This All-Season Boutique Resort Provides the Ideal Backdrop for a Perfect Upstate Getaway

When the temperatures drop and the crowded streets become slick with snow and sleet, city dwellers know the time has come for a wintry weekend upstate. Just a couple hours away from Manhattan by car or train, travelers will find Windham, a historic town revered for its numerous ski trails, mountainous parks, and trails.

Credit: Michael Carnevale

In this Upper Catskills town, The Thompson House Resort reigned supreme as the premier vacation resort, boasting over 20 acres of expansive grounds and operations dating back to the late 1800s. Following the acquisition of this legendary hotel, Wylder Hotel Windham opened its doors earlier this year as a top-to-bottom reimagination of the beloved former concept, with much aplomb from the next generation of upstate vacationers and locals alike.

Credit: Michael Carnevale

Lodgings are separated into seven different cabins, cottages, inns, and manors around the property. Each of the 110 guest rooms have been thoughtfully and lovingly restored by craftsmen from Baxter Built, and all of their distinct, palpable characteristics have been enhanced in partnership with local architect Jason Anderson and Brooklyn-based design firm Post Company.

Credit: Michael Carnevale

The king- and queen-sized bedrooms feature custom furnishings and oak floors. Sip on coffee or libations while soaking in the fresh mountain air from the comfort of one of the 82 rooms with oversized balconies, which also happen to offer unobstructed views of Windham Mountain or the Batavia Kill. The infamous “Baller Suite” situated at the top of The Main Lodge is the only accommodation endowed with double balconies.

Visitors need not venture far from Wylder, as the possibilities to immerse oneself in nature, even if only for a brief stint, are endless. Dog lovers are able to bring their four-legged friends, as the entire hotel is Fido-friendly; there’s even a dog run. The heated outdoor pool next to The Main Lodge remained open even into late fall, and the pickle ball courts remain open as long as weather permits. To warm up, book a session in one of the wood-fired saunas looking out over the Catskills landscape or Windham Mountain, or take a quick dip in the hot tub. There are also fire pits, and s’mores kits can be snagged at the check-in desk.

Credit: Michael Carnevale

Babblers is the intimate and refined yet approachable restaurant, with seasonal comfort food and local fare galore. The bar and dining room are buzziest through the weekend, and the expansive outdoor dining space is adjacent to the Batavia Kill. In the morning, stop by Babblers Bakery for a cup of joe and a slice of their signature pies; the strawberry rhubarb is phenomenal, but sweets-lovers should opt for the chocolate.

The pastoral acres are directly adjacent to the Windham Country Club, which features a public 18-hole public golf course, as well as the local favorite hiking trail, Windham Path. A restored vintage Land Rover Defender 110 Shuttle provides complimentary rides to those looking to venture a bit further off-site to experience local institutions such as Windham Fine Arts and The Vineyard at Windham.

LINK TO BOOK: https://wylderhotels.com/windham/

Top Takeaways:

Location: Windham, NY

Rating: Four-Star Hotel

The Vibe: As a reimagination of an iconic 20-acre resort dating back to the 1800s, each of the historic lodges embody the outdoorsy, nostalgic, and inviting character of the Great Northern Catskills. 

Food + Drink: Babblers Restaurant, Bar & Bakery is the versatile all-day watering hole. Situated next to the Batavia Kill creek, this spot is inherently laid black and approachable. The bakery serves tasty treats to stay or go ranging from coffee, fresh croissants, artisanal breakfast sandwiches, and homemade pies. The restaurant and bar serve spirited libations that perfectly pair with signature dishes such as Chicken & Biscuits, Old School Fish Fry, and Not Your Mother’s Meatloaf.

Property Amenities: Outdoor pool; Bicycles available; Pet-friendly; Yoga classes; Pickleball courts; Free parking

Our Favorite Thing About the Hotel: The property offers two wood-fire saunas, both of which are strategically positioned to enjoy views of Windham Mountain. To ensure they’re nice and toasty upon arrival, be sure to book them in advance, ideally around sunset for the most breathtaking scenes.

What’s Nearby?: Windham Path; Windham Mountain; The Vineyard at Windham; Ze Windham Wine Bar; Five State Lookout; Bistro Brie & Bordeaux

Any Neighborhood Recs?: Coordinate a ride with Dawn 2 Dusk Car Service over the mountain to Deer Mountain Inn. The hotel’s restaurant comes highly recommended by the Wylder Hotel Windham team; the property evokes ski lodge vibes, with printed wallpaper, antique furnishings, and paintings of wildlife and deer heads hanging on the walls. Everything on the menu is sourced entirely from local, regenerative farms, and the selection rotates on a monthly basis. 

Rooms: 110

Starting Nightly Rate: $340

Closest Airport: Albany International Airport

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