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Search results; Over 1,000 homes in Caledon

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Superhost
Boutique hotel in Caledon
Cheltenham Suites - The Badlands Suite
2 bedrooms, 2 beds, 1 shared bathroom
27 Sept – 2 Oct
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4.8 out of 5 average rating, 76 reviews
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Guest favourite
Home in Caledon
Modern- Cozy House by Nature for Full Family of 13
5 bedrooms, 7 beds, 4.5 bathrooms
14–19 Sept
4.91 out of 5 average rating, 22 reviews
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Home in Caledon
Charming Home Near Caledon Trails
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
New place to stay
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Superhost
Home in Caledon
Modern Family Home•Fireplace•Backyard•NearBrampton
3 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 85 reviews
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Home in Caledon
A comfortable peaceful home!
3 bedrooms, 3 queen beds, 3.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Orangeville
Elba Haus | 63-Acre Private Retreat + Hot Tub
5 bedrooms, 5 beds, 4 bathrooms
8–13 Sept
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Cabin in Mansfield
High Crest Hideaway
2 bedrooms, 2 queen beds, 2 bathrooms
25–30 Oct
4.89 out of 5 average rating, 141 reviews
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Guest favourite
Home in Caledon
Modern 2BR Private Suite | Prime Location
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Caledon
Luxury - Sleeps 10 - Smart Home - PS5 - 85” OLED
4 bedrooms, 6 beds, 3.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 13 reviews
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Home in Brampton
Private Estate | Hot Tub & Pickleball
5 bedrooms, 5 king beds, 3 bathrooms
1–6 Sept
New place to stay
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Top guest favourite
Guest suite in Orangeville
Garden Studio Orangeville
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
5.0 out of 5 average rating, 202 reviews
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Guest favourite
Home in Bolton West
A Private Oasis with Fireplace
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 13 reviews
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Flat in Alton
Serene historic village retreat.
1 bedroom, 1 bed, 1 bathroom
1–6 Sept
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Guest favourite
Flat in Alton
The Potters Retreat
2 bedrooms, 2 king beds, 1.5 bathrooms
19–24 Oct
4.97 out of 5 average rating, 37 reviews
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Top guest favourite
Flat in Bolton West
Newly built Bolton Studio
2 beds, 1 bathroom
2–7 Nov
4.92 out of 5 average rating, 59 reviews
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Guest favourite
Guest suite in Bolton West
Guests praise:Spotlessly Clean, SelfCheck-In, WiFi
2 bedrooms, 2 queen beds, 1.5 bathrooms
2–7 Sept
4.99 out of 5 average rating, 90 reviews
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Top guest favourite
Home in Bolton West
Bright 3-Bedroom Main Floor Suite in Bolton West
3 bedrooms, 3 beds, 1 bathroom
21–26 Oct
5.0 out of 5 average rating, 25 reviews
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Guest house in Orangeville
Hideaway newly built
1 bedroom, 4 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 7 reviews
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Home in Alton
Close to TPC Toronto, Alton Mill & Millcroft Inn
4 bedrooms, 4 beds, 3.5 bathrooms
1–6 Jul
5.0 out of 5 average rating, 9 reviews