Flight + Hotel
Flights
Cars
Cruises
Smart Cancun
44 star hotel
- 7 nights
- Smart Room
- Flights incl.
FromCA $1,051/ person · incl taxes & fees
Winter Vacation Deals
Escape the cold with winter vacation packages to sunny beaches, all-inclusive resorts and warm destinations.
Coming soon
Flight + HotelFlightsCarsCruises
- Great rates. Clear prices.
- Book with confidence
- Real people. Real support.
Earn
on every booking
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
Reserva Real By Harper
4.54.5 star hotel
- 7 nights
- Run Of The House
- Flights incl.
FromCA $1,089/ person · incl taxes & fees
The Fives Downtown Hotel Residences
4.54.5 star hotel
- 7 nights
- Deluxe Room
- Flights incl.
FromCA $1,218/ person · incl taxes & fees
Vik Hotel Arena Blanca
44 star hotel- 7 nights
- Room Gardenview
- Flights incl.
FromCA $1,228/ person · incl taxes & fees
Krystal Puerto Vallarta
44 star hotel- 7 nights
- Deluxe Mountain View
- Flights incl.
FromCA $1,239/ person · incl taxes & fees
Marien Puerto Plata Hotel
44 star hotel- 7 nights
- Deluxe Gardenview Double
- Flights incl.
FromCA $1,252/ person · incl taxes & fees
Bluebay Grand Esmeralda Riviera Maya
44 star hotel- 7 nights
- Promo Room
- Flights incl.
FromCA $1,257/ person · incl taxes & fees
Hm Alma De Bayahibe Hotel
44 star hotel- 7 nights
- Room
- Flights incl.
FromCA $1,271/ person · incl taxes & fees
Catalonia Yucatan Beach
44 star hotel- 7 nights
- Comfort Room
- Flights incl.
FromCA $1,277/ person · incl taxes & fees
Transparent pricing
Book with confidence
Real people. Real support.
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.