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Search results; Over 1,000 homes in Caledon

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Superhost
Home in Caledon
8 Acre Retreat | 5 min to TPC Osprey + Hot Tub!
2 bedrooms, 2 beds, 2.5 private bathrooms
4–9 Oct
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4.72 out of 5 average rating, 50 reviews
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Guest favourite
Home in Caledon
100% privacy 7 bed 6 bath with 7 beds Brand new
7 bedrooms, 7 beds
25–30 Oct
4.96 out of 5 average rating, 26 reviews
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Top guest favourite
Home in Caledon
Modern Family Home•Fireplace•Backyard•NearBrampton
3 bedrooms, 3 beds
11–16 Oct
4.94 out of 5 average rating, 93 reviews
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Guest favourite
Home in Caledon
Modern- Cozy House by Nature for Full Family of 13
5 bedrooms, 7 beds
1–6 Oct
4.91 out of 5 average rating, 22 reviews
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Top guest favourite
Home in Palgrave
Relaxing Luxury Palgrave Cottage w/pool on 3 acres
4 bedrooms, 5 beds
4–9 Oct
4.98 out of 5 average rating, 40 reviews
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Top guest favourite
Home in Bolton West
Perfect Group Getaway Large House with Style
6 bedrooms, 7 queen beds
1–6 Oct
5.0 out of 5 average rating, 11 reviews
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Home in Erin
Country Farm Stay in Erin, Ontario
4 bedrooms, 4 beds
1–6 Nov
New place to stay
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Top guest favourite
Flat in Brampton
Modern 2BR Suite • Near Pearson Airport/ Sleeps 4
2 bedrooms, 2 queen beds
4–9 Oct
5.0 out of 5 average rating, 19 reviews
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Top guest favourite
Guest suite in Bolton West
Guests praise:Spotlessly Clean, SelfCheck-In, WiFi
2 bedrooms, 2 queen beds
3–8 Oct
4.99 out of 5 average rating, 94 reviews
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Guest favourite
Home in Mulmur
Experience peace in the rolling hills of Mulmur!
7 bedrooms, 9 beds
4–9 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Townhouse in Orangeville
Lightweight Townhouse
3 bedrooms, 3 queen beds
3–8 Oct
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Orangeville
The Blooming House
3 bedrooms, 4 beds
1–6 Oct
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Guest suite in Halton Hills
Heritage home with pool & huge garden
2 bedrooms, 2 beds
1–6 Oct
5.0 out of 5 average rating, 13 reviews
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Home in Brampton
Luxury Home in Mississauga Rd & Steeles
4 bedrooms, 6 beds
1–6 Oct
New place to stay
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Home in Bradford West Gwillimbury
Brightstone Family Retreat | 6BR • Sleeps 16 or
6 bedrooms, 9 beds
26–31 Oct
New place to stay
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Home in Caledon
A comfortable peaceful home!
3 bedrooms, 3 queen beds
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Home in Caledon
Private Winter Wonderland
4 bedrooms, 7 beds
1–6 Dec
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Home in Brampton
A Castle in Brampton, On., 3 Acres 17,000 sq. ft.
12 bedrooms, 12 queen beds
15–20 Oct
4.18 out of 5 average rating, 11 reviews
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Top guest favourite
Guest suite in Orangeville
"Country Escape" Guest Suite
2 bedrooms, 3 beds
1–6 Oct
4.97 out of 5 average rating, 78 reviews