How the Owners of a Charming A-Frame Airbnb Put Pine Plains on the Map
The Upstate A, a rare architectural gem, in Pine Plains, NY. Photo: Derek Walker.
During the middle of the COVID-19 pandemic, Rebecca O’Neill and Adam Ecker found themselves seeking respite from the city in a cozy Airbnb in Woodstock, New York. Upon happenstance, they discovered their dream country property was for sale a few towns over. Before the vacation was over, they had put in an offer on the property and were already dreaming of how to convert an outdated 1968 A-frame into the perfect Airbnb.
After a full year of renovations, The Upstate A opened its doors to guests and has continued to draw the crowds to the quaint town of Pine Plains for some serious R&R. From utilizing the power of Instagram, to do’s and don’ts during a reno, the couple opens up on how you can make your Airbnb the next small town hotspot.
How did you find your Airbnb rental property?
For years we had talked about purchasing a home in the Hudson Valley region – we frequently visited the area, staying in others’ Airbnb’s and dreaming of having one of our own someday. In early April 2020 we were actually renting an Airbnb near Woodstock when my husband (a regular Zillow browser) stumbled upon a listing in Dutchess County.
It was an A-frame – a rare architectural gem, but it needed a ton of work, which admittedly was a bit nerve-wracking in those early pandemic days. But we immediately started envisioning how we could transform it into something unique and gorgeous, which ultimately overpowered our pandemic and market-related anxieties. We got in touch with the broker, drove right over and toured it...and the rest, as they say, is history.
What propelled you to want to become a host?
We have had such positive experiences staying in Airbnb’s over the years and all over the world. We wanted to be able to “pay it forward” in a sense and bring the same wonderful times we’ve had to others.
Tell us about The Upstate A! What will guests love specifically about your property?
The Upstate A is a three bedroom, plus sleeping loft, two and a half bathroom A-frame set on a quiet cul-de-sac in the heart of the Hudson Valley. Built in 1968, it was fully renovated by us in 2020-2021. It is a truly magical place that we have poured our hearts and souls into – and I think guests can really feel that when they spend time there.
We pride ourselves on the aesthetics and design of the house – our overall look and feel, the furniture, the art, the plants – and we think guests appreciate it, too. And of course, our main room – which we have affectionately dubbed “The Great Room” – is a total show-stopper. It’s the peak of the “A” with soaring 20-foot ceilings and a wall of windows and glass overlooking the surrounding trees. It’s impossible to feel anything but relaxed in that room, especially if you’re someone used to the hustle and bustle of urban life, like us.
Reach peak relaxation in The Upstate A’s stunning Great Room. Photo: Derek Walker.
As a host, what do you think sets you apart from the rest?
When we were planning this house, we were able to draw upon our experiences with other Airbnbs we stayed in over the years – learning from the good, the bad, what we liked and didn’t like. With that in mind, everything in our house was created with an incredible level of intent; everything is fully oriented toward ensuring our guests have a totally relaxing, pleasant and gratifying stay. And of course, the A-frame design — certainly not common these days — makes our abode quite unique from other offerings on Airbnb.
What's one tip you could share on how to become a highly successful Airbnb host?
Sharing the renovation journey on Instagram really helped us generate excitement about our Airbnb before it was even available to book. And now for a shameless plug: you can check us out on Instagram at @upstate_aframe.
Any funny stories or mistakes you can share from running your rental?
Most of our “mistakes” were related to the renovation itself – like not anticipating that everything takes longer than you think it will, especially in this supply-chain-strain, contractor-shortage environment. That said, I think the lessons learned from our reno can be applied to prepping your house for Airbnb in general, namely: make sure you build in a longer runway than you think you need to scale everything up.
The fully renovated home has 3 bedrooms and a sleeping loft. Photo: Derek Walker.
How would you describe your perfect vacation experience?
Days jam-packed with adventure and beauty, gastronomical exploration, lots of wine, and importantly, a serene, beautiful home to come back to at the end of the day.
What are your must see and do’s in the Hudson Valley area?
The Hudson Valley is teeming with activities, delicious food and dazzling beauty. When we are up there, hiking as much as possible is an absolute must. Some of the best hikes in the region are Stissing Mountain (2 miles from our house), Mount Beacon, Poets’ Walk in Rhinebeck and Woodstock’s Overlook Mountain.
Some of our favorite places to eat & drink are Dutch’s Spirits (just down the road from us), the newly opened Champetre in Pine Plains, Cinnamon, Market St and Aba’s Falafel in Rhinebeck, and Oakhurst Diner, The Dig and 52 Main in Millerton. There are also incredible vintage and antique stores all over our corner of the Hudson Valley — especially in Pine Plains (where our house is located) and nearby Hudson, Rhinebeck and Millerton.
Experience the magic of The Upstate A for yourself and book your next getaway on their Airbnb page. You can read more host stories for additional inspiration on making your short-term rental the top pick for guests.