Caledon Vacations from $781

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Your Caledon Vacation

Entertainment, history, art and more … It's all waiting for you with a Caledon vacation package. And with the ability to easily customize your city getaway, you know it'll be one that's difficult to forget. If your trip to Caledon includes a little sightseeing, visit well-known attractions like Caledon Country Club, Downeys Farm Market and Cheltenham Badlands. Don't put off your visit to this city any longer. The ultimate Caledon vacation is a few quick clicks away with Expedia.

The Latest Caledon vacation packages

Price found within the past 48 hours. Click for updated prices.
New 3BR Townhouse, Minutes to Niagara Falls and Brock University by GLOBALSTAY

New 3BR Townhouse, Minutes to Niagara Falls and Brock University by GLOBALSTAY

4 out of 5
Save 100% on your flight
Price was $1,193, price is now $781 per person
$781
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Toronto (YYZ)
8.6/10 Excellent! (22 reviews)
The house its-self was beautiful! Location was convenient. However, I've never stayed in a place that house keeping doesn't check the dishwasher and drier before the next tenant. Showed up at 7pm to a dishwasher full of "clean dishes" that still had food all over them. And their trash was still there. I emailed them to let them know about dishes and trash so I wouldn't get charged. They seemed confused about my complaint. Sure enough when we left we got charged for some of the last tenants garbage.

Reviewed on Aug 25, 2025

City Centre Suites

City Centre Suites

3.5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $1,285, price is now $799 per person
$799
per person
Dec 28 - Jan 2
found 8 hours ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
9.2/10 Wonderful! (7 reviews)
Excellent location , very walkable to everything we wanted to do ! Property it’s self was ok .. one bed broke, window in master bed wasn’t operational , freezer had been left open

Reviewed on Oct 6, 2025

GLOBALSTAY. Modern North York Condos

GLOBALSTAY. Modern North York Condos

4 out of 5
North York
Save 100% on your flight
Price was $1,390, price is now $871 per person
$871
per person
Dec 26 - Dec 30
found 7 hours ago
Roundtrip flight included
New York (NYC) to Toronto (YYZ)
6.8/10 (151 reviews)
This was my first GloblalStay stay and so the model was a little of a mystery and took some work to figure out its unique rules. I did eventually get on track. It's a great bargain compared to the other options I was looking at in Toronto. The place was immaculate and the ability to park in the building was a plus. The kitchen was useful. Everything I needed was there. Plus a balcony! Great value.

Reviewed on Oct 11, 2025

GLOBALSTAY. Luxury 3BR Townhomes with HOT TUB, Gym, BBQ

GLOBALSTAY. Luxury 3BR Townhomes with HOT TUB, Gym, BBQ

4 out of 5
Stoney Creek
Save 100% on your flight
Price was $1,320, price is now $861 per person
$861
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Hamilton (YHM)
5.8/10 (6 reviews)
I like this property I like it it’s very clean

Reviewed on Nov 26, 2024

GLOBALSTAY. Elegant Downtown Apartments

GLOBALSTAY. Elegant Downtown Apartments

4 out of 5
Downtown Toronto
Save 100% on your flight
Price was $1,792, price is now $1,173 per person
$1,173
per person
Dec 28 - Jan 2
found 8 hours ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
7.4/10 Good! (402 reviews)
Very beautiful condo with amazing views. They were very accommodating to us. Will definitely recommend to family and friends and we will definitely be back.

Reviewed on Oct 16, 2025

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Discover the most popular places to visit in Caledon

Rogers Centre which includes signage and a city

Rogers Centre

Come to this multipurpose stadium to watch baseball matches and football games, listen to concerts of famous bands, see family shows or simply tour this central entertainment complex.

Rogers Centre
CN Tower showing skyline, a city and modern architecture

CN Tower

Take the glass elevator to the lookout points on Toronto’s iconic landmark to enjoy views as far as Niagara Falls or have dinner in high style.

CN Tower
CN Tower which includes rides

Canada's Wonderland

The highlight at this amusement park is the super-fast Leviathan ride, but there are 15 other roller coasters and more than 200 attractions to explore.

Canada's Wonderland

What to do in Caledon

Toronto: Casa Loma Entry Ticket

Toronto: Casa Loma Entry Ticket

$29
per adult
86% of travellers recommend
Toronto: Casa Loma Entry Ticket
Toronto: Ripley's Aquarium of Canada Entry Ticket

Toronto: Ripley's Aquarium of Canada Entry Ticket

$33
per adult
90% of travellers recommend
Toronto: Ripley's Aquarium of Canada Entry Ticket
The highlight of any visit to the Hockey Hall of Fame is the Esso Great Hall, where guests can get close up to hockey's greatest treasure, the Stanley Cup.

Hockey Hall of Fame Admission Ticket

$18
per adult
90% of travellers recommend
Hockey Hall of Fame Admission Ticket
See all activities in Caledon

Caledon Hotel Deals

Great Canadian Casino Resort Toronto

Great Canadian Casino Resort Toronto

4 out of 5
1133 Queens Plate Dr, Toronto, ON
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $134 total per night from Oct 28 to Oct 29
$134 total
Oct 28 - Oct 29
Total with taxes and fees
8.8/10 Excellent! (4,294 reviews)
"Indoor pool with Hot tub and steam room were very nice!"

Reviewed on Oct 16, 2025

Great Canadian Casino Resort Toronto
Holiday Inn Toronto - Int'l Airport by IHG

Holiday Inn Toronto - Int'l Airport by IHG

3.5 out of 5
970 Dixon Rd, Toronto, ON
Fully refundable
$91 nightly
The price is $111 total per night from Nov 16 to Nov 17
$111 total
Nov 16 - Nov 17
Total with taxes and fees
8.2/10 Very Good! (2,036 reviews)
"Clean room and nice staff"

Reviewed on Oct 13, 2025

Holiday Inn Toronto - Int'l Airport by IHG
Embassy Suites by Hilton Toronto Airport

Embassy Suites by Hilton Toronto Airport

3.5 out of 5
262 Carlingview Dr, Toronto, ON
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $139 total per night from Nov 2 to Nov 3
$139 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (2,078 reviews)
"Pretty much fine. Staff is awesome. Breakfast is also good. Nice hotel for this price"

Reviewed on Oct 13, 2025

Embassy Suites by Hilton Toronto Airport
See all 2,933 properties in Caledon
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.

Caledon Essential Information

Language
English
Currency
Canadian dollars
Closest Airport
Pearson Intl. Airport (YYZ)
Max Temp Winter
25ºF
Max Temp Summer
75ºF
Top Sights
Rose Theatre, Lester B. Pearson Memorial Theatre and Osprey Valley Golf

Caledon Ski Vacation Packages

Go your own way with one of our Caledon ski vacation packages. Whether you're into thrills on the mountain, tranquility at altitude or a little of both, your perfect escape starts with Expedia. Among the top snow sports destinations in Canada, Caledon has around 26 ski runs operating between November and March each year. Enjoy a little time in the ski village and grab any gear you need for downhill skiing. If it's your first time on skis, there's at least one beginners' area where you can learn the basics. When you're ready to leave the slopes, head on over to the wellness center and spa here. It's an ideal spot to relax after a big day of downhill action. The whole crew will have a blast on your family ski vacation in Caledon, with awesome activities such as hiking, snow biking and snowshoeing also up for grabs.

How To Get Around

Many visitors who book one of our Caledon vacation packages jet into Toronto Pearson International Airport. From there, it's 45 minutes before you're hitting the slopes of Caledon's most exciting runs. From the middle of Caledon, the ski slopes are around 30 minutes away by car and free parking is available. During winter months, it's best to bring tire chains. Pick from half-day, weekend-pass and full-day tickets depending on your ski vacation budget and plans. When it comes to budgets, Expedia's Caledon ski package deals will help you stay within yours. Combine your flight, hotel and car rental and see the savings pile up like snow after a big storm.

Caledon Resort Ski Info

Elevation of lowest ski lift
1,082 ft
Cost of 1-day lift pass
Under $75
Easy runs
7
Moderate runs
8
Advanced runs
8
Longest run
0.27 mi

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Frequently asked questions

How much does a Caledon vacation package cost?
Offering excellent value package deals from $781 on Expedia, you'll be surprised at how little a vacation to Caledon costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Caledon?
You're likely to find lower rates and greater availability in November, December and January. Browse our cheap Caledon vacation packages and you could score some excellent off-season deals.
How many days is enough for Caledon?
Typically, a handful of days is enough to go to the main sights during your Caledon vacation. However, if you want to have more time to relax or take day tours, consider extending your itinerary.
How to find the best Caledon package deals?
Start your search for a Caledon package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Caledon package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Caledon adventure off to a flying start.
Is it cheaper to book a Caledon vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component individually. And you'll still have the flexibility to create a personalized Caledon vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Caledon?
Land incredible bargains by booking your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Caledon adventure.
How to plan a trip to Caledon?

  1. Choose when to travel: Check your calendar and get packing. Your preferred time of year and the available activities will also help you decide when to vacation in Caledon.
  2. Budget wisely: As well as the cost of your stay, you should consider other expenses. These include food, transportation and flights. Also, set aside a little extra for unexpected costs that could arise during your trip to Caledon.
  3. Organize your Caledon escape with Expedia's trip planning tool: Search for and book accommodations and experiences all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Caledon together.
  4. Set the duration of your trip: Start by compiling a list of the activities and sights you'd like to get to in Caledon. Then, estimate how long you'll need for each, including any travel time.
  5. Combine your airfare and accommodations: Once you've settled on your travel dates and duration, lock in the ideal Caledon vacation package for you.
  6. Add on excursions and experiences: Read our dedicated travel guide to find some fun things to do in Caledon. Book tickets or make reservations in advance to save time and avoid the stress of trying to find activities when you arrive.

Does Expedia offer Book Now, Pay Later Caledon vacation packages?
If you're anything like us, you love jet-setting around the world but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the overall cost of your Caledon break across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you spot them.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.