Best winter travel deals

Created date

November 24th, 2015
snowman made of sand
snowman made of sand

As snow starts falling in most parts of the country, who isn’t dreaming of a warm-weather getaway? You can escape to warmer weather this winter for less by following the savvy advice of travel industry insiders.

If you’re retired, you’ve got time on your side. That translates to big savings when it comes to travel.

“Retirees are blessed in that they have more flexibility in their travel dates,” says Dave Dudar, founding chairman of the Convention and Visitors Bureau, Atlanta Airport area. 

Dudar says the cheapest dates for winter travel are Dec. 1–15. Rates increase after that through the New Year, and then fall again until the first week of February.


Choosing the right location can also make a big difference in the cost of a winter vacation. Dudar says current value destinations include Guatemala and Mexico, where he says food and hotels are typically half the price of what you’d pay in the Caribbean or Hawaii. He also recommends Nicaragua and Colombia.

“Though the biggest bargains there are the cities of Bogota and Medellin—trendy and beautiful Cartagena has gotten expensive,” Dudar says.

Lidia Shong of, which provides free online financial services to Baby Boomers, says to consider places where the local currency is devalued against the U.S. dollar so you can get the most bang for your buck.

“For example, I am booking a trip to Brazil during Christmas and got a rental car for less than $100 for the entire week,” she says.

It also pays to book flights at the right time. Paul Moyer of says the best fares are usually available five weeks ahead of time. This is when the airlines typically lower rates to make sure the plane has enough passengers,” he says. “Once they have enough, they start raising rates.”

Home rentals

An increasingly popular alternative to hotel stays is home rentals through sites like and Renting a home rather than a hotel room offers more space and is typically less expensive, so you may be able to afford to stay for longer.

“Vacation rentals are budget-friendly, as they are half the cost and twice the space of a hotel room,” says Maddi Bourgerie of “They come with a ton of cost-saving amenities that would be extremely beneficial for retirees, including full kitchens to cook food and a washer/dryer for laundry.”

Bourgerie says you typically need to book home rentals 90 days in advance. But, she says, if you are flexible, you may be able to score a last-minute deal from homeowners looking to fill open weeks. If you’re seeking peace and quiet more than hustle and bustle, Bourgerie says you may be able to get a good rate on a rental.

“Look for vacation rentals farther away from popular attractions, such as the waterfront, theme parks, and so on,” she says. “The farther you are from tourist attractions, the less you can expect to pay.”