Vacation House

Here's a comprehensive list. Only question is how far you want to go.

https://en.m.wikipedia.org/wiki/List_of_summer_colonies#United_States

That wiki list is quite weird in terms of the towns included

I am a Hudson Valley person; that decision was dictated partly by the nature of my work -- I can't be three hours out of the City if a client calls -- and partly by my budget. But I also have many happy memories of having a house at the beach in Nassau County.

Start with "what do you want to do on weekends?" and add in "how much time are you willing to spend getting there?" The third question is probably "do you want to be near many of your friends?" (There's a pretty well-worn track from some parts of Brooklyn to the North Fork, for example.) The fourth consideration would be, "who's going to take care of the property?" Nothing is turn-key; prepare to spend some of your time hanging out with the plumber/exterminator/landscaper.

I can't imagine paying Manhattan prices only to spend my free time somewhere else. Seems like a huge waste. But that's me.

+1 to front_porch's advice.

Once you've answered those questions, consider renting in those locations for a few months -- See if you really want to be there in different seasons, weather, and moods. Also to understand what those communities are really like: outposts of Manhattan with lots of weekenders (or bitter escapees), or residents who don't really like 'downstaters'. Also, if you have kids, consider whether they really want to be away from their friends/activities on the weekends, or how much you will have to be a hotelier to all their friends.

If you're interested in airbnb'ing the place, then it will never really be 'yours', in that way that you can easily walk away on Sunday evening and leave the vacuuming and the dishes in the drainer till the next visit. You're essentially sharing a home with others, with the attendant responsiblities (and the airbnb'ers have no responsibilities, so it's all on you).

I would add: don't believe broker listings when they claim 'only 2 hrs from Manhattan'. Drive it yourself a few times in a variety of situations (Thursday and Friday of holiday weekends).

That said, I've had a 2nd home 3-1/2 hrs outside of NYC for 20 years, and love it. It's been far more expense (renovations, maintenace, things you don't have time for like lawnmowing and snowplowing, not to mention the cost of owning & garaging a car in NYC) than I imagined, along with myriad challenges (left X in one place, and now have to do without for a week or two) but I've made good local friends, met New Yorkers I never would have met in the city, and have closets and cupboards to store everything that doesn't fit in the city apartment.

A friend of mine is very big on Easton.

@stache - what state is Easton your friend likes in? I see a few on the map in various states.

@richardberg completely agree. For years I practically did not leave the island, except as required for work. But having spent a weekend in a house near a lake this past COVID summer (instead of anything more exciting), I realized how nice it would be to be able to get away sometimes.

I've really enjoyed utilizing Airbnb, home away over the years to explore new places. I did own a couple of small vacation cabins in the Northern Catskills near Cobleskill. One that I built myself on 10 acres, and another that I renovated on a very tiny lake called Bear gulch lake in a town called Jefferson. These were very remote areas back then, and for the most part still are, and that's what I liked about them. The homes were relatively inexpensive to build/purchase as well as maintain. So if I didn't use them for a few months it didn't bother me...

I recently, briefly considered buying a place up near old Chatham New York. The areas getting pretty popular, so slightly more services available. Some friends own a yoga retreat up there.

I believe the Easton that most New Yorkers have vacation homes in is Easton, PA. I would second that recommendation — it is a lovely, low key little town, a little over an hour’s drive out of Lower Manhattan.

(1) You need to decide whether this is a "vacation home," or a "weekend home." If you have an office job (or at least one that hopefully will be an office job by next summer), a house 3 hours away is not, at least in my view, a weekend home.
(2) While people often disparage the places NYC folks flock to for second homes--and there is a fair amount of truth to the irony of buying a second home surrounded by the same people you left--it is dramatically easier to remotely own a home in places with infrastructure to support second homeowners. Are the supermarkets open at 9:30 pm on a Friday when you arrive? Is there a decent restaurant to be found? Butcher? Fish store? Depending on your budget, property manager? E.G., many of our service providers (plumbers, oil company, landscapers, pool company, etc) keep keys or access codes to our house or garage, and work while we are away. The flip side of this is that, if you want a "vacation house" to rent, you probably will be better off where there is infrastructure for short-term rentals (i.e., agents who will open and close house, check for damage, arrange cleaning, etc). Perhaps the Jersey Shore.
(3) As others have noted, renting your house is a vastly different equation. That is a vacation house, not a second home. My wife and I joke every time we buy something new that we need to buy two of them, one for each house. Back when there was business travel, probably once a month or more I took a taxi from the airport straight to our house, where there is a second car in the garage. Just about as often, my wife would drop me at the airport on the way back to the city on Sunday. Opening and closing the house every time you arrive or leave to make it your house or a guest house is a very different experience. A good friend moved to Los Angeles 10 years ago but kept his house in Quogue. He still doesn't rent it or let anyone else use it.
(4) I suggest that you do an extended rental before buying to test your resolve. Not a few weeks or even summer rental. 6-8-12 months. See how much you use it, particularly in colder months, when school is in session if you have kids, etc.

Yes, Easton PA. Apparently this is a growing area with upward pricing prospects.

Surprised to hear that about Easton, although I haven't been up there in a number of years since my grandparents passed. They lived just on the other side of the bridge in New Jersey. Easton, the little city itself had the air of a riverfront town that had seen better days. Though certainly some of the country surrounding the city was pretty enough. Glad to hear people saying good things about it.

Looked for rentals in Easton, PA on VRBO.. not too many choices, unless I significantly expand the search area. Maybe it is not the season. Thanks for all the suggestions!

"That wiki list is quite weird in terms of the towns included"
Agreed nycSport

And after the general mention of "The hamptons" which then goes on to list nearly all individual hampton towns except East Hampton, quite apropos, a town certainly last on my list out there.
Though no mention of the North Fork, a glaring omission.

While I have no experience with Connecticut, there must be numerous towns on the sound worthy of a mention.

Pennsylvania as well. So many numerous Pocono mountain resort towns, this list is quite deficient.
And my own 2 honorable mentions not necessarily for having a vacation home but just for visiting, Amish country and a darling little town called New Hope.

Lake Lanier in Georgia.