Why book?
This cozy getaway is designed for vintage lovers and hygge seekers—and is almost guaranteed to make it onto your Instagram feed. Tucked deeper into nature than its older sibling in Windham, Eastwind Oliverea Valley derives its special sauce fromits harmony with its surroundings, complementing rather than taking away from the landscape.Its woodfire-warmed lounge, sauna, and proximity to ski slopes make for ideal wintertime companions, but come summer a pool, outdoor yoga, and even DJ sets will draw the crowds. A small but excellent seasonal food menu and co*cktail list round out its offerings.
Set the scene
While it welcomes kids, Eastwind is designed for (self-sufficient) adults, so don’t expect a full roster of activities. We saw chic and active city couples dressed in Patagonia and heavy knits return from winter walks to unwind in the lounge, where a crackling wood fire and tunes from the likes of Phoenix and MGMT keep company. This central area—a combined lounge, restaurant and a bar—is the property’s nerve center. Its vintage decor, a warm pastiche of texture, wood, and print, beckons you to get comfy with a book by day or a locally made brew by dusk. At night, s’more kits lead guests back out to the fire pit, where blankets and a spread of stars await.
The backstory
Eastwind Oliverea is the group’s first ground-up build, but in the early 1900s, the property was once home to the McKenley Farm, a popular seasonal vacation spot for African American families. Many years later, it also served as a site for the Appalachian Mountain Club and then the Shangri La at Mountain Gate hotel. “We were drawn to this location as the topography sits way back in a natural bowl-shape. We were excited to be able to tuck our cabins into the hillside and offer picturesque views from every room,” Bjorn Boyer, Eastwind’s co-founder explained to me. It isn’t just the brand’s trademark A-frame cabins that have been carried over to this property. As with the others, Bjorn and wife and creative director Julija’s thoughtful touches are everywhere, from the singular pieces of vintage decor that fill the rooms to the economical (and ecological) construction of the cabins.
The rooms
Accommodation here is a combination of 27 freestanding cabins and cabin suites as well as rooms in a central guesthouse. We stayed in a 400-square-foot Lushna suite that came with a living space, a wooden deck, a bathroom with a green tiled-shower, and a deck on the ground floor. Up a set of “stairs” made from wooden crates, a loft with a bed that's pushed up against a large window and was perfect for curling up and watching the snow (but a squeeze for my tall husband). Going up and down requires some athleticism, especially at night, so grab a regular room or suite if you have shaky knees. The standard cabins are smaller and just as pretty, but have outdoor showers. While no two cabins are alike, they’re all bound in aesthetic by a Scandinavian minimalism and earthy tones. Little touches include a selection of books focused on native flora and fauna and art depicting local landscapes. The Upper Valley King room starts at $299 per night; Lushna Cabins at $359.
Food and drink
Dandelion, the property’s restaurant and bar, is inspired by cozy aprés-ski bars, its hearth and warm corners designed to offer shelter and retreat. The menu, consisting of “international comfort food,” is small, thoughtful, and impeccably executed by Daniel Cipriani, the co-founder and F&B director. I practically inhaled the Thai-style coconut cream soup I ordered for dinner (my husband reacted similarly to the dry-aged pork chops). The co*cktails are similarly impressive—over my stay I sampled both the Paloma and the gin-based Foghorn. The other standout was the breakfast basket that gets delivered like clockwork to your room each morning, including fresh pastries, muesli, fruit, yogurt, eggs, coffee, and juice. True to the hotel’s philosophy of repose and rest, the basket invites you to linger longer in your rooms, with enough to keep munching on through the morning. A word to the wise: bring snacks on your stay as Dandelion is only open for dinner. For a change of pace, crowd-favorite Phoenicia Diner is a 15-minute drive away.
The spa
While Eastwind doesn’t have a spa, it does have two saunas housed in barrel-shaped cabins—one of which is an infrared sauna. Like with all its accommodations, the saunas come with picture windows.
The neighborhood/area
Big Indian isn’t Woodstock. It’s not even Phoenicia. It’s small and tucked away. That’s one of the best things about the location: the sense that you’re further away from things than you really are, and that makes it the perfect place to settle in and hunker down. But if being sedentary isn’t your thing, the McKenley Hollow Trailhead starts at the property line and there are several other great hikes (the Hunter Mountain Trailhead, for instance) and attractions (West Kill Brewery) within driving distance. One afternoon, we hiked up a short trail, another day we drove to Woodstock for lunch, but the rest of the time we lazed about, chatting and reading—or doing absolutely nothing at all.
The service
Bjorn commandeers a small team, and often doubles up as bartender, concierge, and sauna turn-oner. On the morning of our departure, I opened the drapes to find the property blanketed in snow. Despite that, our breakfast basket arrived not a second too late, with the pastries still warm. As I poured myself coffee, I watched a tiny team get to work, plowing paths through the snow. Bjorn himself was stationed at the guest car park, digging out every single car and clearing them of snow. By the time we hauled our luggage over, our car was practically squeaky clean. We certainly weren’t expecting it, but more than appreciated the kindness.
Eco effort
The design at Eastwind is purposefully low-impact, whether it’s the sustainable, renewable Larch that’s used in the construction of the cabins or the repurposed vintage decor and furnishings. Notably, most ingredients used in Dandelion’s menu are locally grown, foraged, and sourced.
Accessibility
The bar and common areas are ADA Accessible, as are a few of the king rooms.
