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Caledon Vacation Packages

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A terraced landscape with reddish soil, surrounded by green vegetation and trees.

Caledon
Toronto
Ontario
Canada
North America
Hotwire.com

Caledon Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

The Waterside Inn

3.5 out of 5

Price was $660, price is now $481 per person

$481

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

Book a stay at this business-friendly hotel in Mississauga. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Square One Shopping Centre and Port Credit Harbour Marina are located nearby.

1 Hotel Toronto

5 out of 5

Price was $2,185, price is now $1,323 per person

$1,323

per person

Sep 25 - Sep 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

Book a stay at this luxury hotel in Toronto. Enjoy free WiFi, an outdoor pool, and 3 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rogers Centre and CN Tower are located nearby.

Hotel Riu Plaza Toronto

4 out of 5

Price was $1,383, price is now $863 per person

$863

per person

Sep 25 - Sep 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

Book a stay at this business-friendly hotel in Toronto. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Popular attractions CN Tower and Rogers Centre are located nearby.

Shangri-La Toronto

5 out of 5

Save 100% on your flight

Price was $2,946, price is now $2,170 per person

$2,170

per person

Sep 1 - Sep 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

Book a stay at this luxury hotel in Toronto. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions CF Toronto Eaton Centre and CN Tower are located nearby.

Sterling Inn & Spa - an Ontario's Finest Inn

4 out of 5

Price was $714, price is now $527 per person

$527

per person

Aug 17 - Aug 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

Book a stay at this spa hotel in Niagara Falls. Enjoy free breakfast, a full-service spa, and room service. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Clifton Hill and Fallsview Indoor Waterpark are located nearby.

Was very impressed with our room, very clean and comfortable. Loved the steam shower. Breakfast was excellent, Staff were polite and very pleasant. My husband and I Enjoyed our stay, we will choose this hotel the next time we are in Niagara Falls.

Reviewed on Jul 17, 2026

Finlay House Bed and Breakfast Niagara - on - the - Lake

3.5 out of 5

Price was $940, price is now $705 per person

$705

per person

Aug 17 - Aug 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

Stay at this guesthouse in Niagara-on-the-Lake. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Shaw Festival Theatre and Peller Estates Winery are located nearby.

Staff were friendly and very accomodating.

Reviewed on Jul 16, 2026

Homewood Suites by Hilton Toronto Vaughan

3 out of 5

Price was $806, price is now $606 per person

$606

per person

Oct 4 - Oct 10

found 1 day ago

Roundtrip flight included

Fort Lauderdale (FLL) to Toronto (YYZ)

Book a stay at this business-friendly hotel in Vaughan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vaughan Mills Mall and Canada's Wonderland are located nearby.

Hotel was close to movie theater, shopping, restaurants. Staff was kind and helpful. Hotel had a big and delicious breakfast everyday. We had a 1 bedroom suite with kitchen which was convenient.

Reviewed on Jul 17, 2026

Cambridge Suites Toronto

4 out of 5

Price was $1,943, price is now $1,479 per person

$1,479

per person

Sep 1 - Sep 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

Book a stay at this business-friendly hotel in Toronto. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions CF Toronto Eaton Centre and Scotiabank Arena are located nearby.

Slightly odd room setup, which felt a bit cramped for our group of 5. The spellers was nice though, and they were great with helping us arrange parking, etc.

Reviewed on Jul 17, 2026