All-Inclusive
Punta Cana
Dominican Republic
Ocean El Faro
4.54.5 star hotelFrom Toronto (YYZ)
Air Canada Vacations · Direct flightDeparts Thu, Feb 11
- 7 nights
- Junior Suite Nature View
- Flights incl.
FromCA $585/ person · incl taxes & fees
Winter Vacation Deals
Book by August 31 and save an extra $100 with code SUN100.
Top winter vacation deals
Explore hand-picked winter packages to warm-weather favourites across Mexico, the Caribbean and beyond.
Winter packages by departure city
Live packages by departure city — flights, hotel and transfers in one price.
Flying from
Air Canada Vacations · Direct flight
All-Inclusive
Punta Cana
Dominican Republic
El Beso Adults Only At Ocean El Faro
4.54.5 star hotelFrom Toronto (YYZ)
Sunwing Vacations · Direct flightDeparts Fri, Feb 5
- 7 nights
- El Beso Junior Suite Pool Gardenview
- Flights incl.
FromCA $594/ person · incl taxes & fees
Room Only
Cancun
Mexico
Smart Cancun
44 star hotelFrom Toronto (YYZ)
Sunwing Vacations · Direct flightDeparts Wed, Sep 23
- 7 nights
- Smart Room
- Flights incl.
FromCA $915/ person · incl taxes & fees
All-Inclusive
Cancun
Mexico
Melia Casa Maya
44 star hotelFrom Toronto (YYZ)
WestJet Vacations · Direct flightDeparts Wed, Oct 7
- 8 nights
- The Level Suite Swim Up Balcony
- Flights incl.
FromCA $1,007/ person · incl taxes & fees
Room Only
Punta Cana
Dominican Republic
Reserva Real By Harper
4.54.5 star hotelFrom Toronto (YYZ)
Air Canada Vacations · Direct flightDeparts Tue, Nov 17
- 7 nights
- Run Of The House
- Flights incl.
FromCA $1,049/ person · incl taxes & fees
All-Inclusive
Puerto Vallarta
Mexico
Krystal Puerto Vallarta
44 star hotelFrom Toronto (YYZ)
Air Canada VacationsDeparts Tue, Nov 17
- 8 nights
- Deluxe Mountain View
- Flights incl.
FromCA $1,049/ person · incl taxes & fees
All-Inclusive
Punta Cana
Dominican Republic
Vik Hotel Arena Blanca
44 star hotelFrom Toronto (YYZ)
Transat Holidays · Direct flightDeparts Mon, Nov 2
- 7 nights
- Room Gardenview
- Flights incl.
FromCA $1,110/ person · incl taxes & fees
All-Inclusive
Puerto Plata
Dominican Republic
Marien Puerto Plata Hotel
44 star hotelFrom Toronto (YYZ)
Sunwing Vacations · Direct flightDeparts Fri, Oct 30
- 7 nights
- Deluxe Gardenview Double
- Flights incl.
FromCA $1,119/ person · incl taxes & fees
Transparent pricing
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Reviewed by the shoptravel team
Chosen and checked by shoptravel travel advisors.
Escape the Canadian winter
Swap short, cold days for warm sunshine. A winter vacation gives you the mid-season reset that makes the rest of winter easier.
Choose your kind of escape. Unwind at an all-inclusive resort, explore a new city or settle into a beachfront hotel with nothing on the schedule.
Packages keep planning simple. Bundle your flight and hotel in one booking, with options for different budgets, travel dates and departure cities.
Where to go for winter sun
Mexico and the Caribbean are classic winter favourites for good reason: warm weather, beautiful beaches and convenient flights from Canada. Choose Cancun or Riviera Maya for resorts and nightlife, Punta Cana for long beaches and easy all-inclusive stays, or Cuba and Jamaica for laid-back island time. For something different, look to Florida, Costa Rica or destinations farther south where summer is just beginning.
More seasonal getaways
Winter vacations FAQ
Where is the best place to vacation in winter?
Mexico, the Dominican Republic, Cuba and Jamaica are among the most popular warm-weather winter destinations for Canadians. The best choice depends on your budget, departure city and whether you prefer beaches, activities, nightlife or a quiet resort.
When should I book a winter vacation?
For the best selection, book three to six months before departure. Christmas, New Year and March break dates sell quickly, while travellers with flexible dates may find last-minute offers outside peak periods.
What is included in a winter vacation package?
Most packages combine round-trip flights and hotel accommodation. All-inclusive packages may also include meals, drinks, resort activities and airport transfers, but inclusions vary, so review the package details before booking.
What is the cheapest month for a winter vacation?
January after the holiday rush and parts of early December can offer better value. Prices are usually highest over Christmas, New Year, family day weekends and provincial March break periods.
How can I find the best winter vacation deal?
Compare several destinations, keep your departure dates flexible and check nearby airports when practical. Booking early gives you more choice, while last-minute deals can work well if your dates and destination are flexible.