With a baby? Just visit relatives...

Hotel in Rehoboth for two nights

PP. On a recent NYC trip, we walked the High Line park trail to see what the fuss is about. There's a gourmet market about halfway in. Chinatown is also a good place to look around and eat.

Many cities have free "Greeter" programs if you arrange well in advance. Then you can get a private walking tour that won't be impacted unduly by a fussy baby.

Annapolis

NYC (with a bargain hotel - esp. near Labor Day)
Chicago
Nashville
New Orleans
Quebec
Montreal

Anything with museums, restaurants, harbor cruises, outdoor landmarks, and free concerts/festivals where babies can come and go.

Museum restaurants are often pleasant, relatively cheap, and baby friendly.

If you love theater...try switching off the baby and one parent goes to a matinee and the other goes to the evening show.

Some NYC things I did with an 8 mo infant...MOMA Target Free Thursday Eve and cafe dinner; free Fashion Institute of Tech museum to see a special exhibit; stroll Greenwich Village and go to baby stores, cupcake at Magnolia bakery, visit playgrounds; free Staten Island ferry harbor ride. We had a toddler on this trip also.

My baby loudly hated car seats and being restrained in any way, so Amtrak was a savior. Perfectly happy on the train. New York, Philly, Vermont, Charleston, Boston Richmond, all great trips.

Though to be honest, DC tourism was maybe the best because it didn't feel like a waste if the baby got fussy and I had to leave a museum earlier than desired, since it was free entrance.

Philly.

Pittsburgh

Hilton Quebec City is in a great location, very walkable. Get a high floor/parliament view if you can. Quebec City is super cheap, awesome food.

Favorite inexpensive trips? Ways to explore with baby that don't cost that much. Plus if you have a fav Hilton property in a fun city? We have tons of Hilton points.

Looking to take drivable trips and open to flying on points too