If you want to combine sightseeing with relaxing elements, Boston has lots of great places to stay. Its historic neighborhoods are pedestrian-friendly, and many of these offer access to some unique sites. Booking a Boston vacation rental lets you get a closer look at pivotal events and experience this city like a true local. With so many amazing neighborhoods to consider, we’ve put together this guide for you to browse. Below we’ll jump into some more detail about which iconic neighborhoods you should be considering. We’ll also give you some insight into what sites and activities you should check out once you’ve decided on your perfect place to stay in Boston.

Beacon Hill

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Beacon Hill is a neighborhood in Boston with lots of red brick buildings and cobblestone streets. It also has some of the best places to visit, including Boston Common, Massachusetts State House, and Boston Public Garden, so it’s popular for walking around and sightseeing. Take the Freedom Trail from Boston Common to step through history. This area is beautiful, but also has one of the higher price tags attached to it. If you’re looking for somewhere that offers budget options, this won’t be that place.

Pro Traveler TipIf you end up staying in Beacon Hill, make sure to check out Figs, an incredible pizzeria that’s serving up some pretty inventive pies. Try the Fig & Prosciutto pizza. It won’t disappoint.


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Charlestown used to be its own city before it joined Boston in 1874. It’s home to historic sites such as the U.S.S. Constitution, the Charlestown Navy Yard, and Warren Tavern. Aside from its historical merit, Charlestown is also one of the oldest neighborhoods in the city, having originally been named Mishawum by the Massachusett tribe. Although sitting slightly left-of-center, Charlestown is a quick hop, skip, and a jump from downtown. A bridge quickly takes you into central Boston, so it’s also a convenient place to stay.

Pro Traveler TipWhether you choose to stay in this neighborhood or not, it would come highly recommended that you make a trip there. Once in Charlestown, be sure to check out Boston’s Freedom Trail. It would also be a good idea to jump on one of the tours. Check out this link when you’re ready to book your tour.











Boston’s Chinatown is small, but it’s packed with restaurants, cafes, and stores. The Leather District, which is Chinatown’s neighbor, is also a good option for accommodation. It’s filled with converted warehouse lofts, so you can sometimes find some real gems when it comes to vacation rentals. The Leather District is right next to Chinatown and boasts some really beautiful brick warehouses. These warehouses, built in the 19th century, have been converted into incredible loft apartments and make great options for rental places for your Bostonian trip.

Pro Traveler Tip: Boston’s Chinatown and the Leather District alike boast some pretty phenomenal restaurants. But out of all the culinary gems packed into this area, Troquet is the go-to for fabulous French wines and cuisine. If you’re looking for something other than French, be sure to check out this list of the other top places in the neighborhood.

The South End

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The South End attracts a fashionable crowd, and it’s filled with trendy restaurants and boutiques. However, despite its reputation as the place to be for the upwardly mobile, it still maintains somewhat of a diverse atmosphere, giving it an air of authenticity. The South End is by far the most stylish neighborhood in Boston. You’ll find some incredible lodging options here but be warned: the stylish elegance comes with a price tag. Aside from the lodging, be sure to dig into some of the food here. The restaurants are fabulous. If you like to do a little shopping while on vacation, this neighborhood has no shortage of lovely clothes.

Pro Traveler TipShopping while on vacation is a must for some of you. Ladies, be sure to hit Flock for some of the latest and greatest in women’s fashion. And fellas, you’ve got to check out Sault. This place is packed with traditional Bostonian style.

Bay Village

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Bay Village is a good option if you want to stay somewhere central. This small neighborhood is right in the middle of the city and has plenty to see and do on its own, from lively clubs to scenic streets. Because of its location, you can also easily explore other parts of the city on foot. Although the smallest neighborhood in Boston with only 25 acres, don’t let its size fool you. These neighborhood blocks are packed with action and fun for you and your party. After all, this is the neighborhood that can claim to be the birthplace of none other than Mr. Edgar Allen Poe. Bay Village is rich in architectural styles as well. Here, you’ll find some of the Federal row houses that you’d find in Beacon Hill right next to some Art Deco touches right next door in the old film distribution area.

Pro Traveler Tip: There is a ton to do in Boston as a whole. Really consider Bay Village if you’re looking for someplace intimate with close proximity to all the action. As a central hub, this neighborhood offers you all the activities the city has to offer, while still staying isolated from all the craziness of nightlife in the rest of the city.

Back Bay

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Back Bay is one of the most popular places in Boston for shopping, with a strip of stores stretching along Newbury Street. It’s also very scenic, with plenty of Victorian homes to go around. In stark contrast to the above neighborhood with a more Federal rowhome-style, Back Bay is much more Victorian in architecture and will give you a totally different look and feel as you wander the streets. The beautiful Boston Public Library is right in the middle of the neighborhood, and you should definitely pay it a visit while you’re in town.

Pro Traveler Tip: Abe & Louie’s is an institution in the way of steakhouses and comes highly recommended by both travelers and locals alike. They also have a gorgeous location in Boca Raton, Florida, a great choice for another trip.

The North End

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The North End has plenty to offer when it comes to historic sites. The Freedom Trail runs through the neighborhood, passing by sites like Paul Revere House and Old North Church. If you like Italian food, this is a wonderful place to stay; it’s loaded with Italian restaurants and delis. This place is loaded with great food and tons of history. If it isn’t already, make sure the North Loop is at the top of your list for neighborhood considerations.

Pro Traveler Tip: Make sure you check out all the tours available to you in this area here. With so much history, there’s bound to be one that catches your eye. Don’t miss out on these great activities in one of the most historic neighborhoods in Boston!

Harvard Square

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If you want to get a feel for life at Harvard University, stay in or around Harvard Square, or at least visit it for an afternoon. This historic area has lots of book stores, letting you hone your intellectual side. Enjoy great food and cool bars or just spend some time people watching for a while. With such close proximity to the campus, this neighborhood is home to some great water holes. Regardless of your preferences from collegiate to sophisticated, this area’s got it all.

Pro Traveler Tip: This area hosts a ton of great events throughout the year. It’d be a good idea to give the events calendar a look before your trip to plan accordingly.

Jamaica Plain

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If you’re looking for a place for some rest and relaxation, give Jamaica Plain a try. This neighborhood is home to Jamaica Pond, a peaceful pool of water on the southwest side of the city. Enjoy an afternoon strolling around the pond and then head over to Samuel Adams Brewery next door in Egleston Square to taste some of the famous brewery’s wares. The brewery’s tours are absolutely legendary and known internationally. Click here to find out more and get your tickets squared away today.

Pro Traveler Tip:This area has a strong Latino population and as such boasts some pretty great restaurants. Make a point to check out Casa Verde Taqueria and Chilacates for your trip if you decide on this neighborhood.











Dorchester is huge, so you can find lots of options as far as places to stay are concerned. This diverse and historic area has a lot of character and a thriving nightlife scene. Boston is packed with culture and Dorchester is a big part of that. The neighborhood is home to the very first Vietnamese Community Center in the country. As such, you’ll find a ton of great Vietnamese food in this part of town. After a quick bite, head over to one of its many Irish pubs or check out Dorchester Brewing Co. for some local microbrewery fare.

Pro Traveler Tip: Franklin Park is possibly the most beautiful park in the whole city and is located right in the heart of this historic neighborhood. Should you choose to stay here, be sure and check out this spectacular slice of nature in the city.

Head To Boston For Your Next Getaway

This beautiful city is full of historical and cultural gems. From being the birth of iconic figures like Paul Revere and Edgar Alan Po to being the site of the first Vietnamese Community Center, there is no shortage of history here.

We’ve walked you through the top neighborhoods to consider above and now ask you: which one will you choose? Head over to VacationRenter now and book your next trip!