A red barn, a white church, and a horse in a grassy field with autumn trees.

Caledon Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Caledon vacation rentals

A backyard with a patio, a small shed, and a wooden fence.

1. Studio Apartment in the heart of Caledon

Studio Apartment in the heart of Caledon
CALEDON EAST
8.4 out of 10, Very good, (6 reviews)
"Beautiful flat !"
Canada
Jaivyn
$76 nightly
The price is $86
Oct 8 - Oct 9
Total with taxes and fees
Studio Apartment in the heart of Caledon
A neatly made bed with a patterned blanket, a bedside lamp, and a nightstand with a drawer.

2. Modern 2BR Private Suite |Prime Location

Modern 2BR Private Suite |Prime Location
Mayfield West
2.0 out of 10, (1 review)
"The host was asking for more money for no reason"
Canada
Pavit
$146 nightly
The price is $165
Oct 3 - Oct 4
Total with taxes and fees
Modern 2BR Private Suite |Prime Location
A modern kitchen with white cabinetry, a central island, and built-in appliances.

3. Caledon Estate

Caledon Estate
CALEDON
7.0 out of 10, Good, (2 reviews)
"Amenities were in extremely bad condition. Poor cleanliness than before. Often a go to spot for us. We invited our family and friends. They were not please with our communication and also on the experience."
United States
Rajesh B.
$721 nightly
The price is $815
Oct 3 - Oct 4
Total with taxes and fees
Caledon Estate
A modern living room with a grey sectional sofa, a round coffee table, and a large rug. There is a kitchen area with a dining table and chairs, a refrigerator, and a TV.

4. GLOBALSTAY Modern 3 BD House in Brampton

GLOBALSTAY Modern 3 BD House in Brampton
4.0 star property
Creditview
8.8 out of 10, Excellent, (40 reviews)
"Older property Clean"
Canada
Sukhdev
$289 nightly
The price is $340
Oct 4 - Oct 5
Total with taxes and fees
GLOBALSTAY Modern 3 BD House in Brampton
A kitchen with a white countertop, a toaster, and shelves with mugs and glassware.

5. Cozy 3BR Brampton

Cozy 3BR Brampton
3.0 star property
Fletcher's Meadow South
$204 nightly
The price is $240
Oct 5 - Oct 6
Total with taxes and fees
Cozy 3BR Brampton
A modern kitchen with a large island, bar stools, and a view through glass doors to an outdoor patio.

6. Walkout Basement with Private Entrance

Walkout Basement with Private Entrance
Rosedale Village
10.0 out of 10, Exceptional, (6 reviews)
"We had a Great stay and felt very welcome. I would recommend this VRBO."
United States
mark h.
$220 nightly
The price is $249
Oct 12 - Oct 13
Total with taxes and fees
Walkout Basement with Private Entrance
A modern living room with a grey sofa, a coffee table, and a TV mounted on the wall.

7. STUNNING & SPACIOUS 1 BEDROOM OASIS

STUNNING & SPACIOUS 1 BEDROOM OASIS
Deerfield
9.6 out of 10, Exceptional, (15 reviews)
"Property was well cared for and clean, checking in was straightforward and all necessary amenities were provided. Highly recommended"
United Kingdom
Parminder
$148 nightly
The price is $167
Nov 1 - Nov 2
Total with taxes and fees
STUNNING & SPACIOUS 1 BEDROOM OASIS
A wooden deck with chairs and tables overlooking a lake, a flag, and a gazebo.

8. Lakeview private suite with kitchen (Twin or King)

Lakeview private suite with kitchen (Twin or King)
Loretto
8.6 out of 10, Excellent, (8 reviews)
"Beautiful spot to stay! Highly recommended "
United States
Patrick S.
$125 nightly
The price is $141
Oct 4 - Oct 5
Total with taxes and fees
Lakeview private suite with kitchen (Twin or King)
A modern kitchen with a built-in oven, microwave, and stove. There is a dining area with a round table and two chairs. A black sofa and a small side table are in the living area.

9. The Perfect Getaway

The Perfect Getaway
Orangeville
7.8 out of 10, Good, (9 reviews)
"britney was great.she put one more bed for us so we can all sleep cpmfprtably.the loction os great.it was nice and cozy"
Canada
???? ?.
$194 nightly
The price is $219
Oct 9 - Oct 10
Total with taxes and fees
The Perfect Getaway
A modern kitchen with white cabinets, a wooden island, stainless steel appliances, and a bar stool.

10. Cozy Basement Apartment (700 sq ft) with Full Kitchen

Cozy Basement Apartment (700 sq ft) with Full Kitchen
Orangeville
9.0 out of 10, Wonderful, (2 reviews)
"Great location!"
Canada
Kefa
$111 nightly
The price is $125
Oct 31 - Nov 1
Total with taxes and fees
Cozy Basement Apartment (700 sq ft) with Full Kitchen
A modern kitchen with white cabinets, a stainless steel refrigerator, a coffee maker, and a dining area with a table and chairs.

11. The Grassy Oasis - Garden Suite | King Bed | Detached | Self contained

The Grassy Oasis - Garden Suite | King Bed | Detached | Self contained
Downtown Brampton
10.0 out of 10, Exceptional, (6 reviews)
"Everything was perfect and as noted in ad"
Canada
Rachel A.
$199 nightly
The price is $224
Oct 3 - Oct 4
Total with taxes and fees
The Grassy Oasis - Garden Suite | King Bed | Detached | Self contained
A living room with a dark wood floor, a red leather sofa, a glass coffee table, and a white door.

12. Affordable Quiet 3 Bdrms + 2.5 bath Home in Toronto Area

Affordable Quiet 3 Bdrms + 2.5 bath Home in Toronto Area
Royal Orchard
8.0 out of 10, Very good, (50 reviews)
"Very accomadating"
United States
Tiffany N.
$195 nightly
The price is $220
Oct 4 - Oct 5
Total with taxes and fees
Affordable Quiet 3 Bdrms + 2.5 bath Home in Toronto Area
A spacious living area with a wooden floor, a grey sofa, a wooden coffee table, and a staircase with a railing.

13. GlobalStay 4 Bedrooms House in Brampton

GlobalStay 4 Bedrooms House in Brampton
4.0 star property
Brampton
8.0 out of 10, Very good, (3 reviews)
"Great stay, no complaints"
Canada
Chris
$338 nightly
The price is $397
Oct 18 - Oct 19
Total with taxes and fees
GlobalStay 4 Bedrooms House in Brampton
A pathway leading to a house with a separate entrance.

14. Zen Nest - Cozy, conveniently located, and just minutes to the airport!

Zen Nest - Cozy, conveniently located, and just minutes to the airport!
Ebenezer East
8.8 out of 10, Excellent, (13 reviews)
"It was a very nice place to stay. The communication was great with the host for everything that we needed."
United States
Mariah D.
$168 nightly
The price is $190
Oct 12 - Oct 13
Total with taxes and fees
Zen Nest - Cozy, conveniently located, and just minutes to the airport!
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

15. Charming Erin Country House near downtown

Charming Erin Country House near downtown
Erin
7.4 out of 10, Good, (13 reviews)
"Beautiful home, very clean and comfortable. Would definitely stay again!"
Canada
Nancy B.
$249 nightly
The price is $281
Oct 7 - Oct 8
Total with taxes and fees
Charming Erin Country House near downtown
A compact kitchen with white cabinets, a black refrigerator, a microwave, a coffee maker, and a stove.

16. Red-Roof Stay self Check-In-Near Pearson Airport

Red-Roof Stay self Check-In-Near Pearson Airport
Malton
10.0 out of 10, Exceptional, (1 review)
"Everything was perfect"
United States
Jose Miguel
$174 nightly
The price is $197
Oct 3 - Oct 4
Total with taxes and fees
Red-Roof Stay self Check-In-Near Pearson Airport
A two-story brick house with a patio area.

17. Entire place, Ground level walkout Basement with Huge backyard

Entire place, Ground level walkout Basement with Huge backyard
Orangeville
7.4 out of 10, Good, (40 reviews)
"Loved our accommodations! Exactly what we were looking for! Will book next year! Thank you!"
Canada
Darlene M
$103 nightly
The price is $117
Oct 3 - Oct 4
Total with taxes and fees
Entire place, Ground level walkout Basement with Huge backyard
A modern kitchen with grey cabinets, stainless steel appliances, and a white countertop.

18. Elegant 2 Bedroom Guest Suit

Elegant 2 Bedroom Guest Suit
New Springbrook
8.8 out of 10, Excellent, (16 reviews)
"We stayed there as a family for two nights. Everything was fine. The hosts were very friendly and responded quickly to all our queries. The only thing, in my opinion, is that a bit more attention could be paid to cleanliness. The bathroom and kitchen (especially the microwave) need a bit of a spot of a clean."
Canada
Olena
$125 nightly
The price is $141
Oct 4 - Oct 5
Total with taxes and fees
Elegant 2 Bedroom Guest Suit
A modern kitchen with dark cabinetry, stainless steel appliances, and a tiled backsplash.

19. Cozy 1-bedroom with WiFi and AC in charming private location

Cozy 1-bedroom with WiFi and AC in charming private location
New Springbrook
10.0 out of 10, Exceptional, (2 reviews)
"Parking was easy. The room is big enough for two people and is clean and organized. However, the restroom is quite small and crammed. It has everything that you need from WiFi to a fridge/freezer, electric stove tops and pots for cooking, and plates and utensils. There’s also a TV for YouTube and Netflix. The owner is very responsive and nice as well :)"
United States
Khang
$214 nightly
The price is $242
Oct 3 - Oct 4
Total with taxes and fees
Cozy 1-bedroom with WiFi and AC in charming private location
A snow-covered landscape with a cabin featuring a deck, outdoor seating, and string lights.

20. Hockley Riverside Cottage • Loft & Bunkie

Hockley Riverside Cottage • Loft & Bunkie
Mono
10.0 out of 10, Exceptional, (29 reviews)
"wonderful time at the cabin after my wedding! perfect size and location. nice little getaway."
United States
Sabrina s.
Hockley Riverside Cottage • Loft & Bunkie
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.
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Top Caledon Hotel Reviews

Sandman Signature Mississauga Hotel

Sandman Signature Mississauga Hotel

10/10 Excellent
"Sandman is a clean, safe and modern hotel. Really enjoyed the attached restaurant Denny's. Good food, good service. And appreciated the 24 hour shuttle service to YYZ. It is a hotel I would recommend."
Patricia 1-night trip
Posted less than an hour ago
Sandman Signature Mississauga Hotel

Find out more about Caledon

Everything you need to know about Caledon vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Caledon vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Caledon vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Caledon vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Caledon. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Caledon in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $141 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Caledon rentals

At Expedia, we put the best Caledon vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Caledon rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Caledon vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Caledon. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Caledon?

Yes, you can find vacation rentals in Caledon near Alton Mill Arts Centre, or you can choose a more remote option if you're looking for a relaxing stay. Discover why Caledon is known for its spas. Make sure you have time to check out the golf courses and waterfalls during your trip.

What's the top vacation rental in Caledon?

Elegant 2 Bedroom Guest Suit: This vacation home rental outside of Caledon is equipped with a selection of games, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Caledon?

Choose from 49 Expedia vacation rentals in Caledon for a memorable vacation.

What’s there to see and do in Caledon?

Cheltenham Badlands and Albion Hills Conservation Area are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find popular places like Canada's Wonderland and Vaughan Mills Mall.

What’s a vacation rental in Caledon like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Caledon. Vacation rentals feature extras like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for families.