Boston is brimming with history, thanks to its 1600s roots that make it one of America’s oldest cities. This is evident in the intricate brick structures and lavishly large homes, which now often serve as Airbnbs. Each neighborhood is unique, with some being a serious step back in time. Boutique shopping, artisan eateries, lovely fall foliage and coastal access reside within the city, so there’s always something to do. Staying in an Airbnb is a fantastic way to sink into the local culture and seriously awesome digs, and these are our favorite picks.
Sunny Private Studio Apartment
Want to stay in one of those iconic Victorian homes in Jamaica Plain, that most dream about just taking a peek inside of? This is your opportunity. A full apartment within the home offers ample privacy, and touches of antique aesthetics like a claw foot tub, wood flooring and thick statement trim throughout. All the little extras take the third-floor apartment to “gem” status, such as the private entrance through the garden, and the locally baked treats left especially for you in the kitchen. For the most part, chemical-free cleaning products are used to get everything sparkling.
The Boiler Room
For your upcoming trip to Boston, book this rental unit that’s a private suite with its own private entrance. The suite has a queen-size bed and is clean and nicely decorated. The location of the suite is within a five-minute walk to the Ashmont T. Station (Red Line), which will take you downtown. It’s a creatively inspired room on the garden level and comes with a private bathroom and kitchenette. If you stay for seven or more days, you can use the washer and dryer. There are additional rooms that you can rent for overnight stays on this same property.
219 on the Ocean with Private Bath
Budget-minded travelers should consider this private room in a Boston home in Savin Hill. The rental includes a private room that is connected to a full, private bathroom. The bed in the private room is a full/double-size bed. Your space overlooks the Malibu and Savin Hill Beaches. It is easy to get here from downtown and the airport. It’s quiet and beautiful, offering you plenty of privacy and solitude. Solo adventurers, business travelers, and healthcare workers love staying here, but it is comfortable for two people also.
Brand-New One-Bedroom on Charles Street
You and two other guests can rent this Boston Airbnb and enjoy a great location in Beacon Hill. It has a spacious living room, kitchen with high-end appliances, lovely bathroom, and central air conditioning. It is a basement apartment in the lower level of a four-story brownstone home on Charles Street. With this vacation rental, you’ll have a 55-inch TV, Wi-Fi, Keurig coffeemaker, and a common washer and dryer to use for laundry. The closest subway stop is at the end of the block, which is a two-minute walk away.
Naturally Lit, Modern Loft in Heart of Downtown
Four people can book this Airbnb in Boston and have one bedroom and one bathroom in the heart of downtown. The loft has an open floor plan and lots of natural light. It is decorated with designer touches and offers a modern kitchen, fast Wi-Fi, and high-end toiletries. For sleeping, there is a king-size bed in the bedroom and a full-size sofa bed in the living room. You can access all subway lines and a grocery store near the apartment, which is in a secure building with elevators.
City Escape in Back Bay with Parking
Travelers to Boston will enjoy staying at this studio condo because of the great location and easy access to everything in the city. It is a place to stay for up to four people and a little sanctuary away from the busy city life. The space has a Victorian-era feel with modern updates for a charming and unique vibe. The bedroom has two queen-size beds for you and your travel companions. It also has a window A/C unit to keep you cool in the summer and all the amenities you need for either a weekend getaway or an extended stay.
Historic JP Brownstone
Anywhere with historic roots in Boston is likely going to be a win. You can almost see the atmosphere over 100 years ago in this striking Brownstone building that blends perfectly into Boston’s other old gems. At 1,200 square feet, the condominium is spacious and absolutely charming. A beautiful wood banister staircase, wood flooring, a bay window along with countless other windows to let light in and a floor-to-ceiling brick fireplace creates a cozy atmosphere. Boston is easily accessible from this Jamaica Plain location, but you have the benefit of peace and quiet with plenty of trees and grassy play areas.
Room at the Top - South End Brownstone Penthouse
This Boston Airbnb rental is a private room in a loft that works well for one or two guests. The bedroom has a double-size bed, and you’ll also have a flat-screen TV and access to a kitchen. The room is part of the host’s apartment on the top floor of an 1850s brownstone building. There is no elevator to access the space. However, you’ll love the Boston skyline view from your room’s windows. People often stay here when they are attending conventions at the Hynes Auditorium, which is a 15-minute walk away.
Two-Bedroom Spacious Yacht
Experience Boston from the water with an Airbnb stay on this yacht. Known as “Carpe Diem II,” the yacht accommodates up to five guests and has queen-size beds in each of the two bedrooms, plus a sofa bed in the living room. It’s fun to stay here and enjoy 360-degree views of the marina and harbor. The interior offers a smart TV, comfortable seating, galley kitchen, and cooking basics. The location of the yacht is in the historic Charlestown Navy Yard, which is just steps from the Freedom Trail, downtown, and the North End.
Historic House, Modernized
Large groups of up to 12 people can stay at this Boston Airbnb that has five bedrooms and two bathrooms. The home is in a safe neighborhood that is just 200 yards from Brighton Center and five miles from downtown Boston. It dates back to 1860 and has been divided into apartments and condos. This is a great place to stay to experience the history of Boston, but be prepared for steep stairs and small room sizes. Guests staying here will have a large yard, outside BBQ, patio dining, game room, porch, and off-street parking for two cars.
The Cosmopolitan
The Cosmopolitan is a popular Airbnb rental that has two bedroom and one bathroom for Boston travelers. It’s a stylish and family-friendly place to stay with a large, eat-in kitchen and free street parking. You’ll be in the Hyde Park neighborhood, which is a 30-minute drive to downtown Boston. The home comes with free Wi-Fi and Netflix, as well as access to a shared washer and dryer and a shared patio and backyard. Let the host know if you are traveling with a baby and need a travel crib during your stay.
Stylish Stay with Queen-Size Bed & Heated Floors
Simplicity might be what you are looking for when planning on spending most of the time out and about amongst the city. Fenway is a short distance away from this rental. With a studio layout, things are quite spacious, but everything you need for comfort and convenience resides within.
Modern 3-Bedroom Home Near BCEC
Need something a little larger, that would suit an entire family? Three lovely bedrooms and one and a half baths can be found inside this traditional Boston home. We love that the decor feels very much like home, but still trendy and clean-cut enough to feel like a true vacation getaway.
Cozy Studio Apartment in Jamaica Plain
This studio apartment for rent is on the second floor of a building and is centrally located in Jamaica Plain. It is a two-minute walk to the Orange Line Stony Brook subway train station from the apartment. Therefore, you can get to downtown Boston within 10 minutes by public transportation. Two people can stay here and use the queen-size bed and bathroom. It also comes with access to a full kitchen, Wi-Fi, and cable TV. You’ll have your own entrance to access the unit, and the Sam Adams Brewery is a five-minute walk away.
45-Foot Yacht in Boston Harbor
A unique way to experience Boston is to book a yacht for your overnight stay in the city This private yacht is available to rent on Airbnb and is docked at Boston Harbor. The boat remains docked at all times and has two queen staterooms, each with a bathroom and shower. There is a galley kitchen here with a full refrigerator and dinnerware. You can also grill out on the community BBQ on the docks. The boat rental is within walking distance of the USS Constitution and Bunker Hill Monument, within a gated and secure community with evening security during the summer.
