8 Top Tips For Renting a Car in Boston Massachusetts

Best Boston Rental Car

Renting a car in Boston is the best way to explore Massachusetts, and even other parts of New England! However, there are a few things you should know before you pick up your Boston rental car. Follow along as we share some easy tips so you can have the best experience on your upcoming trip. Whether you’re renting a car in the city of Boston or exploring a different part of MA with a car hire, we got you covered!

Our Boston Rental Car Story

So what makes us Boston rent a car experts? Well, before we started our travel blog we actually attended university in Boston and lived there for 8+ years! These days we fly back to this area of the United States often to visit family. 

Historically, our move has been to fly into JFK International Airport. However, in more recent years we have tried to go through Boston as it’s smaller and more convenient. This has given us a lot of experience renting a car in Boston and helped us to provide you with these 7 helpful tips!

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Boston Rental Car Travel Tips

8 Tips For Renting a Car in Boston

1. Planning Your Road Trip

The first thing to decide before booking your Boston car rental is where you’re actually going! Boston is a popular starting point for travelers visiting from the USA or abroad. 

While renting a car in New York is another option, the flight deals can often be better going through the largest city in Massachusetts. When booking any flight we always check Skyscanner first. This will compare all the different prices for you so you can figure out where to fly into.

Boston and New York are the most popular airports for travelers visiting New England. Yet, if you’re heading to the area you should thoroughly consider your route.

Are you heading to Maine, Vermont, or somewhere in northern New England? Then without a doubt Boston is the better airport to fly into. Flights to New York may technically be less expensive, but you will have to factor in extra tolls, and driving time.  

Once you have your dates it’s time to start planning your trip to Boston. Are the beaches of Cape Cod calling you, or would you to prefer spending a nice relaxing weekend in the Berkshires? How about just driving from town to town?

The locations and how long you need to rent a car in Boston are all things to consider. Also, make sure to ask for the weekly rate as it is a great way to score deals.

Renting a Car in Boston Guide

2. Don’t Rent a Car For Boston!

One of the biggest tips we can give you is to not rent a car during your stay in Boston. Many people visiting Boston will fly into the city first to see it. If you are spending some time here make sure not to pick up your Boston rental car until the day you actually leave.

Trust us when we say you won’t actually need a vehicle in Boston city center! In fact, it will be more of a pain to have than anything, especially during rush hour. Remember that parking spaces can be difficult to find and always expensive. 

The traffic is also not fun in the downtown area, and there are plenty of other ways to get around to the major sights. Keep in mind we’re talking about one of the oldest cities in America. In comparison with other U.S. metropolises the roads can be tricky to navigate. 

Getting Around Without a Boston MA Car Hire

You’re better off using public transportation or ride share apps to get to Faneuil Hall Marketplace, Fenway Park, and the best historical sites. Take advantage of the city bikes, Uber, and other modes of transport instead of renting a car in Boston.

Even if you have to head back to the airport to get your car (the prices are sometimes cheaper) it’s still worth it to avoid having it in the city. Also, Boston’s airport is super close to downtown so it won’t take long to head back. Then you can pick up your rental car for when you want to explore other areas of Massachusetts or New England. 

Also, remember that you can rent a car from one of the branches in Boston instead of from the airport. Companies like Enterprise rent a car even offer a free pick-up service from locations around the city. 

Just compare the prices before you do this. We personally like booking our Boston car rentals so we drop it off at the airport right before flying out to make our travel day as easy as possible. 

Renting a Car in Boston

3. Finding the Best Boston Rental Car

Obviously, if you’re flying into Boston and taking off from there you’re better off renting a car at the airport. However, you should always compare companies to find the best deal.

We always search Discover Cars when renting a car in Boston. We’ve found great weekly rentals as well as a one way deal when we wanted to finish our trip in other cities. It filters the best prices through dozens of different competitors to help in your search for a cheap Boston MA car hire. 

The nice thing about the rental car center at Boston Logan International Airport is the most popular companies are located in the same place. Just last week when we rented a car in Boston and had a great experience!

We picked up our luggage at baggage claim and the bus that transfers passengers to the car rental terminal came in less than five minutes. 

Best Boston Airport Rental Car Company

4. Time of Year

Another thing to look into before picking up your Boston rental cars is the time of year you’re visiting. If you haven’t been to the East Coast of the United States before know that there are four different seasons… And when we say the seasons can be harsh we mean it!โ€‹

If you’re visiting in winter prepare for the possibility of driving in wild conditions. That means you may want to consider the kind of car you’re renting during this time of year. 

For example, in the winter we recommend paying a little more for a large rental with 4 wheel drive rather than luxury vehicles. Aside from holidays, the cheapest month for a rental vehicle will be when the weather turns cold.

Last winter we arrived at the airport after traveling from Spain. Unsurprisingly, we were welcomed with a nasty snow storm that was only getting worse. Thankfully, we were able to make the 2 hour drive to visit our family. We felt much more comfortable during our drive because we booked a sturdy 4 wheel drive car. 

The summer is also a popular time to rent a car in Boston. There are so many great outdoor activities to enjoy in the warmer months. Yet, don’t forget about the fall either! 

The changing of the leaves brings in tourists who take road trips to Western Massachusetts, New Hampshire, Vermont, and upstate New York. This is actually when the Boston car rental prices can be the highest. 

Boston Rental Car

5. Book Boston Rental Cars in Advance

Planning on traveling during the summer, winter holidays, or around the changing of the leaves? Book in advance to secure a cheap car rental and ensure a great experience.

One thing that we always check is the cancellation policy. If you’re using this company to book Boston rental cars know that they offer a free cancellation up to 48 hours before pick up.

This has been one of the ways that we have saved a ton of money while traveling. We try and make our booking as far out as possible. If the price drops or we no longer need the car, we can cancel it with no extra charge.

Boston MA Rental Car

6. One Way Car Rental in Boston

When renting a car in Boston it’s a great idea to look into a one way deal. This allows you to not only to see as much as possible, but to have the convenience of returning to wherever you’re ending your trip. You can even start in one state or city and end in another!

For instance, many travelers looking into renting a car in New England plan a road trip that has them returning back to Boston Logan Airport. Yet, if you want to see a whole other state (or multiple) why not start in New York or Washington D.C.?

There is typically a one way fee to drop at a different location. Still, it may be worth it if you want to experience Boston’s surrounding areas on your vacation. One time we didn’t do this when flying into Boston and visiting New York and we completely regretted our decision. 

Instead of doing paying the extra drop off fee, we decided to just drive the Boston rent a car back to Logan Airport. Not only did we pay more then the drop off fee in tolls and gas, but we got stuck in an epic traffic jam which turned the four hour drive into six. This won’t work for everyones flights and schedules. However, depending on your route it’s definitely something you should consider. 

Renting a Car in Boston MA Guide

7. Tolls & Fees

Something to watch out for when renting a car in Boston is the tolls. They are all over the highways and particularly expensive when you get towards the big bridges heading in and out of the city.

We recommend asking your Boston car rental company about this when you pick up your vehicle. Some companies offer a daily toll rate while others do a pay as you go. There are actually no manned toll booths in Massachusetts now. Instead, cars are charged automatically and the toll pass comes with your vehicle.

With our last Boston rent a car they offered us something crazy like $27 per day set rate for unlimited tolls. Considering we had a three week rental without many days on the highway it didn’t make sense at all.

We were also told that if we didn’t purchase anything they would charge an additional $6 fee whenever we passed through a toll which would add up very fast. We decided to pay $3 a day to use their pay as you go toll pass. 

Honestly, at that point we had been traveling for over 48 hours and werenโ€™t thinking clearly. Just make sure to ask the rental company about your different options. Don’t let them talk you into the daily rate unless you know you will use it!

There are websites like US Toll Calculations to give you an idea of what you should pay. It’s best to know what will happen beforehand so you won’t be surprised at the end.

Boston Renal Car Airport

8. Checking For Damage On Your Boston Rent a Car

The last thing to watch out for is the condition when picking up your car rental in Boston. It’s so important to check for damage both in and outside of the car before you drive away. With many companies these days, they don’t even bother to walk around the car with you. 

Even though they may give you assurances they know every inch of the car, still do your due diligence. Take pictures, have them mark the contract, and even make a video circling the vehicle. 

As you can imagine, many of these car rentals in Boston have been through a lot! There’s no reason to put yourself or your insurance deductible at risk by not taking these simple steps beforehand.

It’s also essential to make sure you’re insured before renting a car in Boston. Our credit card covers us whenever we’re renting vehicles. Yet, if you don’t have your own form of coverage you’ll want to purchase the additional insurance for an extra fee.

Boston Rental Car Tips

Is Renting a Car in Boston Worth It?

Yes! There are so many fun places to explore around Massachusetts and the New England region. As we mentioned, it doesn’t make any sense to rent a car during your actual stay in Boston. However, if you’re flying into the Boston Airport you can plan an amazing road trip through this part of the United States.

Hopefully, these tips gave you an idea of what to expect if you’re picking up a Boston MA car hire. We know we’ll be getting our next vehicle there very soon!

Have any questions about renting a car in Boston or want to share your own fun road trip ideas? Leave us a comment below!

Safe Travels,
Brigitte & Jake


Boston Car Rental

New England Travel Planning 

 Flights: We always find great flights using Skyscanner and Kayak. This way you can plan your trip around the cheapest and most direct routes.

 Accommodation: Compare multiple sites to get to the best deal such as Booking.com and Agoda! Also, Hostelworld can be your go-to source if you’re traveling on a budget. 

Rental Car: We use Discover Cars when traveling. Consider renting a car in one city and dropping it off in another for an epic road trip! 

Tours: Check out Get Your Guide for hundreds of activities around the country. Book a tour of Fenway Park in Boston, skip the line at the Empire State Building in NYC, or go on a Scenic Boat Tour in Portland Maine! 

 Travel Insurance: Never travel abroad without being covered! We’ve been using SafetyWing for the last few years and they are there when we need them.

 Packing Lists: Find all the inspiration you need with our Amazon packing lists. Including our electronics and camera gear, must-have medical items, and long flight essentials

New England Travel

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