2,051 Boston Holiday Rentals

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Compare Boston holiday rentals from 15 rental sites including Booking.com, HomeAway, TripAdvisor and more, ranging from $25 to $987654 a night.

Information about Boston

About Boston

Best identified with the iconic Boston Tea Party, Boston Marathon, Harvard, and the Red Sox, Boston, Massachusetts is one of America’s most populous states. It is also site of the country’s first subway system and home to an astounding number of Dunkin' Donuts. As you land at Logan International Airport, one look at Boston’s skyline gets you excited to explore this ‘City on a Hill.’

Boston Neighborhoods

Boston is made up of many neighborhoods - Tremont, Shawmut and Washington streets in the South End have a number of restaurants and retail stores scattered all over. South End is also home to the famous Boston Ballet and the Boston Center for the Arts (BCA).

Back Bay is dotted with charming Victorian houses. It also houses two of the tallest buildings— the Prudential Center and the John Hancock Tower. The Old Hancock Building is easily spotted for its aerial weather beacon illuminated with red and blue lights. The famous Boston Public Library is also part of this neighborhood.

Downtown Boston holds the Financial District and the Government Center. Emerald Necklace is a group of parks that were constructed to encircle Boston. The country’s oldest national park - Boston Common – is also a part of this. Jamaica Pond and the Franklin Zoo are other attractions that contribute to this design. The Hatch Shell located along the banks of the Charles River is a popular venue for concerts and is adjacent to Esplanade Park.

Things to Do in Boston

The Freedom Trail is one of Boston’s iconic activities – and you can do it the fun way – a costumed tour! Some key highlights of the Revolutionary War are the home of Paul Revere, Old North Church and the Old State House museum. Follow our weekend getaway guide to plan the perfect trip.

If you’re in the mood for some theater, head to the Theater District to catch a show at the Citi Performing Arts Center or the Orpheum Theatre. If you’re around at the right time, you can attend one of the city’s many annual events - First Night on New Year's Eve, the Boston Arts Festival and the Harborfest activities of Fourth of July. The Charles River fireworks with the Boston Pops Orchestra are a great way to celebrate this holiday!

If you time it well, you may be able to catch a game with any of Boston’s four major professional sports leagues – Red Sox, Celtics, Patriots and Bruins. Even if they’re on the road, a trip to Fenway Park could still win you a beer at one of its famous bars.

Make a trip to the Boston Public Library to see its many murals or the Institute of Contemporary Art in South Boston for its remarkable architecture, or check out these free events in the city. Walk along the Esplanade to enjoy a view of sailboats on the river or take a trip to the New England Aquarium, and catch a glimpse of the penguins and hermit crabs that call it home. And once you’re done, a great way to unwind is to get on top to the Prudential Building's Skywalk Observatory to get the ultimate 360-view of Boston. If the idea of a drink with a view sounds appealing, head to one of these rooftop bars for a sunset cocktail.

Boston Accommodations

If you’re on a budget Boston vacation, Boston apartment rentals in the Back Bay and Beacon Hill neighborhoods may prove more expensive. You could expand your search for Boston vacation rentals to include the greater Boston area to get more options – homes for rent are available in all parts of the city. If you do decide to look for an apartment for rent in Back Bay, try and get one with a view of the Charles River to get the true Boston experience.

Spring and Fall are the best time to be in Boston – especially if you’re looking to avoid the cold Boston winters!

Day trips from Boston

If you're eager to escape the hustle and bustle of the city for a more tranquil setting, the possibilities are endless in Massachusetts. You can drive a few hours to the charming town of Falmouth and get on the ferry to Martha's Vineyard to spend the day biking, hiking, and enjoying the sea breeze. Or drive out to Dennis on Cape Cod to get a lobster roll at Captain Frosty's before driving along the waterfront. You can leave your car behind if you choose to go to Rockport, where you'll fall in love with the charming scenery and interesting town.

Vacation Rentals in Boston

Find the best Boston vacation rentals with Tripping.com. Choose from 3293 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $987654 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 1438 of homes in Boston offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 107 rentals with pool or jacuzzi, or relax with the family in one of the 981 homes with cable TV.

For all those dog lovers and cat lovers, Boston offers 337 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 15 rental sites in Boston where the top providers in that area are Booking.com, HomeAway, and TripAdvisor. There are 1462 Booking.com rentals, 1123 HomeAway short term rentals and 283 TripAdvisor vacation rentals.