3
Match: Sleeps
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Charming Rural Getaway - close to hiking and skiing, vacation rental in Orangeville
Charming Rural Getaway - close to hiking and skiing, vacation rental in Orangeville
Charming Rural Getaway - close to hiking and skiing, vacation rental in Orangeville

Charming Rural Getaway - close to hiking and skiing

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful MidCentury House on 10 Acres near Caledon, vacation rental in Orangeville
Beautiful MidCentury House on 10 Acres near Caledon, vacation rental in Orangeville
Beautiful MidCentury House on 10 Acres near Caledon, vacation rental in Orangeville

Beautiful MidCentury House on 10 Acres near Caledon

Rental Home
4 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
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Beeberry Cottage, vacation rental in Orangeville
Beeberry Cottage, vacation rental in Orangeville
Beeberry Cottage, vacation rental in Orangeville

Beeberry Cottage

Rental Home
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Up country guest house, vacation rental in Orangeville
Up country guest house, vacation rental in Orangeville
Up country guest house, vacation rental in Orangeville

Up country guest house

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Peaceful retreat  surrounded by nature in georgeous Caledon Hills, vacation rental in Orangeville
Peaceful retreat  surrounded by nature in georgeous Caledon Hills, vacation rental in Orangeville
Peaceful retreat  surrounded by nature in georgeous Caledon Hills, vacation rental in Orangeville

Peaceful retreat surrounded by nature in georgeous Caledon Hills

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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Rustic Loft in Working Horse Barn, vacation rental in Orangeville
Rustic Loft in Working Horse Barn, vacation rental in Orangeville
Rustic Loft in Working Horse Barn, vacation rental in Orangeville

Rustic Loft in Working Horse Barn

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Peartree Bed and Breakfast, vacation rental in Orangeville
Peartree Bed and Breakfast, vacation rental in Orangeville
Peartree Bed and Breakfast, vacation rental in Orangeville

Peartree Bed and Breakfast

Private Room
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Rustic Beach House With Bunkhouse | Beach Front - Located in Beautiful Ontario, vacation rental in Orangeville
Rustic Beach House With Bunkhouse | Beach Front - Located in Beautiful Ontario, vacation rental in Orangeville
Rustic Beach House With Bunkhouse | Beach Front - Located in Beautiful Ontario, vacation rental in Orangeville

Rustic Beach House With Bunkhouse | Beach Front - Located in Beautiful Ontario

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Caledon Country Estate 7 day family rental not available for weddings, vacation rental in Orangeville
Caledon Country Estate 7 day family rental not available for weddings, vacation rental in Orangeville
Caledon Country Estate 7 day family rental not available for weddings, vacation rental in Orangeville

Caledon Country Estate 7 day family rental not available for weddings

Rental Home
6 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Private and peaceful farmhouse in Hockley Valley, vacation rental in Orangeville
Private and peaceful farmhouse in Hockley Valley, vacation rental in Orangeville
Private and peaceful farmhouse in Hockley Valley, vacation rental in Orangeville

Private and peaceful farmhouse in Hockley Valley

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cottage for rent - Notre-Dame-des-Bois, vacation rental in Orangeville
Cottage for rent - Notre-Dame-des-Bois, vacation rental in Orangeville
Cottage for rent - Notre-Dame-des-Bois, vacation rental in Orangeville

Cottage for rent - Notre-Dame-des-Bois

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private Country Estate, Winter/Summer Sports, Close to Toronto, vacation rental in Orangeville
Private Country Estate, Winter/Summer Sports, Close to Toronto, vacation rental in Orangeville
Private Country Estate, Winter/Summer Sports, Close to Toronto, vacation rental in Orangeville

Private Country Estate, Winter/Summer Sports, Close to Toronto

Rental Home
4 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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Country Estate north of Brampton Ontario, vacation rental in Orangeville
Country Estate north of Brampton Ontario, vacation rental in Orangeville
Country Estate north of Brampton Ontario, vacation rental in Orangeville

Country Estate north of Brampton Ontario

Rental Home
8 bedrooms
9 bathrooms
Sleeps 12
Match: Sleeps
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Country Retreat on Horse Farm , vacation rental in Orangeville
Country Retreat on Horse Farm , vacation rental in Orangeville
Country Retreat on Horse Farm , vacation rental in Orangeville

Country Retreat on Horse Farm

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Renovated 3 bedroom house with views of lake, vacation rental in Orangeville
Renovated 3 bedroom house with views of lake, vacation rental in Orangeville
Renovated 3 bedroom house with views of lake, vacation rental in Orangeville

Renovated 3 bedroom house with views of lake

Rental Home
3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Stone Edge Estate Bed & Breakfast - Tobermory Room, vacation rental in Orangeville
Stone Edge Estate Bed & Breakfast - Tobermory Room, vacation rental in Orangeville
Stone Edge Estate Bed & Breakfast - Tobermory Room, vacation rental in Orangeville

Stone Edge Estate Bed & Breakfast - Tobermory Room

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stone Edge Estate Bed & Breakfast - Escarpment Suite (Escarpment Room and Terra, vacation rental in Orangeville
Stone Edge Estate Bed & Breakfast - Escarpment Suite (Escarpment Room and Terra, vacation rental in Orangeville
Stone Edge Estate Bed & Breakfast - Escarpment Suite (Escarpment Room and Terra, vacation rental in Orangeville

Stone Edge Estate Bed & Breakfast - Escarpment Suite (Escarpment Room and Terra

Rental Home
2 bedrooms
3 bathrooms
Sleeps 2
Match: Sleeps
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Peaceful Retreat on Horse Farm near Alliston, vacation rental in Orangeville
Peaceful Retreat on Horse Farm near Alliston, vacation rental in Orangeville
Peaceful Retreat on Horse Farm near Alliston, vacation rental in Orangeville

Peaceful Retreat on Horse Farm near Alliston

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Hockley guest cottage , vacation rental in Orangeville
Hockley guest cottage , vacation rental in Orangeville
Hockley guest cottage , vacation rental in Orangeville

Hockley guest cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Circa 1850 Settlers Cabin - Located in Tropical Ontario with Private Chef Servi, vacation rental in Orangeville
Circa 1850 Settlers Cabin - Located in Tropical Ontario with Private Chef Servi, vacation rental in Orangeville
Circa 1850 Settlers Cabin - Located in Tropical Ontario with Private Chef Servi, vacation rental in Orangeville

Circa 1850 Settlers Cabin - Located in Tropical Ontario with Private Chef Servi

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Rustic Beach House | Beach Front - Located in Wonderful Ontario, vacation rental in Orangeville
Rustic Beach House | Beach Front - Located in Wonderful Ontario, vacation rental in Orangeville
Rustic Beach House | Beach Front - Located in Wonderful Ontario, vacation rental in Orangeville

Rustic Beach House | Beach Front - Located in Wonderful Ontario

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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A setting for a rustic wedding, family reunion or wellness retreat, vacation rental in Orangeville
A setting for a rustic wedding, family reunion or wellness retreat, vacation rental in Orangeville
A setting for a rustic wedding, family reunion or wellness retreat, vacation rental in Orangeville

A setting for a rustic wedding, family reunion or wellness retreat

Rental Home
7 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Secluded Waterfront Oasis for an Amazing Getaway!, vacation rental in Orangeville
Secluded Waterfront Oasis for an Amazing Getaway!, vacation rental in Orangeville
Secluded Waterfront Oasis for an Amazing Getaway!, vacation rental in Orangeville

Secluded Waterfront Oasis for an Amazing Getaway!

Rental Home
5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Charming Bungalow 25 mins from Toronto Airport, vacation rental in Orangeville
Charming Bungalow 25 mins from Toronto Airport, vacation rental in Orangeville
Charming Bungalow 25 mins from Toronto Airport, vacation rental in Orangeville

Charming Bungalow 25 mins from Toronto Airport

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Elegant Bungalow In The Prestigious Village Of Hockley, vacation rental in Orangeville
Elegant Bungalow In The Prestigious Village Of Hockley, vacation rental in Orangeville
Elegant Bungalow In The Prestigious Village Of Hockley, vacation rental in Orangeville

Elegant Bungalow In The Prestigious Village Of Hockley

Rental Home
6 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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A spectacular cabin setting in the woods, vacation rental in Orangeville
A spectacular cabin setting in the woods, vacation rental in Orangeville
A spectacular cabin setting in the woods, vacation rental in Orangeville

A spectacular cabin setting in the woods

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Peak House - Luxury Living on this 100 acre country retreat, vacation rental in Orangeville
Peak House - Luxury Living on this 100 acre country retreat, vacation rental in Orangeville
Peak House - Luxury Living on this 100 acre country retreat, vacation rental in Orangeville

Peak House - Luxury Living on this 100 acre country retreat

Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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The Lotus Manor, vacation rental in Orangeville
The Lotus Manor, vacation rental in Orangeville
The Lotus Manor, vacation rental in Orangeville

The Lotus Manor

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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A Charming, Rustic 140-Year-Old Carriage House, vacation rental in Orangeville
A Charming, Rustic 140-Year-Old Carriage House, vacation rental in Orangeville
A Charming, Rustic 140-Year-Old Carriage House, vacation rental in Orangeville

A Charming, Rustic 140-Year-Old Carriage House

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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PARADISE OVERLOOKING THE  BUBBLING CREDIT RIVER SURRONDED BY LUSH MATURE GARDENS, vacation rental in Orangeville
PARADISE OVERLOOKING THE  BUBBLING CREDIT RIVER SURRONDED BY LUSH MATURE GARDENS, vacation rental in Orangeville
PARADISE OVERLOOKING THE  BUBBLING CREDIT RIVER SURRONDED BY LUSH MATURE GARDENS, vacation rental in Orangeville

PARADISE OVERLOOKING THE BUBBLING CREDIT RIVER SURRONDED BY LUSH MATURE GARDENS

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Entire Private Studio Apartment in Alton, Ontario, vacation rental in Orangeville
Entire Private Studio Apartment in Alton, Ontario, vacation rental in Orangeville
Entire Private Studio Apartment in Alton, Ontario, vacation rental in Orangeville

Entire Private Studio Apartment in Alton, Ontario

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful 5 Bed, 3 Bath Country House in Caledon! 2 Acres! Pool!, vacation rental in Orangeville
Beautiful 5 Bed, 3 Bath Country House in Caledon! 2 Acres! Pool!, vacation rental in Orangeville
Beautiful 5 Bed, 3 Bath Country House in Caledon! 2 Acres! Pool!, vacation rental in Orangeville

Beautiful 5 Bed, 3 Bath Country House in Caledon! 2 Acres! Pool!

Rental Home
5 bedrooms
6 bathrooms
Sleeps 13
Match: Sleeps
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Luxury estate property with heated salt water pool -sleeps 12-14!!, vacation rental in Orangeville
Luxury estate property with heated salt water pool -sleeps 12-14!!, vacation rental in Orangeville
Luxury estate property with heated salt water pool -sleeps 12-14!!, vacation rental in Orangeville

Luxury estate property with heated salt water pool -sleeps 12-14!!

Rental Home
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful 3 bedroom cottage located in Mono, vacation rental in Orangeville
Beautiful 3 bedroom cottage located in Mono, vacation rental in Orangeville
Beautiful 3 bedroom cottage located in Mono, vacation rental in Orangeville

Beautiful 3 bedroom cottage located in Mono

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Relax and Renew - your estate awaits!, vacation rental in Orangeville
Relax and Renew - your estate awaits!, vacation rental in Orangeville
Relax and Renew - your estate awaits!, vacation rental in Orangeville

Relax and Renew - your estate awaits!

Rental Home
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Comfortable and modern guest place, vacation rental in Orangeville
Comfortable and modern guest place, vacation rental in Orangeville
Comfortable and modern guest place, vacation rental in Orangeville

Comfortable and modern guest place

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Dream Country Escape with Pool and Hot Tub, vacation rental in Orangeville
Dream Country Escape with Pool and Hot Tub, vacation rental in Orangeville
Dream Country Escape with Pool and Hot Tub, vacation rental in Orangeville

Dream Country Escape with Pool and Hot Tub

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Caledon Private Living Estate! **Freshly Renovated**, vacation rental in Orangeville
Caledon Private Living Estate! **Freshly Renovated**, vacation rental in Orangeville
Caledon Private Living Estate! **Freshly Renovated**, vacation rental in Orangeville

Caledon Private Living Estate! **Freshly Renovated**

Rental Home
3 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Charming Log Home - 25 private acres in Caledon, vacation rental in Orangeville
Charming Log Home - 25 private acres in Caledon, vacation rental in Orangeville
Charming Log Home - 25 private acres in Caledon, vacation rental in Orangeville

Charming Log Home - 25 private acres in Caledon

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Beautiful Cottage in Caledon East, vacation rental in Orangeville
Beautiful Cottage in Caledon East, vacation rental in Orangeville
Beautiful Cottage in Caledon East, vacation rental in Orangeville

Beautiful Cottage in Caledon East

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Little Happy Place, vacation rental in Orangeville
Little Happy Place, vacation rental in Orangeville
Little Happy Place, vacation rental in Orangeville

Little Happy Place

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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SLEEP UNDER THE STARS - INDOORS, vacation rental in Orangeville
SLEEP UNDER THE STARS - INDOORS, vacation rental in Orangeville
SLEEP UNDER THE STARS - INDOORS, vacation rental in Orangeville

SLEEP UNDER THE STARS - INDOORS

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stone Edge Estate Bed & Breakfast - Queenston Room, vacation rental in Orangeville
Stone Edge Estate Bed & Breakfast - Queenston Room, vacation rental in Orangeville
Stone Edge Estate Bed & Breakfast - Queenston Room, vacation rental in Orangeville

Stone Edge Estate Bed & Breakfast - Queenston Room

Rental Home
1 bedroom
2 bathrooms
Sleeps 1
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