We spent a few days in the Hudson Valley; click on my name to find the trip report.

The Rockefeller estate which is worth a visit is so close to NYC that you might as well pick up the car at La Guardia and make that site your first stop on your tour.

By far the simplest thing to do is to rent a car right at the airport.

Here's a thread from last summer on the region
http://www.fodors.com/community/united-states/hudson-valley-and-catskills.cfm

the OP, abram, also posted in several other threads around that time reporting on their trip. I think their summary is about the best I've seen on Fodors.

We spent six days touring the Hudson Valley in August. It was a challenging trip to figure out because of the varied days that places were open. We also found that our lodging choices seemed to be dunpy motels or fancy B&Bs--not much in between.

If you fly into White Plains (HPN), you're less than 20 minutes from Kykuit, the fabulous Rockefeller estate in Tarrytown--defintiely take the "Grand" tour.

In Hyde Park, we enjoyed the Roosevelt sites--except for Top Cottage, which we thought was a waste of time. The Venderbilt Mansion was also worth a look.

For art, DIA: Beacon is renowned if you like modern art--but we loved Storm King (a huge outdoor sculpture garden) on the west side of the river.

Other places we especially liked: Manitoga (Russel Wright Design Center--arrange for a tour in advance), West Point, Olanna, Walkway across the Hudson, Washington's HQ, Boscobel, a cruise on the Hudson.

The other choice for lodging is mid range chain motels in nondescript commercial areas. Hampton Inn, Courtyard, Holiday Inn Express, etc. Those I listed are in the Poughkeepsie area, about 10min south of Hyde Park on Rt 9.

Abram, we used the chain hotels J62 mentioned for our trip last Spring. We were traveling as an extended family of 8, and I thought the motels were dated & dumpy, and this was not a trip for fancy B&Bs or inns, although there were some lovely ones. Poughkeepsie worked as a good base for us, the sites are fairly close together and the driving was very easy. Also our hotel included breakfast. We did not visit West Point on that trip but I highly recommend it. Be sure to tour the CIA, call ahead for your tour reservation to avoid disappointment.

Here are a couple excellent websites to help you plan your trip:

hudsonvalley.org and hvnet.com

Definitely put Storm King and Olana on your must-see list.

Olanna is fantastic but check the hours.

The Hudson Valley is gorgeous from the train, like the Rhine through Germany. The perfect trip to me would be one way on the train to or from Albany so you can see the scenery, the other way by car, which you will need to get to the sights.

When you are near Hudson (the town with the famous antique stores) it is an easy hop over into the Berkshires for a day or an overnight in Great Barrington or Stockbridge, where there is much to see.

Thank you all for your feedback!! There seems to be so much to see and do in the area, its a bit overwhelming to figure out what to leave in and what to leave out. I think the idea of taking the train is cool. Otherwise, we are having to make a loop to and from the airport with the rental.

If you tell you plan to be in Manhattan for a day upon arrival (or at then end of your trip), then taking a train may make sense.

But as much as I enjoy the train, I think you'll burn a lot of unnecessary time & effort getting from LGA to Penn Station (Amtrak) or Grand Central (Metro North RR (to as far north as Poughkeepsie).

There are many places along the Hudson where you can get as good or better views if you have a car, and you'll need a car once there anyway.

If you're going back to Manhattan at the end of your trip you could drop off your car at Albany and take the train back.

If you haven't booked your flights yet, consider flying into LGA, HPN (white plains) or even SWF (Newburgh), and out of Albany so you don't backtrack.

I just recall you said you're from Austin. AUS-LGA is just beyond the 1500 regulatory limit for non-stop flights so you'll need to connect somewhere if you fly into LGA. Dallas is the best option on AA due to hourly flights on both legs.

For NYC to Austin I much prefer to take a non-stop flight from Newark (Continental/United), or JFK (JetBlue).

Another ps.

Getting from Albany to Austin is a real pain. I know several people who take that trip regularly and some actually drive from Albany to Newark to catch the non-stop flight rather than fly out of Albany.

Steady River
http://www.berfrois.com/2011/12/susan-rogers-hudson-river/

Yes, you see the dilemma, AUS to Hudson River Valley is not that easy/convenient. I think driving from LGA or Newark (better if non-stop), then dropping car somewhere and training back to Manhattan for a couple of nights would work.

Sformby: I live here in the Hudson Valley, A bit inland from Rhinebeck and Poughkeepsie. You are getting good advice from J62 and Abram's thread.

If you have any particular questions I'd be glad to try to answer.

Alright, I'm resurrecting this thread because I am thinking of making this trip next month. Here are my ideas of places to stay and things to do. I know we'll just be scratching the surface, but I don't want to try and do too much. Any help appreciated!

Day 1 (Thurs): Fly AUS > JFK. Pick up a rental car and drive to Tarrytown. Dinner somewhere nice (?)
Stay at Tarrytown House Estate & Conference Center.

Day 2 (Fri): Take Kykuit tour in the morning, see Union Church, then drive to Cold Spring. Walk around Cold Spring.
See 39 Steps at Boscobel / Hudson Valley Shakespeare Festival
Stay at Pig Hill Inn.

Day 3: (Sat) Drive north to Hyde Park. Tour FDR house, Vanderbilt mansion, maybe Val-Kill
Stay at Inn the Woods in Hyde Park.

Day 4: (Sun) Scenic drive from HP, taking in Rhinebeck, finding wineries, etc. Open to suggestions.
Stay at Inn the Woods in Hyde Park.

Day 5-6: (Mon-Wed) Drive to Poughkeepsie, drop the rental car and take Metro North train to Grand Central Terminal. Stay 2 nights in NYC.

You've got a good itinerary, which should be easy to accomplish. As fr dinner in Tarrytown area, how much do you want to spend and what type(s) of food. There are a lot of good choices in the area.
It's too bad you can't fit in a stop at the Storm King Art Center across the river in Cornwall.

It looks good to me. Poughkeepsie is just 10min from Hyde Park. The main attraction at POK is the Walkway over the Hudson, and you can do that any morning, afternoon, or early evening. So your plan to Monday morning drive to POK & take the train and stay in NYC for 2 nights is fine.

As far as I know there is no rental car drop off at the POK train station. Enterprise maybe, but not Hertz or Avis. Their offices are about 10min down the road, so you'd need to take a taxi unless they will shuttle you. You'd need to call the local office directly to inquire.

Tarrytown and Cold Spring are only about a half hour apart so there's no reason to switch after one night. I've actually stayed in Tarrytown House and Pig Hill Inn but probably about 10 years ago so I don't think my detailed impressions would be relevant. But thet are 2 very different kinds of lodging

For dinner in Tarrytown, don't want to break the bank, but seafood maybe? And not too far from hotel.

Metro North website says there is an Enterprise on-site at Poughkeepsie station, but need to confirm.

Google maps says Tarrytown, NY and Cold Spring, NY are 48 minutes apart, to me, probably worth switching. Don't want to drive all the way to Cold Spring from JFK on first day, don't want to backtrack to Tarrytown on second day.

It's about 35 miles from Tarrytown to Cold Spring, so the 48-minute travel-time estimate is pretty close. And, considering the fact that you'll be going to the theater at Boscobel that night, staying in that area overnight makes sense. So, keeping your current overnight plans makes sense.
PS: Boscobel is a magnificent setting for enjoying the theater. Get there earlier enough to enjoy the magnificent views of the Hudson River, among the best anywhere.
As for seafood restaurants in Tarrytown, there's not much to choose from. Striped Bass is okay, nothing great, but decent. It's right on the river. O

You can bring a picnic dinner to Boscobel to enjoy the grounds and views before the show. I see from the website you can do the same this season. In the past I've just packed my own from home, but a deli anywhere can pack you some sandwiches and salads to go. They're ubiquitous here in the north east - every strip mall has one, as does just about every gas station.