262 upper byrdcliff road woodstock ny
262 Upper Byrdcliffe Road, Woodstock: $1800/mo.

Our title today is RTMMYCMDTW — that well-known acronym for rentals that might make you consider moving during the winter. I’ve moved during the winter in four different states: Alaska, California, Michigan and New York (alphabetical order). Needless to say, packing up a moving van on a December day in San Francisco is much more pleasant than unloading a moving van in upstate New York a week later. Alas, nothing to be done. Sometimes, when you gotta move, you gotta move. These days, it would take a lot to convince me to move in the winter. Or in the rain. Or at all. The rentals I found today in the Upstate listings, however, might change my mind about the idea. Maybe. Probably not. Okay, maybe for this one, a 1938 Bauhaus in the artists’ colony…

262 upper byrdcliff road woodstock ny2

See? Cool architect-designed house with an interesting tidbit about it being the sister house to Alistair Cooke’s Hampton abode. Located near Woodstock’s Byrdcliffe arts colony, the rental sits on 14.5 acres just outside of the village of Woodstock. Beautiful interior. Beds: 3. Baths: 2. Square Feet: 2000. Lot Size: 14.5 acres. Distance from Brooklyn: 2.5 hours.

262 upper byrdcliff road woodstock ny3

262 upper byrdcliff road woodstock ny4

262 Upper Byrdcliff Road, Woodstock (Win Morrison) GMAP

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89 hunns lake rd stanford ny
89 Hunns Lake Road, Stanford: $3200/mo.

Can I afford $3,200 a month for rent? No. Not even for a stunning circa-1790 Colonial that comes with nine fireplaces, four acres of land, and a big red barn. But maybe you can. Located in the rural town of Stanford in Dutchess County. And yes, there’s a pool. Beds: 4. Baths: 4.5. Square Feet: 4414. Lot Size: 4.3 acres. Distance from Brooklyn: less than 2 hours.

89 hunns lake rd stanford ny2

89 hunns lake rd stanford ny3

89 Hunns Lake Road, Stanford (Paula Redmond) GMAP

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700 zena rd woodstock ny
700 Zena Road, Woodstock: $2290/mo.

Another architectural beauty in Woodstock, this one is on the Sawkill Creek in one of the prettiest areas in all of Ulster County (dare we say all of the Catskills?). The two-bedroom, two-bath modern cottage was featured on the cover of Abitare Magazine. If you love yourself some glass walls, you’re going to fancy this one. We sure do. Beds: 2. Baths: 2. Square Feet: 803. Lot Size: 3 acres. Distance from Brooklyn: 2 hours.

700 zena rd woodstock ny2

700 zena rd woodstock ny3

700 Zena Road, Woodstock (HH Hill Realty) GMAP

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696 gentile rd stephentown ny
696 Gentile Road, Stephentown: $2000/mo.

Nothing modern here. Just an old-fashioned 19th century farmhouse on eight-plus acres in Columbia County. Includes a wood stove, high ceilings, and plenty of light. There’s not much around this part of the area except trees, lakes and beautiful houses. Feels remote. Beds: 2. Baths: 2. Square Feet: 1876. Lot Size: 8.3 acres. Distance from Brooklyn: less than 3 hours.

696 gentile rd stephentown ny2

696 gentile rd stephentown ny3

696 Gentile Road, Stephentown (VantagePoint Realty) GMAP

* Rentals That Might Make You Consider Moving During the Winter


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