The Best Airbnbs in Boston, Massachusetts

A stay in a neighborhood Airbnb in Boston will give you a better feel for this historic city
A stay in a neighborhood Airbnb in Boston will give you a better feel for this historic city | © Sean Pavone / Alamy Stock Photo
Photo of Gethin Morgan
Junior Picture Researcher26 October 2020

Boston is a city of distinct neighborhoods, from historic Charlestown to the trendy South End, each with enough personality and history to fill its own guidebook. Whether you’re taking in the city’s historic sights and lively nights or visiting a local college, these Airbnb rentals in Boston allow you to immerse yourself in the city.

Remodeled house with yard and parking in Brookline

Short-term Rental
Map View
Remodeled house with yard and parking in Brookline. This property is the ideal base for families looking to explore Boston
Courtesy of Alex / Airbnb

This completely remodeled five-bedroom house is in a beautiful, leafy neighborhood outside Brookline Village. Sunlight streams into the living room – complete with a fireplace and piano – through large windows and the French doors of a cozy sunroom. The new kitchen gleams in white, black, steel and red, while the en-suite main bath sparkles with patterned floor tiles and a walk-in shower. The third floor has another en-suite bedroom. Between the toy-stocked kids’ room, the large yard and patio and the park-packed streets nearby, families will love this Airbnb. It’s also fairly close to the Longwood medical area and a number of colleges, not to mention two different branches of the Green Line and dozens of restaurants and shops.

Luxurious home in Boston's historic Charlestown

Guesthouse, Short-term Rental
Map View
Luxurious Home in Boston's Historic Charlestown, Boston
Courtesy of Katherine And Dan / Airbnb

Boston’s oldest neighborhood boasts some of the nicest properties in the entire city, such as this townhouse dating back to 1880. The perfect blend of modern living in a historic space, this house hasn’t lost an ounce of charm despite its luxurious makeover, which includes a 65-inch curved TV, memory foam mattress and brand-new kitchen fitted with beautiful copper finishes. When you’re not enjoying the cosy furnishings, the USS Constitution Museum, Boston Harbor and Bunker Hill Monument are all a stone’s throw away.

About this place:

Traditional, Historic, Modern, Great Location, Family Friendly, Affordable luxury, City

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  • Stunning South End one-bedroom with private roof deck

    Apartment, Short-term Rental
    Map View
    Stunning South End 1BR - private roofdeck, Boston
    Courtesy of Matthew / Airbnb

    This modern brownstone apartment in the heart of Boston’s trendy South End is the perfect place to get a unique view of the city, largely thanks to the stunning private roof deck that overlooks the city’s grand skyline. With a spiral staircase inside the flat, you can go straight from the well-furnished one-bed apartment to an intimate, unique city viewpoint, perfect for watching the sun go down and the city lights come on.

    Historic townhouse in center of Boston

    Guesthouse, Short-term Rental
    Map View
    Historic townhouse in center of Boston
    Courtesy of Renee / Airbnb

    You can’t get more central Boston than this charming three-bed townhouse. Tucked behind Faneuil Hall, this is a rare opportunity to find peaceful headquarters amongst the hustle and bustle of the city. Once the workshop of famous Boston furniture makers John and Thomas Seymour, now adapted into a cosy city center home with exposed brick and beautiful wooden beams, this is truly a hidden gem tucked away amidst all of Boston’s rich history, with the Freedom Trail, original Thomas Edison lampposts and much more in its immediate surroundings.

    About this place:

    Cosy, City, Great Location, Traditional, Relaxed, Historic

    Stylish and pet-friendly apartment in Cambridge

    Map View
    Live, work and stay in Cambridge, Boston
    Courtesy of Kia / Airbnb

    If you’re looking to stay in Boston a little longer, then this stylish one-bed apartment is perfect. Situated in a complex that is equipped with a fitness center, billiards lounge, business center and mailroom, this place has all your day-to-day needs covered, so you can commit to a longer stay and truly become an honorary Bostonian. And good news if you have a furry companion joining you, since this building is not just pet-friendly; it also has its own pet bath and spa.

    About this place:

    Modern, Great Location, City, Stylish, Relaxed, Sporty, Business

    This is an updated version of an article originally written by Jon Gorey.

    These recommendations were updated on October 26, 2020 to keep your travel plans fresh.