We will be heading out of NYC to Lenox,MA. The last time we did this we took the train to Poughkeepsie and Hertz picked us up @ the train station. We spent 2 nights @The Beekman Arms in Rhinebeck before heading to Lenox. This time we are thinking we will go straight to Lenox. Is Poughkeepsie still the best point at which to depart the train or is there another stop more reasonable?

Wouldn't Wassaic be closer?
http://www.mta.info/mnr/html/mnrmap.htm

Wassaic is in the middle of nowhere - no rental car anywhere nearby, plus the ride to Wassaic is a lot longer ride than to POK.

POK would be ok but not the best option.

My #1 choice outside of NYC would be North White Plains. There is a Hertz office walking distance from the station - it's the 66 Haarlem Avenue location. It's a 35 or so min ride from GCT.

If it were me I'd just rent right in NYC and drive out of town. As long as you're not leaving town at rush hour it's usually pretty smooth sailing. For Lenox I'd take West side hwy past the GWB, over the Henry Hudson Bridge straight to the Saw Mill River, then onto the Taconic.

From White Plains location I'd take I287 over to the Saw Mill North, which runs into the Taconic.

How about Danbury CT or Brewster NY

Nope. Most trains to Danbury require a change in S. Norwalk, and take over 2hrs to get to Danbury.

1.5 hrs from GCT to Brewster and still no rental car.

I know what I'm talking about here - drive from the city or rent at Hertz North White Plains.

J62 is right. The best solution is to rent a car...and, to me, that should happen in the city. It's the most practical and probably the least time-consuming and least expensive!
Lenox is not convenient to any Metro North station

When I went to the Albany area (Kinderhook to be specific) last summer, I also found it much easier---not to mention $30 per day cheaper---to rent a car from Hertz at North White Plains. The station is blocks from the highway to the Tappen Zee Bridge, and then it's an easy drive up to the Albany area, from which you can easily get to Lenox.

While it's certainly easier to rent a car in Manhattan, I just find it so expensive. I have recently gotten very good rates (for Manhattan) for a rental from Alamo ($66 per day), but it was $53 per day from Hertz, though their rates are up since last summer. Price out the options, but it's so easy to get to North White Plains that I think it's your best shot. The office is directly across the street from the train station.

FYI: It's usually cheaper still to rent in New Haven, which is at the end of the Metro North line, but it takes a long time to get there, and Amtrak is significantly more expensive.

Doug, I disagree with a couple of your "directions."
First of all, while you can take the Tappan Zee Bridge and go via the NY Thruway, it's not the best route to Lenox, Massachusetts.
Second, you wouldn't be taking a Metro North train to New Haven if your destination is Lenox, Massachusetts. Instead, it would either be the Harlem line (to White Plains) or the Hudson line (to lower Hudson Valley).
Further, while it might be a little more expensive to rent a car in NYC rather than White Plains, it would certainly be an easier trip and probably time consuming to do the former.

Are you headed for Tanglewood? There are buses that go directly there - nowhere the freedom you have with a car, but just thought I'd mention the option.

Once you rent your car In NYC you; might head up the Hutchinson River Pkwy to the Taconic Pkwy to I90 (that's an "i") and go east to US Rte 7 north to Lenox.

From Manhattan to the Hutch? I don't understand that route. Saw Mill River, Major Deegan or Bronx River maybe, but Hutch?

I would go to N White Plains or Stamford, CT. Either one have a car rental place walking distance from the train. Both are easy rides out of the city and the car rental will be cheaper than in Manhattan.

For Manhattan to Hutchinson Pkwy, take Henry Hudson out of the city and stay on it. Don't go into I-95. You will have to pay a toll on the Henry Hudson Bridge, around $2. Take exit for Hutchinson later. But I-87 has an exit from Henry Hudson before you get to Hutch. There is another exit later from Hutch to I-87 towards Albany.

Stamford is very easy to rent car. Both Hertz and Avis are across the street from Metro North station. And I've found rates there to be half of Manhattan.

You guys are mistaking the Hutchinson for the Cross County, which goes to the Hutch. (which runs from the Whitestone Bridge to the Merritt in CT).

Jeez, oops. Sorry. I had the poor poster skipping the H. Hudson Pkwy. Then the Cross County and then the Hutchinson. Then again they could go via the East Side. FDR to Triboro/Kennedy Bridge to Bruckner/New England to Hutchinson etc. Or OP, rent your car at the rental place on 83rd betw. 1st and 2nd, go over to York, left on York to FDR. to Kennedy/Triboro Bridge. I'm dizzy already.

I agree with J62. One thing about Metro North is that the fares are so expensive. Yes, you save in car rental fees, but if you're renting for a shorter trip, crunch the numbers. An off-peak ticket to Stamford is almost $10 a person. With two people, that's $40, rt. Peak, $50. Plus on a shorter trip, you have less time to work with. Taking the train just sucks up time, and if you are traffic savvy getting out of the city, you might be better off renting in the city.

It's well worth it renting out of the city for a week, where a week from the city might cost $500 and the from North White Plains, $275.

I really hate renting outside the city when you have lots of stuff. Drop your stuff back home. Schlep back to NWP. Schelp back on the train back to NY.

If we only had a train system like they do in Europe, I'd use it in a NY minute.