
Holiday rentals in Caledon
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Top-rated holiday rentals in Caledon
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Other great holiday rentals in Caledon
Superhost

Home in Brampton
4.75 out of 5 average rating, 4 reviewsMy Charming Getaway
MichelleRating, 5 stars8 months ago
The unit was as described in the ad. Very clean and well maintained. The host followed up to ensure we were checked in ok and she always responded in a timely manner. .
Superhost

Home in Pickering
4.77 out of 5 average rating, 79 reviewsBeach House: First Floor
TennieRating, 5 stars1 week ago
Very nice apartment and we felt very welcomed - the walk by the water and the area was beautiful. So nice and friendly and would love to stay again next time we stop by. Nice furniture, bedding , comfortable bed , bathroom - everything we needed was available for us to use.
Guest favourite

Townhouse in Richmond Hill
5 out of 5 average rating, 12 reviewsCheerful 3 bedrooms townhouse
SabrinaRating, 5 stars7 months ago
Great airbnb - would recommend! Stayed for 8 months and was good for our family with two small kids! Three large bedrooms (one in basement) and one office upstairs, all amenities were provided - plenty of kitchen utensils, plates, lots of baby things (high chair, brezza maker, safety gates), and well stocked. The location is nice - close to a huge park and community center with library and swimming pool (across one major road only!) and nice trail right behind. Close to Costco (7-8 mins) and lots of good restaurants within 10-15 mins drive :) ravine lot at the back so lots of privacy! Host, Eva, was super responsive and replied quickly, whenever there was any issues she replied asap, and was clear in all her instructions! Beautiful spacious airbnb , three floors and one basement , would recommend for any family !
Top guest favourite

Cabin in Holstein
4.99 out of 5 average rating, 109 reviewsKettle Creek Cabin
AlanRating, 5 stars3 weeks ago
This was our second time staying in Emily's cabin, and certainly not the last! The place was quiet, private, and with a rustic charm that was perfect for a group of admittedly very nerdy adults looking for a place to spend a weekend playing medieval fantasy tabletop roleplaying games. The place was quaint, clean, well stocked with supplies, very spacious, and Emily was very responsive if we needed anything. Though, as repeat customers, we needed very little. Thanks Emily, and with any luck, we'll be back soon.
Superhost

Villa in Burlington
4.66 out of 5 average rating, 38 reviewsGrand Villa Estate
SamanthaRating, 5 stars7 months ago
Huge beautiful space. Very clean. Host was excellent and very responsive and respectful. Would stay here again.
Superhost

Home in Midtown
4.7 out of 5 average rating, 93 reviewsStunning Bright 2+ Bdrm Luxury w/Free Parking
John And IlsaRating, 5 stars3 months ago
This is our second time staying here, and Arti's place was perfect for our group of 3 adults, a toddler and a baby. The Beltway proved to be a wonderful alternative to walking on icy sidewalks our first evening and had a wonderful peaceful ambiance as opposed to roads and traffic. The place is exactly as advertised and we would not hesitate to stay here again.
Guest favourite

Flat in Pickering
4.91 out of 5 average rating, 32 reviewsStunning 2 bedroom apt. W/ parking on site.
AndrewRating, 5 stars2 months ago
We had a wonderful stay at Rafeena’s place. The apartment was incredibly clean, beds were comfortable, kitchen decently equipped. High ceilings and large windows made a space feel airy and bright. The extra touches (fresh fruit, drinks) were a lovely touch after a long drive. Rafeena was very responsive and friendly. We highly recommend this bnb.
Guest favourite

Home in Scarborough
4.95 out of 5 average rating, 55 reviews"Home Sweet Home"
PhilipRating, 5 stars1 week ago
Jia is very friendly, responsive and provided us with everything we needed. The house location is great, only takes 5 to 10 minutes to decent restaurants. We would definitely rent her house again with my annual family reunions. Thank you Jia for a great host.
Quick stats about holiday rentals in Caledon
Total rentals
1.8K properties
Total number of reviews
33K reviews
Family-friendly rentals
600 properties are a good fit for families
Pet-friendly rentals
300 properties allow pets
Rentals with a pool
70 properties have a pool
Rentals with dedicated workspaces
890 properties have a dedicated workspace
Destinations to explore
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- Rentals with a firepit Caledon
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- Rentals with lake access Caledon
- Family-friendly rentals Caledon
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- Rogers Centre
- Scotiabank Arena
- CN Tower
- University of Toronto
- Blue Mountain Village
- Budweiser Stage
- Distillery District
- Port Credit
- Horseshoe Resort
- The Danforth Music Hall
- Metro Toronto Convention Centre
- Exhibition Place
- Toronto Zoo
- CF Toronto Eaton Centre
- TPC Toronto at Osprey Valley
- Massey Hall
- Royal Woodbine Golf Club
- Harbourfront Centre
- Whistle Bear Golf Club
- Snow Valley Ski Resort
- Yonge-Dundas Square
- Trinity Bellwoods Park
- Osler Bluff Ski Club
- Casa Loma