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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 $661, price is now $482 per person

$482

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 $2,129, price is now $1,333 per person

$1,333

per person

Aug 26 - Aug 30

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.

Absolutely stunning hotel. Amazing rooftop pool. Delicious restaurants and cocktail bar. Perfect choice for a girlfriend’s getaway.

Reviewed on Jul 18, 2026

Hilton Toronto/Markham Suites Conference Centre & Spa

4 out of 5

Price was $1,218, price is now $802 per person

$802

per person

Sep 27 - Oct 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Toronto (YYZ)

Book a stay at this spa hotel in Markham. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Flato Markham Theatre and First Markham Place are located nearby.

Good

Reviewed on Jul 17, 2026

Hotel Riu Plaza Toronto

4 out of 5

Price was $913, price is now $658 per person

$658

per person

Aug 17 - Aug 20

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.

Plush Hotel

2 out of 5

Price was $950, price is now $703 per person

$703

per person

Aug 28 - Aug 31

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Toronto (YYZ)

Stay at this hotel in Toronto. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Rogers Centre and CN Tower are located nearby.

Location was great and with in walking distance so we didn’t have to drive . Staff was very helpful . The chef (Richard )in the cafe was great . The woman who helped me with parking ( may have been the manager )was also awesome because parking was expensive if you payed by the hour …

Reviewed on Jun 29, 2026

Embassy Suites by Hilton Toronto Airport

3.5 out of 5

Price was $964, price is now $718 per person

$718

per person

Sep 27 - Oct 3

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 free airport shuttle. Our guests praise the breakfast and the bar in our reviews. Popular attractions Woodbine Racetrack and Casino Woodbine are located nearby.

A perfect stay.

Reviewed on Jul 17, 2026

Holiday Inn Express Toronto - Downtown by IHG

3 out of 5

Price was $1,539, price is now $1,167 per person

$1,167

per person

Sep 27 - Oct 3

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 fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions CF Toronto Eaton Centre and Scotiabank Arena are located nearby.

One King West Hotel & Residence

4 out of 5

Price was $865, price is now $663 per person

$663

per person

Sep 4 - 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, room service, and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Scotiabank Arena and CF Toronto Eaton Centre are located nearby.

Room was clean. Hotel is older. Staff was nice.

Reviewed on Jul 18, 2026