The Best Airbnbs and Vacation Rentals in Boston, Massachusetts

Booking a vacation rental in Boston will give you a better feel for this historic city
Booking a vacation rental in Boston will give you a better feel for this historic city | © Sean Pavone / Alamy Stock Photo
Nick Dauk

As one of the oldest cities in America, Boston means business. From the history-rich Freedom Trail and Fenway Park to the shop-studded Faneuil Hall Marketplace, nearly every avenue in the capital of Massachusetts holds a relic of the past, a trademark of the present and a glimpse of the future. Drop your bags at one of these spectacular vacation homes in Beantown – bookable with Culture Trip.

1. Cool crashpads for couples near Boston Common

Short-term Rental

Sonder - Hancock Suites_5c074c38
Courtesy of Sonder – Hancock Suites / Expedia

Street carts and people-watching make Boston Common the ultimate backyard. Inside, these cozy, characterful one-bedroom suites with bright contemporary furnishings sleep two people, perfect for couples. You can instantly immerse yourself in the city’s history by venturing through the Boston Massacre Site and Boston’s Old City Hall before grabbing a lobster roll from Wicked Lobsta in Faneuil Hall Marketplace. Also, the 18th-century Massachusetts State House is a short stroll away.

2. Sleek suites near Fenway Park

Short-term Rental

Sonder - Pierce Boston_907a2a89
Courtesy of Sonder – Pierce Boston / Expedia

There’s a Green Monster (the name given to the 37ft-high (11m) wall of Fenway Park, home to the Boston Red Sox) lurking near these suites, and the five-minute walk to the famous baseball stadium is a grand slam even if you’re not a fan of America’s national pastime. You can also take a stroll down the monument-filled greenway of Commonwealth Avenue Mall before exploring the nearby brownstone-lined Newbury Street, followed by the upscale department stores at the Prudential Center. Back at base, studios and suites sleep between two and six people, and all come with snappy modern furnishings and scenery-spying views through floor-to-ceiling windows that’ll make you feel like you’ve hit a home run.

3. Hip hangouts near Chinatown

Short-term Rental

Global Luxury Suites Downtown Boston_d665469a
Courtesy of Global Luxury Suites Downtown Boston / Expedia

See a different side of Boston on the outskirts of downtown at these pet-friendly luxury apartments. Splurge on the premium suite with city vistas to get a bird’s-eye view of Chinatown and the Boston Theater District. When you’re not hanging out on the balcony of your two-bedroom abode, which sleeps five total, we suggest getting acquainted with the Cantonese lobster and other Far East dishes around the Chinatown Gate.

4. West End digs for ice-hockey fans

Short-term Rental

Global Luxury Suites at West End_dd384c58
Courtesy of Global Luxury Suites at West End / Expedia

Trade harbor hangouts for riverside relaxation in Boston’s West End. These luxurious one- and two-bedroom apartments sleep three to five guests who will relish their mix of convenience and comfort. A hot cup of coffee and a cool Boston breeze on the balcony are perfect for post-morning workouts in the 24-hour gym. The Charles/MGH station just outside will take you to Harvard for a couple of bucks, but for those who are more sporty than scholarly, the 10-minute walk to the TD Garden arena has a few Bruins, beers and blue-line battles waiting for you.

5. Remodeled house with a yard and parking in Brookline

Short-term Rental

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 French doors that lead to the cozy sunroom. The new kitchen gleams in white, black, steel and red, while the bathroom in the primary bedroom sparkles with patterned floor tiles and a walk-in shower. The third floor has another ensuite 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.

6. Luxurious home in Boston’s historic Charlestown

Guesthouse, Short-term Rental

Boston’s oldest neighborhood has some of the nicest properties in the entire city, such as this townhouse dating back to 1880. With 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 an HDTV, a memory foam mattress and a brand-new kitchen fitted with beautiful copper finishes. When you’re not enjoying the cozy furnishings, the USS Constitution Museum, Boston Harbor and Bunker Hill Monument are all a stone’s throw away.

7. Stunning South End one-bedroom with private roof deck

Apartment, Short-term Rental

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 overlooking the grand skyline. Via the spiral staircase inside, you can go straight from the well-furnished one-bedroom apartment to an intimate, unique city viewpoint, perfect for watching the sun go down and the city lights come on.

8. Stylish and pet-friendly apartment in Cambridge


If you’re looking to stay in Boston a little longer, then this stylish one-bedroom 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 an extended stay and truly become an honorary Bostonian. And if you have a furry companion joining you, this building is not only pet-friendly, but it also has a pet bath and spa.

This is an updated version of an article originally written by Jon Gorey. Gethin Morgan contributed additional reporting to this article.

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