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Flexible Companies That Are Willing To Help You Pay For Your Vacation

More Americans are taking vacations as travel restrictions have been loosened and long-delayed trips are rescheduled. According to a recent survey, 90% of people plan to travel this summer, with nearly half taking two or more weeks off!

According to studies, Americans take an average of 54 percent of their vacation days. Some employers provide stipends, discounts, and reimbursements to employees who take vacations in order to encourage them to spend more time resting and relaxing.

The job market today is tough for employers! Given the fierce competition for top talent, many businesses are incorporating creative benefits into their perks package.

Check out the companies listed below for day-to-day flexibility and assistance in planning a vacation.


TripAdvisor is a travel website that allows users to book flights, hotels, and vacation rentals. Depending on how long employees have been with the company, they are eligible for travel reimbursements of $300 or more. Discounts on packages booked through the site are also available to workers.


Airbnb was founded in 2008 as an online hospitality marketplace for connecting hosts and travelers. Airbnb lists homes, rooms for rent, villas, boutique hotels, and other accommodations.

Thousands of people have benefited from its 2 million global listings. Annual travel and expense credits are given to employees.


Evernote is a multi-purpose app that lets you take, organize, and share notes all in one place. Each note can contain links, tables, audio messages, and more. Employees are given unlimited vacation days and a yearly vacation stipend of $1,500.


Basecamp, which was founded in 1999, is the name of a popular project management tool. The distributed company employs 50 people in 32 locations. Employees who have worked for the company for one year or more can choose from 16 different paid vacation packages each year, according to Business Insider. Each of these trips is worth $4,500-$5,000.

Motley Fool

Through its business and investing advice, the Motley Fool aims to make its readership wiser, happier, and wealthier. The company also has a program, in which one employee’s name is drawn from a hat every month and awarded money toward a two-week vacation. The lucky winner must take the trip before the next monthly meeting and is asked to keep in touch with no one while on the road to ensure maximum relaxation.


Expedia has served customers in over 60 countries as a well-known travel booking site. Users can book flights, hotels, rental cars, cruises, and even activities through the website. Employees receive a travel reimbursement ranging from $250 to $750, depending on their length of service. They also get discounts on the site’s retail and travel package.

Airlines United

United Airlines, headquartered in Chicago, Illinois, was founded in 1926 and is one of the world’s largest airlines, with 4,500 daily flights to more than 355 airports on five continents. Employees get unlimited standby time and discounted ticket prices on United Airlines flights worldwide.


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