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Airbnb Houseboats
13 Best Airbnb Houseboat Rentals In Boston - Updated 2025

Over 18 million people visit the popular sights of Boston every year. One of the most popular things to do whilst in Boston is to follow The Freedom Trail, a historical 2.5-mile-long (4 km) path through the downtown area. After that, you could take a stroll through the parkland to visit North End (Little Italy). Another popular way to spend time here is to take a boat out into Boston Harbor's waters. If you're a novice, you can consider heading to Boston Sailing Center for a lesson or two. In the evening, head back to your own unique boathouse or yacht and enjoy dinner on the deck whilst watching the sunset over the water. To make this dream a reality we've found the top houseboats, which are sure to guarantee an unforgettable holiday. Start planning your holiday and book one of these best Airbnb houseboat rentals in Boston!
Vrbo
14 Best Vrbo Vacation Rentals In Boston, Massachusetts - Updated 2025

Boston, the capital city of Massachusetts, has an important place in America's history and in the world's education. With a large number of technical jobs available, plenty of museums, cultural events, amazing food options, and a diverse and liberal culture, Boston offers an area of comfortable living. Hunker down for the holidays and catch the Boston Tea Party Anniversary, held every 16th of December. You can also book tickets for concerts and acts at the Berklee Performance Center. Being such a big place, you might get overwhelmed with your stay options while planning the holiday. To help you decide, make sure to take a look at our list of the best Vrbo vacation rentals in Boston, Massachusetts.
Cheap Airbnbs
25 Cheap Airbnbs In Boston, Massachusetts - Updated 2025

The East Coast city of Boston is the capital of Massachusetts. This multi-cultured city is full of history, having been established in the year 1630 and was the scene of several key events of the American Revolution, such as the Boston Massacre and the Boston Tea Party, among others. The city is also known for its world-known Boston Marathon Race, and the various parks in its vicinity like the Franklin Park. Also, you shouldn't miss the opportunity to enjoy the tasty local and international cuisines in some of the famous places to eat around town like the Chinatown restaurants. We have prepared a list of some of the best inexpensive Airbnb rentals that you can stay while in town. Read more to take a look at cheap Airbnbs in Boston, Massachusetts, USA.
Houseboats
8 Best Airbnb Houseboats In Boston, Massachusetts - Updated 2025

As the capital and most popular city in Massachusetts, Boston is not a city you want to skip for a vacation. Renowned for its delicious baked beans and jazz bars, it has so much more to offer. It boasts attractions that will bring your vacation to the next level. Visit New England Aquarium where you can find a giant ocean tank filled with up to 2,000 different aquatic species. Soothe your soul and have a leisure walk along the Boston Public Garden. Art enthusiasts can stop by the Museum of Fine Arts, Boston, whose stunning collections include masterpieces from Oceania and the ancient world. Of course, to explore Boston in its entirety you'll need a comfortable stay. There are hotels with a rooftop pool or stylish Airbnbs for the ones looking for luxury. But why not make your trip all the more fun by living in a houseboat? You can experience living on the waters as you unwind and watch the horizon. Plan your itinerary and book a yacht rental now. Keep reading to know about the best Airbnb houseboats in Boston, Massachusetts.
Vrbo
17 Best Vrbo Vacation Rentals In Downtown Boston, Massachusetts - Updated 2025

One of the best things about Massachusetts’ largest city is that it is a very versatile and diverse city. People come to visit Boston for all kinds of reasons - some for business, others for relaxation. Some come here for seafood and clam chowder, while others love exploring the city for its history and architecture. One thing’s for sure; the reasons are plentiful. One of the best areas to stay in when traveling to Boston is its downtown neighborhood, as you’ll be close to all the iconic landmarks, the Financial District, and also be surrounded by restaurants, shops, bars, and entertainment options galore. To make it easier for you, we’ve gathered the best accommodations in downtown Boston. Whether you’re a solo or business traveler, coming with the kids or your fur baby, we’ve got you covered. Check out this list of the best Vrbo vacation rentals in downtown Boston, Massachusetts.
Airbnb
Top 28 Airbnb Vacation Rentals In Downtown Boston, USA - Updated 2025

The city of Boston, Massachusetts is not only one of the United States’ most beloved cities, but it’s also one of the most visited, with close to 20 million projected visitors according to their local tourism board statistics. It’s not hard to understand why – besides delicious street food and a plethora of shopping spots, the city is an invigorating blend of history that dates back to the country’s origins and the numerous innovations in various industries here. While in Boston, visitors can join fun day tours and soak up a great deal of fun and culture in neighborhoods like Beacon Hill and Back Bay. For those looking to visit, the city has a high supply of vacation rentals that will allow you to maximize the thrill of being there, particularly in the downtown area which has a lot of attractions. Read on for more information on the top Airbnb vacation rentals in Downtown Boston, USA.
Airbnb
12 Best Airbnb Vacation Rentals In Jamaica Plain, Boston, Massachusetts - Updated 2025

Popularly regarded as one of the best places to live in Massachusetts, Jamaica Plain is a charming neighborhood. “JP” as it is locally called is a neighborhood that has an elegant urban feel and is filled with places you can spend time relaxing. This beautiful place was once called the “Eden of America” for its quaint farmlands and mesmerizing landscapes. From its picturesque ponds to the Arnold Arboretum which offers stunning landscape views, and its new parks, there are more than enough places to stroll and relax in JP. Food lovers and shoppers are not left out. There are several exquisite restaurants and bars to dine in, charming cafes, and of course, quality shops to cater to your shopping needs. So if you are heading to JP for your vacation, you do not necessarily need to spend money staying in hotels. Camp out at an Airbnb vacation rental as you explore the most romantic places and hit all the best nightclubs in Boston. Check out this list of the best Airbnb vacation rentals in Jamaica Plain, Boston, Massachusetts.
Airbnb
15 Best Airbnb Vacation Rentals In And Near East Boston, Massachusetts - Updated 2025

East Boston or Eastie as its sometimes called is home to over 40,000 citizens. This region welcomes immigrants from different areas of the world, some of who have permanently sunk their roots in its soils. Boston gets frequent visits from business persons, history buffs, or holidaymakers who want to explore the region. With great landmarks such as the Piers Park, Suffolk Downs, Santarpio’s Pizza Spot, Eagle Hill Historic District, East Boston enjoys much attention from tourists. Visiting Bennington Street Burying Ground and Donald McKay House are also among the popular things to do here. Whatever your reason for going to this area may be, choose to relax at one of the following best Airbnb vacation rentals in and near East Boston, Massachusetts.
Airbnb
13 Best Airbnb Vacation Rentals In And Near Boston Waterfront, Massachusetts

What is the most touristy thing to do in Boston? Visiting the Boston Harbour Waterfront, of course. For those of you who might not know, the Boston Waterfront is basically a series of walkways right in front of the Boston Harbour. That means hotel rooms with water views, open-air bars to drink in while you hear the sound of the waves and restaurants that serve the very fresh catch of the day. It also means that you can walk to the waterfront from your vacation rental, or you could just walk along the streets of the Financial District since you're going to be living in the heart of the city! So, if you are planning a trip to Boston Waterfront, then check out this specially curated list of some of the best Airbnb vacation rentals in and near Boston Waterfront, Massachusetts.
Airbnbs With Pools
Top 10 Airbnbs With Pool In Boston, Massachusetts - Updated 2025

A popular tourist destination for scholars, sports fans, history buffs, artists, and everything in between, Boston is a progressive and forward-thinking city known for its world-changing innovations and its large roles in the American Revolution. Having such a great history, many people visit the area for its museums and historical places such as Faneuil Hall and Old North Church. Boston is also known for some of the world's most famous sports teams, such as the Red Sox in baseball, Patriots in football, and Celtics in basketball. Visitors will also love the stunning views of skylines, panoramic waterfront views, city lights at night, and the unique mix of old-historical buildings and modern skyscrapers in the area. Foodies will also enjoy the dining scenes of sushi restaurants and cocktail bars. Primarily a dense concrete jungle, rentals that have swimming pools can be a bit hard to find in this city. To help you find a great place to stay, read on for a list of the top Airbnbs with pools in Boston, Massachusetts.
Unique Airbnb
5 Most Unique Airbnbs To Stay In Boston, Massachusetts - Updated 2025

There are only a few cities in the country that are as rich in colonial past as Boston. Freedom Trail is a good example. It is lined by 16 historical monuments, such as Granary Burying Ground in Massachusetts, King’s Chapel Burying Ground, Massachusetts State House, Old State House, and Paul Revere House. When you begin your itinerary on Freedom Trail, ensure that you take brochures at Boston Common. The city also has a vibrant arts and culture scene, so visit famous museums, such as Arthur M. Sackler Museum, Isabella Stewart Gardner Museum, and Museum of Fine Arts. If you are on a leisure trip with your family, New England Aquarium might interest you. Discover the most unique Airbnbs to stay in Boston, Massachusetts, below.
Cabins
6 Best Cabin Rentals Near Boston, Massachusetts - Updated 2025

Known as the birthplace of the American Revolution, every cobblestone corner, avenue, and neighborhood of Boston takes you back in time. There's so much to do in this culturally rich city, you will have trouble deciding which one to pick first. There's the Freedom Trail, which takes you on a 3-mi (4-km) walking tour across 16 historic sites such as the location of the Boston Massacre, Old State House, and many more fascinating places. Boston is also home to the beautiful Charles River, many parks, and a charming metropolitan scene. So, if you want to cross off this amazing city from your bucket list, take a look at the best cabin rentals near Boston, Massachusetts.
Yoga Retreats
Top 3 Yoga Retreats In Boston, Massachusetts - Updated 2025

Boston is considered one of the most important cities in the United States with respect to its cultural and historical offerings. Aside from being the state capital of Massachusetts, it is also home to the historic Freedom Trail and the oldest city park in the USA, Boston Common. Stroll the gorgeous streets of Beacon Hill while admiring Victorian architecture and explore one of the most affluent avenues in the world - Newbury Street. After wandering around, have your fill of the delectable treats from Quincy Market and Faneuil Hall Marketplace. With so many things to do and discover while in Boston, it's crucial to maintain a healthy lifestyle and keep stretching your muscles amid this bustling city. Read on to find the top yoga retreats in Boston, Massachusetts, for a tranquil and wholesome stay!
Fishing Lodges
11 Best Fishing Lodges Near Boston, Massachusetts - Updated 2025

The tradition of fishing runs deep in Massachusetts. The region is naturally blessed with many freshwater and saltwater sites. Many communities in Massachusetts look to fishing as a source of livelihood. It is not surprising, therefore, that fishing has been among the most popular tourist activities in the state. Being a family-friendly activity, fishing is a great way for family members to spend quality time together. For busy professionals, it can be a simple way to unwind, breathe for a while, and reconnect with nature. It is a fulfilling activity that many look forward to, especially in summer, and you will also find some of the best things to do in winter. You can go on a fun fishing trip when you stay at a lovely lodge. Check out some of the best fishing lodges near Boston, Massachusetts.
Airbnb
12 Best Airbnbs Near Boston South Station, Massachusetts - Updated 2025

Considered New England's busiest bus and train hub, Boston's South Station in Massachusetts is an area with lots of things to do. A great variety of fine eateries but also food trucks will make sure you'll never go hungry around here. The proximity to other notable Boston neighborhoods is great, so you will be able to walk pretty much everywhere from here. Freedom Trail is perhaps one of the most fascinating things to do because, during this walking tour, you will learn about the American Revolution and beyond. Have a look at the best Airbnbs near Boston South Station, Massachusetts, below.
Airbnb
13 Best Airbnb Vacation Rentals On And Near Newbury Street, Boston, Massachusetts - Updated 2025

The city of Boston is not only the capital of Massachusetts but also one of the oldest cities of the United States, and this is evident in the city's art and architecture. Rightly so, the city is the economic and cultural epicenter of Massachusetts. The University of Boston is one of the best universities of the United States, and it makes Boston the hub of higher education and a place for young and vibrant hearts. All this and much more has led to the making of Boston as a major destination. To cater to the increasing number of tourists, students, and art patrons, the city has varied accommodation choices ranging from luxury hotels to holiday homes. Out of all these places to stay, we have selected the best Airbnb vacation rentals on and near Newbury Street, Boston, Massachusetts. Read on to find the one that suits you.
Pet Friendly Airbnb
13 Best Pet-Friendly Airbnb Vacation Rentals In Boston, Massachusetts - Updated 2025

Massachusetts’ capital Boston is a perfect blend of history and modernity with various things to do. It is also the cultural and economic hub of Greater Boston. From the Museum of Fine Arts, to Boston Public Library housing more than 6,000,000 books, from Trinity Church, to Boston Children’s Museum--it has something for everyone. The New England Aquarium and Museum of Science are some other attractions to explore. Boston is also famous for its food and shopping space. It has both open-air marketplaces and shopping arcades to suit the taste of all kinds of shopaholics. Boston is home to a number of companies and therefore sees lots of business travellers as well. So, whether you are on a family holiday or are a business traveller who has decided to take your pet along for the trip, there are a number of pet-friendly accommodations in this place. Check out the best pet-friendly Airbnb vacation rentals in Boston, Massachusetts, below.
Airbnb
10 Best Airbnb Vacation Rentals In Watertown, Massachusetts - Updated 2025

Watertown lies in the Greater Boston region of Massachusetts along the banks of the Charles River. Driving distance to Boston, Harvard, and MIT, the city’s a hotbed of historic sites and cultural attractions. Prominent landmarks include Commander's Mansion, Edmund Fowle House, Gore Estate, and Perkins School. The meandering Charles River offers ample opportunities for outdoor activities such as hiking, biking, kayaking, or boating. Mount Auburn Cemetery, the country's first cemetery garden, evokes calmness with its rolling landscape and houses Washington Tower where you get picturesque views of Boston. With its vibrant art scene, foodscape, and thriving nightlife, Watertown has plenty to keep you busy. Enjoy the city like a local by booking a vacation rental which grants comfort and privacy at reasonable rates. Here is a list of the top 10 Airbnb vacation rentals in Watertown, Massachusetts, to get you started.

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