@Angelo ProtoSome of the top vacation markets I hear about often are:-Pocono Mountains of Pennsylvania-Catskills and upstate NY-Tennessee - Gatlinburg and Pigeon Forge-Shenandoah Virginia-Blue Mountain region of Georgia-Many Florida marketsIf proximity to home are important, the top two may be of benefit to you.

I know Catskill is up and coming and there are great deals in Kingston and Saugerties too.  

Your best bet from what you said, for proximity and ease of use and volume of vacationers would like be in the Woodstock area or the Catskills.

And later on, take advantage of the 1.1 acres and put up Yurt/ Dome / Tiny house etc as a glamping setup.Pictures:The 3d model Front view ( The barn with loft)Right view (Barn, Kitchen and .. the back part I lovingly call, the pizza) == also, what i plan to do with it.back view ...Current view and the Planned renovation viewThe left side view Location:115 miles from NYC ( 140 minutes)12 miles from Woodstock and Hunter ski mountain. ( 25 mins)8 miles to HITs Saugerties (15 mins)25 minutes to Hudson.The cities I have just mentioned are the TOP Airbnb locations in Hudson Valley/ Catskills as listed below. ( I wrote a scraper program to get all the Airbnb data) city Total number of homes on airbnb Total number_of_reviews average number of reviews Woodstock 141 7720 54.75177305 Hudson 142 6636 46.73239437 Phoenicia 57 3458 60.66666667 Saugerties 125 2983 23.864 New Paltz 66 2237 33.89393939 Beacon 54 1860 34.44444444 Catskill 45 1761 39.13333333 Hunter 79 1445 18.29113924 Rhinebeck 48 1413 29.4375 Kingston 62 1380 22.25806452 Kerhonkson 32 1293 40.40625 Accord 29 1275 43.96551724 High Falls 20 1122 56.1 Tivoli 14 940 67.14285714 Olivebridge 13 886 68.15384615 Rosendale 16 834 52.125 Cold Spring 19 813 42.78947368 Athens 11 803 73 Mount Tremper 23 762 33.13043478 Stone Ridge 17 742 43.64705882 Windham 60 740 12.33333333 Germantown 34 718 21.11764706

Need some help finding some land to build a STR in Upstate (around Catskills ideally) with a budget of $20,000. 

Have you thought about getting a property near a ski resort in the Catskills (Hunter/ Windham)? 

Anyone experience selling/buying in the Catskill Mountains, Upstate NY, ?

Hey I’m new to investor I got a couple of deals in Catskills area first time doing business there any cons or pros 

Decided to buy a SFH in the catskills area near the ski resorts to try and airbnb.

I'm looking in Catskills area to buy a multi as listings are very resonable and great STR returns.