We are taking the train from New York to Boston on Thursday August 31. We plan to stay at a hotel in south Boston that evening so that we can go by rented car to Chatham early on Friday morning, September 1.

Two questions:

Can you suggest a hotel that would provide a good jumping off place toward Chatham--avoiding the "Big Dig" etc.?

Can you suggest a car rental agency near that hotel?

Looking at a map Brookline looks convenient but I seek your local advice--no websites please. Thanks!

Anthony

Your map might need rotating -- Brookline is not a good choice, since it's west of Boston, not south. The Big Dig is the heart of Boston and you will deal with it in getting from the airport to your hotel.

I would recommend that you rent your car at the airport and stay at a hotel near the Expressway (Route 93 or Route 3) such as the Marriott in Quincy so that you will have a head start on Friday morning. Otherwise, you'll be dealing with getting from the airport to the hotel without a car on Thursday.

There is also a Sheraton in Braintree .. which is a great location if you are heading to the Cape ... (Sheraton (781)-848-7400)You can hop on Route 3 and go straight to Route 6 into Chatham .. in probaby an hour or so ... depending on traffic and timing traveling route 3 .. and I agree I would probably rent a car at the airport unless the Sheraton provides pick up at the airport .. and if not you can take the Logan Express Bus to Braintree .. it is almost next door to the hotel .. and I know Enterprise Car Rental will deliver a car to your doorstep hotel or otherwise .. other agencies may offer to do the same .. Enjoy Chatham .. it is so lovely .. !

We are arriving in Boston by train not plane. Can you take a cab to Braintree then get a car at the Marriott or Sheraton?

So sorry ... your message states that clearly ... Here is another option .. see if you can depart the train at Route 128 station ... I often take the train from Route 128 station into Penn Station ... If so .. get off at the Route 128 station .. you can stay at the Dedham Hilton
25 Allied Dr
Dedham, MA 02026
(781) 329-7900
(very close by ... less than five minutes from the train station) ... They probably have a van/car that will pick you up if you call ahead and if not there is an Enterprise Rental Car in Norwood also very close ... and arrange to pick up your car at the 128 station by calling ahead to Enterprise which is very reasonable ...
From the hotel .. you would get right on Route 128 South .. follow to Route 3 South and then right on to Route 6 into Chatham .. very easy .. and probably takes about 1 1/2 hours maximum driving time from your Dedham hotel into Chatham ... Also the Dedham Hotel is a nice hotel .. located 10 miles outside of Boston ... hope this helps ... !

What works for me - pick up rental car and spend the night in Plymouth. Get up early and beat traffic and have a big breakfast on the cape.

I apologize for the train/plane confusion.

If you take the train all the way to South Station, you can then take the Red Line subway to Quincy or Braintree and take a cab the rest of the way (a mile or two) to the hotel although I believe they offer shuttles, or IIRC you can get a rental car at South Station.

IMHO this is less elaborate than the 128/Dedham strategy, especially since Dedham is west of Boston and Braintree is south -- if you do stay in Dedham, you'll end up driving right past the Braintree Sheraton on your way south the next morning. You might try calling the Sheraton Braintree and the Hilton in Quincy regarding the available options for car rentals, and shuttles.

Sorry, that's a Marriot (not Hilton) in Quincy.

If I were taking a train from NYC and my destination was the Cape, I'd get off in Providence, rent a car there, and avoid Boston altogether.

The distance and driving time from Providence to Chatham is virtually identical to the time and distance from Dedham, and of course the net travel time would be much less than if you spent an extra hour traveling by train from Prov to Boston and then started heading south. (This whole pargraph makes more sense if you have a map in front of you.)

The Providence suggestion is a great one. The Courtyard Marriott and the Westin are steps away from the Amtrak station; and AVIS has a rental office at 1 Dorrance St, which is also right there. Pick the car up next morning and you're set.

However, if you take the train to Rt 128 ... there is a hotel very close .. and if the Hilton picks you up .. it makes it very simple in my mind .. without having to take another train ride etc .. Getting off in Providence is another good option .. if you are arriving at a time when you wouldn't mind hoping in a car and driving the distance to Plymouth or to the Cape and that would also be true of Dedham .. if you wouldn't mind driving when you get off the train .. it is again only 1 1/2 hours from Dedham to Chatham .. maybe you would prefer to get the drive over .. Whatever you plan .. have a great visit on Cape .. !

I would take the train to Providence and rent a car. Chatham is 2 hours form Providence but it's not a bad drive. If Cape Cod is where youwant to be...I say get there asap!