Boston Flight & Hotel: Where To Book The Best Package Deals

by Scott Dylan  |  Published August 3, 2018

One of the oldest cities in the United States, Boston is packed with history as well as contemporary charm. Take a walk down the Freedom Trail and relive the early history of American independence, catch a game at Fenway Park or grab some grub in Boston’s iconic North End neighborhood—there’s plenty to do in the City of Liberty.

Boston (Photo_: Patrick Franzis via Flickr)

There are dozens of travel companies that offer flight and hotel vacation packages to Boston. We researched them all and ranked them according to factors such as price, deals, customer service, flexibility and cancellation policies. Here are our top three picks:


Book at

Expedia is our favorite for booking a vacation package to Boston. Expedia is a top-tier travel company, offering a wide selection of hotels and nearly every flight option to Boston. While you can sometimes find a cheaper flight or hotel on another site, the total package price offered by Expedia will usually be cheaper. Expedia is also our top pick for booking family vacation packages. We researched numerous packages with flights from Chicago, Atlanta and San Francisco and found that a couple could save between $100-$350 on a 3-night stay at a 4-star hotel. Expedia’s cancellation/change policies are pretty flexible if you have a change of plans. Expedia offers free cancellation within 24 hours of your booking, although hotels and airlines may still charge cancellation fees. To avoid this, you can buy Expedia’s Vacation Waiver insurance, which allows you to cancel fee-free up to 24-48 hours before your booking begins.


Book at

Priceline matches Expedia pretty closely in terms of choices, offering a wide selection of hotel and flight options in an intuitive and easy-to-use interface. After checking rates for numerous vacation package deals, we found that Priceline costs a bit more than Expedia, on average. The exception was for stays of one night, where Priceline was generally cheaper than Expedia. On non-discounted deals, Priceline guarantees a full refund on the flight segment of your vacation package if you cancel within 24 hours of your booking, but this policy doesn’t cover JetBlue, Spirit Airlines and Air India.


Book at

JetBlue is a budget carrier that also offers combined flight and hotel booking packages through JetBlue Vacations. They currently offer cheap vacation packages to Boston from New York, Fort Lauderdale, Denver, Chicago, San Francisco and Los Angeles. The downside is that JetBlue Vacations’ offers a more limited selection of hotels than Expedia or Priceline, and, of course, you can only fly via JetBlue. The other disadvantage of booking with JetBlue Vacations is that their cancellation and change policies are much stricter: if you cancel or change a booking 60 days or more before your scheduled departure date you’ll pay a $70 fee, per person. Cancel or change a booking any later than that and you’ll pay $135 per person, not including any fees charged by the hotel. We always recommend checking Expedia and Priceline before you book with JetBlue Vacations as you’ll sometimes pay a lot more on certain trips.