Photo by ‎‎‎‎‎‎Princess Garcia

Search Vacation Homes in Caledon

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Caledon

Exquisite Vintage Hotel - Steps to Downtown

10.0 out of 10, Exceptional, (5)
Exquisite Vintage Hotel - Steps to Downtown

A Modern Private Basement Suite – Richmond Hill

10.0 out of 10, Exceptional, (1)
"Had an incredible stay. Communication was great, they were very understanding that we were at Canadas Wonderland for the day and would be checking in late. Everything was exactly like they had advertised. Would definitely recommend. "
$134 nightly
The price is $152
Aug 24 - Aug 25
Total includes taxes and fees
A Modern Private Basement Suite – Richmond Hill

EXCLUSIVE Luxury Brand New 3-bedroom townhome: Family friendly in Kleinburg

8.0 out of 10, Very Good, (6)
EXCLUSIVE Luxury Brand New 3-bedroom townhome: Family friendly in Kleinburg

Charming bungalow in lovely Richmond Hill with AC, WiFi

8.4 out of 10, Very Good, (7)
"Highly recommend, will come again"
$129 nightly
The price is $146
Aug 31 - Sep 1
Total includes taxes and fees
Charming bungalow in lovely Richmond Hill with AC, WiFi

Spacious home in Mississauga with pool table in the basement.

9.6 out of 10, Exceptional, (4)
$147 nightly
The price is $167
Aug 27 - Aug 28
Total includes taxes and fees
Spacious home in Mississauga with pool table in the basement.

The Artist House in Downtown Richmond Hill [2bdrm|1 bath]

9.6 out of 10, Exceptional, (45)
"Host was very kind "
The Artist House in Downtown Richmond Hill [2bdrm|1 bath]

LAKESHORE Port Credit Is One Of The Few Truly Walk Able area In Mississauga.

9.2 out of 10, Wonderful, (27)
"We had a wonderful time at our Vrbo! We just had a little trouble finding the lock box at first but other than that it was such a fun experience."
LAKESHORE Port Credit Is One Of The Few Truly Walk Able area In Mississauga.

Luxury 2BR - Pool/Gym/Sauna - 1 min to Subway

10.0 out of 10, Exceptional, (17)
"Great location and clean place. Will stay again. "
$371 nightly
The price is $447
Aug 17 - Aug 18
Total includes taxes and fees
Luxury 2BR - Pool/Gym/Sauna - 1 min to Subway

Luxurious Spacious Dream Home with Parking!

8.6 out of 10, Excellent, (9)
"Clean, sleek, and large—fully detached house. Host was communicative, accommodating, and nice through the entire process."
$218 nightly
The price is $246
Aug 26 - Aug 27
Total includes taxes and fees
Luxurious Spacious Dream Home with Parking!

5 cozy bedrooms include 7 bed near Heartland Plaza and Outlet Malls

8.4 out of 10, Very Good, (11)
"great place "
$462 nightly
The price is $522
Sep 12 - Sep 13
Total includes taxes and fees
5 cozy bedrooms include 7 bed near Heartland Plaza and Outlet Malls

“Your Countryside Retreat – Our Passion” 🌿🏡 🛏️ Cozy Comfort | Rustic Charm

10.0 out of 10, Exceptional, (3)
"Great value for the location. Nice neighborhood and proper amenities. "
$105 nightly
The price is $119
Sep 3 - Sep 4
Total includes taxes and fees
“Your Countryside Retreat – Our Passion” 🌿🏡 🛏️ Cozy Comfort | Rustic Charm

The Caledon Retreat

10.0 out of 10, Exceptional, (2)
"amazing stay , great communication, beautiful house , had many assets to make your stay comfortable will definitely be coming back !"
$581 nightly
The price is $656
Aug 21 - Aug 22
Total includes taxes and fees
The Caledon Retreat

Modern & Cozy 1BR w/ parking by Square One

8.0 out of 10, Very Good, (2)
"Great location, lots to do, hosts were very helpful. Wasn't very clean, had to do a garbage run before settling in and dishes were left dirty from the last guest. This isn't on the host at much at the cleaners hired. The building is getting worn down. Hot tub broken while we were there. It's not a 5-star stay, but good enough for a couple guys needing a central place to sleep."
$203 nightly
The price is $229
Aug 18 - Aug 19
Total includes taxes and fees
Modern & Cozy 1BR w/ parking by Square One

Clean, Cozy & Spacious Suite + Private Bathroom near Toronto Airport !

7.2 out of 10, Good, (38)
"Communication was easy and nina was very accommodating. Place was clean and tidy and convenient for situation. Family was very friendly. However, keep in mind there is no kitchen which was not a big deal for me but for future guest who are looking for a room and want to cook. Regardless, would recommend people to stay. "
$63 nightly
The price is $71
Aug 24 - Aug 25
Total includes taxes and fees
Clean, Cozy & Spacious Suite + Private Bathroom near Toronto Airport !

The Residence, your comfort is our culture

10.0 out of 10, Exceptional, (1)
"This property was quite adequate for our 3 day stay in Oakville. "
$191 nightly
The price is $216
Aug 25 - Aug 26
Total includes taxes and fees
The Residence, your comfort is our culture

Newly renovated 2-story house with 5 bed rooms and 4 washrooms

9.6 out of 10, Exceptional, (7)
"Clean, well maintained, timely communication, quiet neighborhood. Accurate description. Love our stay. Thank you Gracy"
Newly renovated 2-story house with 5 bed rooms and 4 washrooms

Private home with large bedroom and spacious common areas with patio.

9.0 out of 10, Wonderful, (8)
"The place was good. House was clean when we arrived and it was near a few malls. "
Private home with large bedroom and spacious common areas with patio.

Private Boyne River Cottage- steps to great fishing

Private Boyne River Cottage- steps to great fishing

Entire place, Ground level walkout Basement with Huge backyard

7.0 out of 10, Good, (21)
"It was an odd setup but worked for our needs"
$107 nightly
The price is $121
Aug 15 - Aug 16
Total includes taxes and fees
Entire place, Ground level walkout Basement with Huge backyard

Beautiful basement in friendly neighbourhood

Beautiful basement in friendly neighbourhood
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Caledon Hotel Reviews