Boston Vacation Deals

One of the oldest cities in the United States, Boston dates back to 1630 and was the site of many key battles during the American Revolution. Today, the city is home to more than 6 million people and is known for its quintessential Irish pubs, fanatical Boston Red sox fans and a relaxed, small-town vibe. 

Boston has 21 neighborhoods. These include South Boston, popular with young professionals and families; trendy Jamaica Plain, which was gentrified in the early 2000s; wealthy Beacon Hill; and upscale Back Bay, where the city’s iconic brownstone buildings reign supreme. Nearby Fenway is home to Fenway Park, home of the Red Sox baseball team. The more modern Financial District, dense with skyscrapers, is where you’ll find the New England Aquarium. Make time to stroll through the Boston Common in the downtown area. It is the United States' oldest city park, dating from 1634. Take a ride on an iconic swan boat, paddle in the Frog Pond, or see the final resting places of revolutionary soldiers.

With its European-style street pattern, Boston can be a challenge for the uninitiated to navigate. The grid system typical of many American cities doesn’t exist here, but first-time visitors often enjoy getting lost on its narrow, winding streets. From the Boston Common meander through history along the famous Freedom Trail. This 2.5-mile (4-kilometer) course takes you past more than a dozen sites significant to the American Revolution, including Paul Revere House and the USS Constitution Museum. The trail brings you to Faneuil Hall, a marketplace studded with shops, eateries and galleries. Street performers are ever-present here and add to the rowdy atmosphere. 

Boston’s cuisine is eclectic, revealing the influence of the many ethnic groups that moved to the city in the early 1900s. East Boston in particular was a magnet for immigrants from Italy, Guatemala, El Salvador and Brazil. You’ll find plates of rich Italian spaghetti and the popular pupusas, tortillas stuffed with meat and beans. 

Despite the city’s twisting streets, Boston is relatively compact and easy to explore on foot. For longer journeys, take a bus or the subway, affectionately nicknamed “The T.” Boston’s public transport system is one of the best in the country.

For more details on interesting local attractions and activities, check out our things to do in Boston page.

Best time to visit Boston

Summer is a popular time in Boston, as tourists arrive to trek the Freedom Trail and relax in Harvard Square. Hotels are crowded and can be pricey. If cold weather doesn't bother you, try visiting from January to March, especially on the weekends when the city is less congested. Also keep in mind that if you are coming to Boston for graduation (usually mid-May to early June), you'll need to book early and be prepared to pay top dollar.

Peak Season:Summer is the most popular time to visit—which means higher hotel rates and crowded sights. It’s also the best time to enjoy Boston’s outdoor attractions like the Freedom Trail and Boston Common.

Value Season:Winter, especially January to March, can be very cold but also very beautiful. This is a great time to explore the amazing museums, hear the famed Boston Symphony, and dine at the city's many wonderful restaurants.

Accommodation in Boston

Looking to lose yourself in Massachusetts' exciting state capital? Expedia presently lists 282 accommodation options in Boston, so it won't be hard finding a fantastic base for your stay.

Boston's more up-market accommodation options such as the Mandarin Oriental Boston, at 776 Boylston St, and the Four Seasons Hotel Boston, at 200 Boylston St are bound to charm the most discerning visitor. Alternatively, if you're after somewhere a bit more economical, you'll find the cheapest deals at the Beacon Hill Hotel & Bistro, at 25 Charles Street, or the Harvard Square Hotel, at 110 Mount Auburn Street.

No journey to Boston would be complete without a visit to Faneuil Hall Marketplace. If you'd prefer to stay in the vicinity, The Ritz-Carlton, Boston and the Fifteen Beacon are both worth checking out.

Popular Activities in Boston

When we reminisce over our travels, we remember experiences rather than our fancy hotel room and the view of the pool. Are you ready to start creating some new travel memories?

The really awesome news is that Boston boasts heaps of things to do. Here's a selection of our picks:

• Boston's North End History Tour
• Back Bay Wine Tour with Food & Drink Tastings
• Freedom Trail History & Architecture Walking Tour
• After Hours Brewery Tour
• Boston CityPASS: 4 Must-See Museums & Attractions
• City Highlights Guided Bicycle Tour

For a comprehensive range of activities, take a look at our Boston things to do page.

*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.