Monthly Rentals in Caledon

Discover long-term rentals that feel like home for stays of a month or longer.

Nearby monthly rentals

Top guest favorite
Home in Erin
5 out of 5 average rating, 62 reviews

Stonewell Farm Guest House

DanaRating, 5 stars6 months ago
We had a lovely stay at Lee Anne’s place. The pictures really don’t do it justice. The rooms were so comfortable! The beds were dressed with beautiful quality pillows and linens. The kitchen had all the appliances and dishes you will need to entertain a dozen people. The fireplace is positively magnificent and there was plenty of dry wood just outside the door to enjoy it. The grounds are meticulously well kept and Lee Anne’s husband Tom was a pleasure to chat with. This property in the fall is stunning but I can’t imagine any season that would not be amazing here. All in all it was an incredible week in this beautiful home and we would not hesitate to rent it again. Thank you so very much Lee Anne!
Guest favorite
Apartment in Caledon
4.94 out of 5 average rating, 82 reviews

Separate apartment with pool, on golf course.

FeonaghRating, 5 stars2 days ago
Just perfect for when showing at Caledon Equestrian Park. 7 minute drive.
Guest favorite
Apartment in Caledon
4.82 out of 5 average rating, 202 reviews

Basement for Rent Bolton South Hill

ShannonRating, 5 stars1 week ago
Exactly as pictured and described. Very convenient location and responsive hosts
Top guest favorite
Bungalow in Terra Cotta
4.99 out of 5 average rating, 114 reviews

Country Cottage House, Cozy and Private

HannahRating, 5 stars3 weeks ago
With this being our third stay at Doug’s peacefully and private Airbnb, i’m sure you can guess that I have nothing but amazing things to say! They house is clean and well kept, after our easy no contact entry we were greeted with a kindly written card and a lovely bottle of wine left for us by Doug. We spent 3 days relaxing in the well-maintained hot tub, enjoying the lovely warmth of the fresh linens and unwinding well watching tv on the large screen tv in the living room. We ordered pizza from a recommendation given by Doug and a few others who have staid in this Airbnb (written in a guest book filled with nothing but positive reviews) If you are interested in the perfect, private Airbnb. This is the place to be!

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term vacation rentals and a single monthly payment without additional charges.*

Book with confidence

Reviewed by our trusted community of guests and 24/7 support during your extended stay.

Work-friendly spaces for digital nomads

Traveling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.

Looking for serviced apartments?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing, and relocation needs.

Stay near Caledon's top sights

Hockley Valley Resort - Golf, Spa and Ski35 locals recommend
Onthe95 locals recommend
Fortinos4 locals recommend
Alton Mill Arts Centre8 locals recommend
Cheltenham Badlands31 locals recommend
Domino's Pizza33 locals recommend

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.