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$950 & up -- Jamaica: 7-Nt. Packages from Toronto
Source: Expedia.ca | By Catherine Cunningham

Depart from Toronto for a week of sun and relaxation at a resort in Jamaica.
January 12; surrounding dates available

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Source: iCruise.com

Norwegian has never offered a package with so many extras: unlimited drinks, specialty dining, a pre-cruise hotel stay, transfer & $100 onboard credit
Select July-November dates

 
Source: Gate 1 Travel

Jet off to Iceland -- "one of the most dramatic natural spectacles on the planet" says Fodor's
Select dates January-March

 
Source: Transat Holidays

Spend seven days soaking up the sun in St. Martin, and perhaps do a bit of snorkeling or diving - there are about 50 unique dive locations in the area
Select dates January-March

 
Source: Indus Travels

This is definitely a trip to cross off the bucket list - 3 nights in Dubai and 4 nights in the beautiful Maldives
April-May; February-March also discounted

 
Source: itravel2000

Soak up the sun in Punta Cana with packages that include accommodation, all meals, and air.
Select January-March dates

 
Source: Finest Playa Mujeres

Be one of the first to stay at this luxurious all-inclusive resort including peak-season dates.
April 12 - Aug. 22; +US$50 Feb. 12 - April 11

 
Source: Air Canada Vacations

Take advantage of the area's year-round great weather with this all-inclusive package that includes airfare, hotel, meals and drinks
Jan. 4; other dates also available

 
Source: Air Transat

Over these dates, hotels in Paris and London are often discounted and summer crowds are a dim memory
Select January-February departures

 
Source: Hurtigruten

Explore Norway, "one of the most beautiful places on Earth" (Huffington Post), with a deal that offers 50% savings on regular prices.
Depart select January-March dates

 
Source: Featured Destination: Aruba

Beachfront deals during peak season and Carnival
Deals through March

 
 
Daily through March
The ICON Hotel & Lounge
 
January 30; surrounding dates available
Expedia.ca
 
January 12; surrounding dates available
Expedia.ca
 
Select dates January-March
Air Canada Vacations
 
Select January-March departures
itravel2000
 
Select March dates
Cruise Connections Canada
 
Travel between Feb. 19-27, 2015
Flight Centre
 
Travel between May 1-10, 2015
Flight Centre
 
Depart between April 6-14, 2015
Flight Centre
 
 
Travel between Feb. 10 and Feb. 18, 2015
Flight Centre
 
Select departures April 12 - June 30
CheapCaribbean.com
 

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Hilary Solan — Travel, Entertainment and Local Deal Expert
Hilary Solan
Deal Expert, Chicago
From discounted park passes to hotel stays, here's how to save a few bucks. More