The Picture-Perfect Hudson Valley A-Frame Airbnb I'll Never Stop Recommending

Smack in the middle of summer, on a prime July weekend when New York City was serving up its usual cocktail of packed sidewalks, nonstop bustle, and a humidity level that felt borderline personal, I knew I needed out. Upstate New York has no shortage of escape routes—charming inns, boutique hotels, and endless Airbnb gems—and choosing one is always the hardest part. Even as a lifelong New Yorker, I’m constantly discovering new corners of the Hudson Valley.This time, I wasn’t looking for just a change of scenery; I needed to be fully engulfed by nature. I wanted morning coffee among the trees, a reason to put on hiking shoes, and a weekend that involved a little less screen time and a lot more touching grass. After one of my favorite pastimes—falling down the Airbnb search rabbit hole, of course—my partner and I found ourselves heading to “The Upstate A,” a recently renovated, über-restorative A-frame cabin in Pine Plains that felt like exactly the reset we were searching for.The second we left the city behind, I felt my shoulders drop. City slickers will know the feeling—the kind of exhale you only get when you trade honking cars for wide, open roads. Just over two hours from Manhattan by car, we made our way to Pine Plains, a charming and ultra-scenic Hudson Valley town tucked right along the border of Dutchess and Columbia counties. (If you’re coming without wheels, take the train to Rhinecliff station and grab a rideshare from there.)While two people don’t exactly need a three-bedroom cabin, my longtime craving for extra space after nearly a decade of compact NYC living made the decision feel easy. There’s something undeniably relieving about having the proper amount of room to spread out, especially when the space comes with a forest as your backyard.Directly after the highway's exit, we were greeted by long stretches of farms and rolling hills. Eventually, the winding street on which the A-frame resides came into view. Located on a quiet acre of land with seemingly endless woods behind it, the cabin appeared just as it did in its pictures: Its wood panels complemented the darker roof, and the front facade was made almost entirely of glass. The house was built back in 1968 but was renovated and redesigned in 2021.All three bedrooms and both full bathrooms are located on the first floor, alongside a washer and dryer. Upstairs, we found the living room with its massive glass windows and attached balcony, perfect for taking in the forest views. Across from it sat the dining table, and to the right was the spacious, modern kitchen with its high-tech amenities (and a gifted bottle of wine). A spiral staircase from the kitchen led to a private loft that could be used as a fourth bedroom.We quickly realized that this wasn’t your typical “cabin in the woods.” It was there—alongside the spanning, triangular, floor-to-ceiling windows under the 20-foot ceiling—where I truly appreciated the thoughtful layout of the space. Within these open, airy common spaces, I understood how this A-frame could comfortably host up to eight.Before we really settled in, I wanted to catch my bearings with Pine Plains. I hadn’t spent much time in the town other than a quick drive through it. Thanks to a recommendation from the hosts, we drove five minutes to Chaseholm Farm, an adorable farm store that sells local produce and goodies (like Alleyway Ice Cream made in Saugerties, another Hudson Valley town). It was sunset, and the sparkly outdoor lights were just turning on as we parked. On our way out, I rolled my windows down for the quick drive back, taking in the fresh air.For dinner, we went to one of my nearby favorites, Stissing House. It's one of the oldest taverns in America, and now a hotspot with intimate dining rooms and fireside lounges. A white colonial building with a beloved light green door, the restaurant was buzzy and dimly lit. After dessert (and the perfect summer martini—Ketel One vodka with an orange twist), I was more than happy to head back to my ever-so-comfy bed.While we slept in the primary bedroom with its sleek, teal-tiled wall bathroom (and eucalyptus shower spray), I wouldn’t mind resting my head in any of the rooms—all featuring bright pops of color, cozy linens, and inviting house plants. The next morning I headed upstairs to the living room, now engulfed in sunlight that poured through the green canopies. I made a cup of coffee (beans were provided by the host) and enjoyed it while sitting on the balcony, accompanied by birds singing sweet summer songs. Before we left for a bracing hike up Stissing Mountain, I took a quick peek at the outdoor firepit alongside the forest.A peek of the A-frame's backyard, where there's a firepit, barbecue, and dining table Jessica ChapelA short drive away, the Stissing Mountain fire tower will lead you to views, views, views Jessica ChapelThe steep uphill trail that we took led to the Stissing Mountain fire tower. Admittedly, I was a bit winded from the trek—but once at the top, looking out at crystal lakes and bright green hills that seemed to roll on forever, I was in awe. I reflected on the considerable contrast to my Brooklyn apartment view (or lack thereof) in Williamsburg, where I can no longer see the open waterfront and NYC skyline thanks to new building developments. Gratitude for the moment, the stillness, and the vastness washed over me.After a lovely final hurrah dinner at nearby Oakhurst Diner, an old-school joint with finger-licking bites, we spent a final cozy night in the picturesque cabin before it was time to be on our way. I left the A-frame feeling more grounded than ever—and (maybe naively) prepared to handle another summer, both with my partner and the toxic love of my life: NYC.More of the host's properties:While this A-frame has been the hosts' show-stopper for quite some time, I recommend looking into their new, also-idyllic properties in the nearby town of Red Hook: The blue cabin and the green cabin. Both have stellar amenities, space, and sit next to one another on a babbling creek. (You can also book both properties for bigger group stays and events on the joint listing page.)Other Airbnbs I considered nearby:Chic modern barn stayThis gem, dubbed the “Stissing Mountain Cottage,” is a newly built and voluminous barn-style retreat minutes from upstate’s most iconic restaurant and the weekend polo scene. Best for bigger groups or families, it fits up to six guests in its three bedrooms, and is perfectly positioned in a scenic wooded area. It's also close to the quaint town of Rhinebeck, with a main street of shops and restaurants to round out your itinerary.Cozy lakeside escapeFor a larger group stay in Pine Plains, this quaint base just might have it all. With five bedrooms and rustic decor, it doesn't quite get more “upstate countryside” than this. It's filled with color—from the pale green cabinets in the kitchen to the inn-inspired wallpaper in the bedrooms. Your group can relax in the hot tub, cozy up in the spacious living room, and create memories post-exploring in the light-filled sunroom that overlooks the lake.Iconic private island retreatTucked away on Twin Island Lake, this “private island” stay is somewhat of a local celebrity when it comes to to the local Airbnb scene in Pine Plains. Here, you'll canoe across a lily pad-dotted lake to your own paradise. Inside, a one-bedroom haven sleeps up to four guests (best for small families, as there are two sofa beds to accompany the primary suite). The whole island is yours, but you can stay close to headquarters by taking advantage of your backyard hammock, grill, and dining area.1763 farmhouse on a creekWhether you're looking for a serene getaway in the heart of Pine Plains or an inspiring, redesigned Colonial farmhouse, this home on an idyllic country lane awaits up to four guests in beautiful Dutchess County. Just two hours from New York City (and 35 minutes from Hudson), this group-friendly Airbnb is spacious, comfortable, and amenity-forward. Each of the two cozy bedrooms boasts a queen-sized bed—and one even has a skylight.