RECENTLY IT DAWNED ON ME that the way to live or spend time here on the East End of Long Island for (relatively) cheap is to rent year-round. For $2,500/month, less than many a New York City apartment, you can have a 4BR 2 bath Colonial cutie on a lot full of mature trees in Southampton village.
Rentals out here are even cheaper if you take them for fall, winter, and spring only, leaving the two high-season months for the landlord to maximize his/her annual income. Houses that command $5-6,000 or more per month in July and August are more like $1,500-$2,000/month in the off-season, plus utilities.
The pluses are many: no crowds, no traffic, still gorgeous weather in spring and fall. Many people say they love winter out here for its tranquil beauty. If there’s a fireplace, so much the better.
Just a thought.
casaCARA 
But “ugh”. How could you live in what amounts to a time-share…on top of that, one where you are attached to the furnishings for 9-10 months out of the year. I guess it’d be a strategy if you run to the Berkshires, Cali, or France for two months in the summer (or further afield AND don’t care about the furnishings, kitchen stuff), but yick…I guess you’d have to put all your own things in storage when you move out in May to have uncouth rabble knocking around in the place for summer.
We almost rented a place in France that had a similar stipulation but in our case, it was the owner who wanted to come to the house for two months in the year (off-season but very inconvenient for us nonetheless). We ended up pulling out of the deal.
That house you photographed is cute as hell though.
Brooklyn Beckons…
Well, one can rent for the full year then and get the two summer months included, without paying a premium for those. There are plenty of such opportunities around.
Love the old houses up there in the Hamptons and I’m glad to find your blog! Have a great trip to Maine!
Have you ever looked much into off season weekly beach house rentals?
Not weekly. But I know you can get a little 1BR cottage near Maidstone, a beautiful beach on Gardiner’s Bay in Springs, in the off-season for $1,000/month. You can’t beat that. I’ve seen them on Craigslist.