Where should I drop off rental car near Boston?
 

Toward the end our our New England vacation, we'll be driving down from Portland, and Boston will be our last stop for a couple days before flying back to San Francisco. I have read the recommendations to avoid driving into Boston, so I'm thinking that it might be better to drop off the rental car somewhere north of downtown Boston and take Uber or a taxi in.

Of course, the closer I can drop it off, the less expensive the ride into downtown. I'll likely be renting from Enterprise, so I'm looking for advice on ease of accessibility from the highway to one of these Enterprise locations:
- Downtown at 1 Congress Street (very close but should I avoid this location?)
- Logan Airport at 15 Transportation Way (3.5 miles away)
- In Chelsea at 324 Marginal Street (3.5 miles away)
- In Revere at 55 American Legion Highway (6 miles away)
- In Somerville at 37 Mystic Avenue/Sullivan Square (4 miles away but off the direct path a bit)

If you choose to drop off in Somerville, the location is next to (the overhead at that point) route 93. (Take route 95 south from Maine to the 128/95 ring around Boston, continuing south--the sign says "Waltham" iirc--, to route 93 south)

If you don't have a lot of luggage, you could then walk a few minutes over to the newish Assembly Row stop on the Orange line subway, which would take you into downtown Boston to connect to the subway line to the airport.
You would have to call a taxi, since not many of them sit around waiting nearby. I'm sure the Enterprise office could help you get the number for Green and Yellow taxi in Somerville.
Or of course, there is Uber.

IMO Chelsea and Revere might be more confusing since they involve secondary and surface roads.

Or just try for direct to the airport. The so-called horrors of driving in Boston are way overblown! (unless it is rush hour, at which time all bets are off --on any road).
Same directions: Take route 95 south from Maine to the 128/95 ring around Boston, continuing south--the sign says "Waltham" iirc--, to route 93 south, with the addition of "to the airport tunnel".

Which car rental company and where in the city are you staying? You'd probably have no problems if you can return the car at a low-traffic time.... but that would depend on day of week, time of day etc.

Getting to Congress Street is not that difficult - at least for me who lives here, with prepared directions. It will save you valuable travel time.

Otherwise I'd go to the airport and take the Back Bay shuttle or the free Silverline shuttle to South Station depending on your final destination. Are there alternate drop off locations fees?

I can also say that driving INTO Boston is not nearly as confusing as trying to get out. While there are a lot of one-way streets, I can't say that driving in downtown Boston was that confusing with a GPS, and you will save a lot of time by driving straight to your lodging unless you're arriving in the middle of rush-hour. It's considerably harder to get out of Boston because you have to find the correct entry point for the tunnels, which can be confusing if you aren't familiar with the city. (Obviously, it's easier to drive in on a weekend, but I've done it on a Friday before, and it's not that bad.)

Otherwise, I tend to agree that the best place to drop off the car would be the airport. Then you could take a taxi or the T into Boston.

Are they not going straight to the airport for a flight out?
The concern seems to be driving in Boston.

Where are you staying?

Dropping the car at the airport is simple. Come down 95 to Rt. 1, South, then take Rt. 60 to 1A to the airport. Do you know what day you'll be doing this?

Nope, I misread.
So, yes, OP, where are you staying in Boston?

Thanks to all for the informative replies so far. Our vacation isn't until Sept/Oct 2017, when we will be visiting upstate NY, VT, and ME.

Like some, I'm a bit anal retentive about advance planning and getting the best lodging set up in advance. I have come to find out that some of the best B&Bs in Vermont are already booked for fall foliage time next year, so I will be booking ASAP.

SambaChula and doug_stallings, your responses make me feel that I should be able to drive to the Congress Street location as long as it is not at a bad time of day. Our plan right now is to arrive on a Sunday or Monday afternoon. I assume that Sundays are good, and Mondays before 3:00 should be OK as well, am I right?

I don't have a hotel in Boston yet because we haven't decided what to do while in your fair city....still researching how to spend our time. I'll be looking for something under $250 a night and suggestions would be welcome.

@hotboy01--
Driving in downtown Boston, trying to find an address (Congress Street), GPS or no, is a lot different than just getting off a highway exit and going directly to an E office or getting off a highway exit directly into the airport tunnel. I would suggest that keeping to the major highways and avoiding surface streets as much as possible would make the process much simpler. Then take a taxi to the hotel.
If you are adventurous enough to try surface streets with a GPS, you might think about first dropping off your luggage at whatever hotel you choose, then dropping off the car at the nearest E office, probably Congress Street, and taking the T back to the hotel, hands free.

We did not find picking up and dropping off a rental car downtown to be difficult at all. We stayed at the Lowe's (which was great, if you can get a rate within your budget) and walked over to a big garage that housed all the major rental car companies--don't know the address, perhaps it's Congress St. Easy peasy.

NewbE, do you mean the Loews Hotel? Not to be confused with Lowe's Home Improvement Store.

Oh, my, I think it would be hard to stay at a Lowe's--they don't even sell beds. LOL Picky picky

Oh ffs. Of couse I meant they should stay at a home improvement store, lol.

Driving into the city is not a big deal outside of rush hour. On a Sunday, should be fine.

I would think your bigger problem would be finding a hotel for <$250.

We always pick up and drop off at the airport. Easy getting there and back into the city.

If you haven't booked a hotel, I'd wait to decide on the rental car and choose the location nearest your hotel.

Driving in Boston on a Sunday isn't that bad, FWIW.