Airbnb Boston: 15 Exemplary Listings to Check Out

Boston vacation rentals are seeing a rise in demand. With so many landmarks a stone’s throw away from the city center, visitors to this historic city can explore anything from Fenway Park to the Paul Revere house. The bay and its Atlantic waters shape the Boston seafood-based food scene, while also keeping the city center smaller and making the area easy to navigate.

Boston is among the oldest cities in the United States. Rivals may try and make New York City their sweetest brother, but its compact size makes it’s quality even better.

No matter where you are it is easy to reach the rest of Boston via foot or the Boston subway system. It has many activities despite its modest scale. Whatever reason you visit Boston, there is something for everyone.

1. Luxurious Home in Boston’s Historic Charlestown

One of the most beautiful Airbnbs in Boston that you can find, the home feels peaceful and somewhat secluded, like you’d want it to. In Charlestown, Boston’s newest neighborhood, you can really discover Boston’s history by visiting several museums and the historic US Constitution Warship.

The best part about this apartment is that it can accommodate 4 people. It can be accomplished thanks to a queen-size mattress in the bedroom and a pull out couch in the living area that works perfectly for a young family traveling together.

Host Takeaway: This property’s sleek, modern design still feels homey against its historic surroundings. Featured in Boston Design Guide, this home really delivers on all the most important amenities in the most stylish way and provides easy access to local landmarks on top of that.

2. Beacon Hill Townhouse

The Beacon Hill townhouse of the 19th century offers the ideal place for a couple wanting to be in the center of the village. Amazing Boston Airbnbs are located in historic Beacon Hill on a walkable street, meaning Boston Public Garden and Freedom Trail are just a short walk away.

This 4-bedroom house is the perfect place for you to start your first trip to Beantown. The holiday home features historical elements from the 1800s which were first renovated by the owners and was then completely refurbished in 2012 by bringing modern amenities into the house. It has a comfy sofa, a fireplace, and original artwork.

Host Takeaway: Boston townhouses are an architectural staple in the city and this one, built in 1850, really plays into the historic charm by being furnished with antiques. If you’re looking to attract history buffs, this is a wonderful example to follow.

3. Modern South End Condo

Comfortable stay in a cute, modern home located in the desirable south end. Steps away from parks, cafes, trendy restaurants, bars, and Whole Foods.

Includes a fully functional kitchen, cozy living room with fireplace, an outdoor patio with firepit, and bathroom with a rain showerhead. It’s the perfect little setup for 2-3 people.

Quick access to major neighborhoods including a short walk/drive to Back Bay, and Seaport. Bus and silver lines are close by. Enjoy the city and come home to unwind in a quiet oasis.

Host Takeaway: In contrast to the previous listing, this property has a classic exterior with an ultra-clean modern interior. It’s super functional and a great base of operations while exploring the city.

4. Sunny Artist Loft In Historic Brownstone

Sunny artist loft in a Victorian brownstone, located 3 miles from downtown Boston, in Roxbury. The one-bedroom apartment is located on the third floor of a walk-up and features an open, airy floor plan with exposed brick. Perfect for a relaxing Boston getaway and easy access to most attractions.

Easy access to public transportation, major highways, airport, hospitals, convention centers, museums, colleges, and universities… The apartment features a large spa bathroom with a soaking tub and rain shower. The hosts also offer a fully stocked kitchen with a gas range, farm sink, coffee maker, and blender.

Host Takeaway: Another classic brownstone, this property plays up its Victorian-era charm with exposed brick and distressed features while remaining sunny and comfy. It serves as a great example of a property that embodies the look and feel of the city it’s in for out-of-towners.

5. Newly Renovated Apartment with Ocean View

Come relax in a newly renovated apartment with an ocean view that sleeps up to 6 people (2 separate bedrooms & sofa bed in the living room. With a new kitchen & bathroom with top-line appliances, the property is within walking distance of the beach. TVs in every room will keep your friends/kids entertained and a desk – with a standing option – is ready if the office calls.

The second floor is filled with light and ocean views. You will also have the use of the downstairs patio and grill.

Host Takeaway: You really can’t go wrong with an ocean view and some creature comforts. This property really said “Location, location, location” and nailed it. While the interior of the apartment is quite basic, it makes up for it in spades with the patio and sea view.

6. Charming Historic Bay Village Apartment

Relax in the city’s center in this charming one-bedroom apartment located in Bay Village. This historic brownstone rowhouse, which is off of a tiny cobblestone street, provides an unexpected sense of peace while still being close to the city’s top dining and entertainment options.

The apartment’s fantastic location has a beautiful view of the city and is on the second story, accessible by two flights of steps. Fast internet access makes it convenient for both traveling and working remotely.

The other two units of the building share the common roof deck, which has a stunning view of the skyline of Boston.

Host Takeaway: A truly charming old brownstone rowhouse with a cozy interior, the space is functional and comfortable. The main draw, however, is the roof deck with a spectacular view of Boston’s city skyline. It’s the kind of feature that really sets this property above the rest.

7. Lofty South End Penthouse

Take advantage of all Boston has to offer with this lofty penthouse. You’re guaranteed to adore the space whether you’re traveling for work or play!

This loft is within walking distance of many bus lines that will take you directly to South Station, Back Bay, or Copley. It also has quick wifi and easy street parking. It offers a stunning bathroom with a heated marble floor and an amazing skylight view of the city! Includes two very comfy queen-size beds as well.

The apartment is located on the third floor of a Boston Brownstone from the late 19th century that has no elevator.

Host Takeaway: Exceptional design and comfort come together in this property. The slight industrial feel of the living space contrasted with the sleek kitchen creates the perfect balance. Did we mention the heated marble floor in the bathroom with the incredible view through the skylight in the shower?

8. Luxury Rental Close to Universities

This unit is opulent, fully equipped, ideal for groups of friends and family, and conveniently close to Logan International Airport in the lovely West Revere neighborhood. Additionally, the property is approximately 20 minutes from Downtown Boston and close to major universities including Harvard, MIT, Boston University, and Suffolk.

Stainless steel equipment and modern furniture are used to adorn this spacious and opulent flat. The home has a really good deck and a backyard that is meticulously maintained. The home has two parking spaces and is completely enclosed for privacy.

Host Takeaway: Further out from the Boston city center, this property is ideal for families and bigger groups that need more space and maybe have a pet that needs room to stretch their legs. It’s comfortable, functional, and capitalizes on Boston’s many attractions without being smack in the middle of it.

9. Charming Studio in Little Italy

Stay in a charming, historic studio apartment in Boston’s exclusive North End. Hanover Street, the Waterfront, and the Freedom Trail are all easily accessible from this location, which is beneath the Old North Church and close to Copp’s Hill. Any trip around Boston is simple from this spot.

Additionally, the resort is adjacent to some of Boston’s most well-known sights, including TD Garden, Quincy Market, Faneuil Hall, and the Aquarium (home of the Bruins and Celtics).

Host Takeaway: This studio is a great example of how you can repurpose an otherwise underutilized space. It feels like a basement apartment that has been renovated while maintaining the historical charm with its exposed beams and brick walls.

10. Charming Apartment in Chelsea

The Chelsea House, an apartment on a narrow one-way street, was constructed in 1900. It is a three-family brick structure that is quiet and well-kept, and it is on the third level. The sloping loft ceilings, exposed brick, and hardwood floors provide a beautiful, warm, and intimate ambiance.

On the other side of the bay, in the North of Boston, is the conveniently positioned neighborhood of Chelsea. Although it’s not exactly in Boston proper, TD Garden, Encore Casino, Seaport, and Downtown Boston are nonetheless fairly nearby.

Host Takeaway: Charming, warm, and cozy really hit the nail on the head here. This apartment amps up the home-away-from-home comfort while still having its own unique charm. Its location in a lesser-known neighborhood to travelers just outside of Boston proper is also a bonus for those looking for less intense surroundings.

11. Astonishing 1 Bed in Boston’s South End

The picturesque South End neighborhood, with its brownstones, brick sidewalks, and tree-lined streets, is home to this tastefully furnished and freshly restored apartment. It contains a queen memory foam pullout sofa and a queen memory foam bed. Up to four guests can stay there. This intriguing and spotless apartment also has brand-new furnishings and accessories.

It is just minutes away from Downtown, Boston Common, Back Bay Newbury Street, Copley & Prudential Malls, Theater District, Beacon Hill, and the Charles River.

Host Takeaway: Another exceptional location, this property is situated close to some of the best dining spots in town. Super central it’s also a stone’s throw away from multiple attractions.

12. Casa Paradiso in Cambridge

This bright, expertly decorated top-floor apartment in a Cambridge property has a Havana vibe. This vacation rental has a walking score of 93 and is located in a vibrant area with fantastic restaurants, coffee shops, craft brew pubs, and supermarkets.

A lovely garden is located in the backyard and is shared with the other flats. Views of it from the kitchen, as well as views of Prudential and John Hancock, are extremely tranquil to take in while sipping coffee.

Host Takeaway: Exceptionally designed, this apartment oozes charm. While going for a Havan theme in Boston might seem like an unusual choice, it’s executed tastefully. If you want to go for a theme in your space, why not? As long as it remains functional and doesn’t lean towards tacky it could be a real draw for people.

13. Downtown Brick + Beam Loft

The Boston Common is only a 3-minute walk from this centrally situated two-bedroom, one-bathroom apartment with in-unit laundry. Light is abundant thanks to the large windows. The kitchen is well equipped with everything you need to prepare a simple dinner.

Mass General Hospital is ten minutes away by vehicle or public transportation, and it takes twenty minutes to walk there.

Host Takeaway: Bright, comfy, and central, this space is ideal for a small group or a solo traveler. Another space that capitalizes on the exposed brick and architectural features, this property are neutral enough to please most while still holding onto some personality. Where you can, use the building’s existing features to your advantage.

14. Private Roof Deck in South Boston

Located in the center of South Boston, this master suite is flooded with natural light and offers stunning views of the city. Restaurants and stores on West Broadway are a 5-minute walk away. The walking time to the Broadway T stop is about 15 minutes.

This private space is located in the host’s house. You will have exclusive use of the entire third floor, as well as the common kitchen and laundry room.  The roof deck, where you may have your morning coffee or tea or a late-night beverage with a fantastic panoramic view of the city, is the nicest feature.

Host Takeaway: Another exceptional roof deck, this example really ups the comfort and style. Don’t simply rely on the view but instead try to style the space in a way that either frames or compliments the view.

15. City Sanctuary with Ocean View and Terrace Garden

In addition to having a terrace with breathtaking views of the ocean, garden, and JKF library, this spacious, private studio is located directly across the street from the well-known historic park Dorchester Heights. Additionally, the conference center, airport, downtown, charter buses, and trains are nearby. Excellent neighborhood stores and hangouts are accessible on foot.

It is a quick 2-block walk to the beach from its location on Historic Thomas Park, which is across the street from a lovely park and close to the Seaport and local eateries and pubs.

Host Takeaway: Another one for the history buffs. This listing includes the detail that it’s located across the street from historic Dorchester Heights park where George Washington fought the final battle of the revolution. Try to include historical relevance if your property has some trivia because it’s a great tidbit for guests to slip into conversations after their stay.

When is the best time for a vacation rental business in Boston?

Boston’s Autumn paints the city in traditional New England colors over a chilly summer and a less cold winter. Spring offers similar warm weather although the thawing in January and the milder rainfall can make things muddy.

April has an annual marathon weekend, formally an annual state holiday called Patriots’ Day. Thousands of fans attend the third week of every month.

In winter low temperatures rarely exceed below freezing and you’ll enjoy a great off-season rental opportunity.

Conclusion

There you have it. 15 inspiring Airbnbs in Boston that you can refer to when setting up your own vacation rental in the city.

Starting your own vacation rental business can be daunting, but with the right tools and support, you can see your own Boston property paying off in spades in no time.

Software like iGMS will help automate the check-in and guest reviews, as well as generate direct bookings via its website builder.

In addition, it can also help with tasks like:

• Managing several accounts and listings on the leading vacation rental platforms via a single interface
• Synchronizing bookings across multiple platforms to reduce the risk of double-bookings
• Receiving payouts and creating invoices by connecting your Stripe account to iGMS
• Enticing guests to leave reviews by automatically sending reminders
• Managing direct bookings using a direct booking management toolkit
• Creating key performance reports within minutes
• Adjusting your room rates regularly through integrations with dynamic pricing software