Wylder Windham Is a Mountainside Escape in the Hudson Valley

With a prime location near Hunter and Windham Mountains, Wylder delights with creekside views and top-tier dining.

For outdoor adventurers in the Hudson Valley, nothing hits the spot quite like an escape to the mountains. Throughout the year, peaks like Hunter and Windham tempt locals and visitors alike with everything from hiking and mountain biking in summer to skiing and snowboarding in winter. Of course, activities are only part of the story. While the to-dos may inspire a visit, the overnight accommodations keep people coming back for more.


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At Wylder Windham, it’s all about the experience. With an idyllic location next-door to Windham Mountain and a short drive away from Hunter Mountain, Wylder Windham is a top choice for overnight guests in Greene County.

Wylder Windham
Photo by Sabrina Sucato

“Windham was chosen for its nostalgia, proximity to major cities like New York (90-minute drive), and experiences/offerings nearby, including Windham Mountain and Windham Country Club,” explains John Flannigan, owner and founder of the Wylder brand, which also boasts a location on Tilghman Island, MD. “Located on 20 acres of land, with the Batavia Kill running through it, Wylder Windham is one of the biggest boutique properties in the area, offering plenty of accommodations, onsite activities, meeting and event spaces, and more for the perfect leisure getaway.”

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For repeat visitors to the mountainside region, Wylder’s location may seem familiar. That’s because its previous incarnation was The Thompson House, a property which was thoughtfully restored to create a destination that today spans multiple buildings to create a one-of-a-kind resort experience in the Hudson Valley.

Pickleball courts
The pickleball courts. Photo by Sabrina Sucato

When it came to the site’s redevelopment, one of the main goals was to honor the architectural integrity of the existing seven structures, notes Flannigan. Instead of tearing them down, the Wylder team opted to make major structural improvements to some buildings and complete makeovers to others. Throughout the process, they worked to integrate sustainable elements, including an overhauled HVAC system, energy-efficient windows, and new clapboard siding. They also removed dead trees and overgrown shrubs to help avoid rot to the property.

All in all, construction took 12 months. During that time, the interiors received brand-new oak floors, shiplap walls, and wood moldings. The overall effect is a down-to-earth atmosphere that perfectly complements the property’s breathtaking surroundings. Even the bathrooms feel inspiring, thanks to elegant white tile and luxurious Carrara marble.

Wylder Windham bedroom
Photo by Sabrina Sucato

What to Expect at Wylder Windham

“The Wylder brand focuses on iconic, soulful properties and wide-open spaces designed to get guests out of the rooms and embrace the timeless pleasures that the surrounding land has to offer,” Flannigan explains. Such a concept fits perfectly in Windham, a town known just as much for its skiing and snowboarding community as for its hiking and biking adventures, not to mention the ample leaf-peeping opportunities.

Because the hotel spans seven properties, comprised of lodges, inns, manors, and cottages, no two stays here are the same. Visitors can pick and choose between The Pines Inn (28 rooms), The Tamarack Lodge (16 rooms), The Manor (14 rooms), The Spruce Cottage (14 rooms), The Evergreen Lodge (25 rooms), The Main Lodge (13 rooms), and the Farmhouse (1 key residence). Each building boasts a unique personality, thanks to a design by Brooklyn-based design firm Post Company and architect Jason Anderson, and construction by Baxter Built. In total, there are 110 suites and king- and queen-sized rooms for guests to unwind. Depending on which room guests book, they can look forward to everything from oversized balconies (in 82 rooms) and views of Windham Mountain or the Batavia Kill. For those who want to go big, The Baller Suite features double balconies that overlook the pool and the mountain beyond.

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The Lodge
Photo by Sabrina Sucato

Things to Do

As far as amenities go, perhaps it’s easier to list what’s not at Wylder Windham than what is. Not only does the dog-friendly property boast 20 pastoral acres for guests to explore, but it also tempts with a heated pool, electric bikes, hammocks, fire pits, tubing, tree swings, wood-fired saunas, a hot tub, a dog run, lawn games, pickleball courts, and a dedicated game room complete with vintage arcade games and shuffleboard, as well as a pool table and foosball. For anyone who stays on Fridays, the s’mores nights are a must. And on Saturdays and Sundays, aspiring at-home bartenders won’t want to skip out on the cocktail-making classes, during which guests can learn how to make seasonal libations.

And that’s just on the grounds. Very close by the property are the Windham Path, ideal for walkers and runners, and the Windham Country Club, an 18-hole public golf course that sits adjacent to the hotel. Plus, did we mention that Windham Ski Mountain is only a two-minute drive away? For easy access, guests can book the restored vintage Land Rover Defender for complimentary transportation to and from the mountain. A shuttle to area businesses such as The Vineyard at Windham and Windham Fine Arts is also available, and the town center is only a 30-minute walk away.

The Wyld Pass

There’s a ton to do at Wylder Windham, and the hotel knows it. That’s why it’s excited to add the Wyld Pass to its lineup of offerings in 2024. Aimed at locals who want to tap into the amenities available on the grounds, the pass allows non-hotel guests to make use of the oversized heated in-ground pool, pickleball courts, wood-fired saunas, recreation room with vintage arcade games, dog run and yard, and The Pine lobby (and free Wi-Fi). On top of that, passholders can take 15 percent off the best available rate and food and beverage at the hotel.

The Wyld Pass will be valid from Sunday to Friday from April 1 to November 1 and costs $1,800 per person for the season. To make the deal even sweeter, three additional guests are allowed per visit.

That being said, the Wyld Pass is available in limited quantities to ensure the hotel can continue to deliver a quality experience to guests. Anyone interested should email guestservicesww@wylderhotels.com by March 25 for an application.

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Dining at Wylder Windham

When the hunger pangs hit, Wylder Windham is a one-stop shop for dining as well. The hotel plays host to Babblers, a restaurant that walks the line between comfort food and fine dining. The atmosphere is warm and welcoming, and live music on select days adds to the air of conviviality. Diners can choose between entrees like Sunday Everyday Pasta Bolognese, which features a slow-braised beef ragu, or a butternut squash risotto with toasted pepitas and cinnamon creme fraiche.

The cocktails are worth a mention as well, with seasonal sips like an apple butter Old Fashioned with Woodford Reserve, apple butter, cider, lemon, and orange bitters designed to help diners unwind and cheers to their getaway. Pro tip: Stop by Babblers on Wednesdays and Thursdays for all-day happy hour to kick the pre-weekend festivities off right.

Babblers at Wylder Windham
Breakfast at Babblers. Photo by Sabrina Sucato

In the mornings, guests can visit Babblers Bakery, located adjacent to the restaurant, to savor everything from fresh croissants and pies to coffee and lattes. On Sundays, the restaurant’s weekend brunch dishes up a more lavish spread for anyone in the mood for a hearty start to their a.m. Lemon ricotta pancakes or sausage and biscuits, anyone?

With all the buildings on the property renovated and open for guests, Wylder Windham is ready for an eventful spring and summer season in the Hudson Valley. Looking ahead, the hotel is excited to create even more one-of-a-kind offerings for visitors. First up: Starting on March 24, the hotel will bring back its weekly pickleball lessons led by local pickleball instructor and USTA Certified Tennis Umpire, Cathy Forstl. And, with the new Wyld Pass in play, both locals and guests can keep an eye out for the latest and greatest from the Hudson Valley destination.

“Wylder Windham’s weekly programming will continue to expand with new offerings for our guests, including pop-up events, hosted fireside chats, live music, children’s activities, local tastings, and more,” Flannigan enthuses.

In other words, doesn’t it seem like a Hudson Valley getaway is in order?

Wylder Windham
19 NY-296, Windham

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