DH and I have never been to New England and are thinking about going for a long weekend after Labor Day. We want to go somewhere that is easy to get to from Chicago. We would like to do some driving/exploring but don't want to be in the car for hours. We thought we would fly into Manchester. We had heard Portsmouth was nice but a few people said we should stay further north, like Ogunquit because it is more scenic. We would mostly like to drive along the coast and see the sites, walk around the town, maybe take a boat ride. I would like to get input on which location might be better for us and input on lodging. We would prefer something on/near that is reasonably priced (<$200). Thanks!

Maine!! I love the Inn by the Sea in Cape Elizabeth; its not far from Portland- about 12 miles and that is a fantasic place to visit. I miss it terribly... as my little 7 yr old twin niece and nephew are there as well as my 5 yr old nephew... Also another great place is the Cape Arundel inn in Kennebunkport... right across the street from the Bush's estate!

Potsmouth is a nice town -- but I would definitely stay in Ogunquit - but definitely visit Portsmouth.
Ogunquit seem to be exactly what you're looking for - a nice town you can walk around -- many restaurants - a cove where you can take a boat ride and a beautiful walk along the ocean...
As far as places to stay there are many nice places - Terrace by the Sea is a motel/inn type - Beachmere is a big old inn converted into motel type rooms -- right on the Marginal Way (which is the walk I mentioned) - There are many more motels -- depending on what you're looking for - many do not have pools so if you mention exactly what you're looking for it would be easier to recommend....

Most definately Ogunquit!!!

Ogunquit & Portsmouth are apples and oranges - completely different. Portsmouth is a small, very old seaport city. Some very good restaurants, interesting streets and waterfront area, and a very nice restored historical village (Strawberry Banke).
Ogunquit is an artsy resort town on the nicest stretch of beach on the Maine coast. Lots of galleries, shops, and restaurants. The good news is they are about 40 minutes apart, so you can easily explore both, even on a short trip. After labor day, you should have no problem finding someplace < $200.

If you can get a room at the Wentworth By The Sea (Marriott), in New Castle, NH, it's a beautiful hotel and it's just outside of Portsmouth, easy access to both Ogunquit and Portsmouth. Rooms book up fast, so if you can't get one, I'd agree with the other posters and say Ogunquit. We've stayed several times at the Anchorage By The Sea there and it's right on the Marginal Way on the ocean. Has a few outdoor, and an indoor pool, huge outdoor hot tub, sauna, and their property across the street has rooms with king beds, gas fireplaces and 2-person jacuzzi tubs.

Thanks for your help. I am definetly going to do more research on Ogunquit and check out these hotels.

Can you walk into town from the Beachmere or Anchorage by the Sea?

the inn by the sea in cape elizabeth is right on the beach... check out their web site.

It is about a half a mile walk to town from both the Beachmere and the Anchorage. The ocean walk along the Maginal Way to Perkins Cove is about 1.5 miles.